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OSMANIA UNIVERSITY LIBRARY
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PHYSICAL CONSTANTS
OF HYDROCARBONS
Volume II
CYCLANES, CYCLENES, CYCLYNES,
and
OTHER ALICYCLIC HYDROCARBONS
GUSTAV EGLOFF
DIRECTOR OF RESEARCH
UNIVERSAL OIL PRODUCTS COMPANY
RESEARCH LABORATORIES
CHICAGO, ILLINOIS
American Chemical Society
Monograph Scries
REINHOLD PUBLISHING CORPORATION
330 WEST FORTY-SECOND STREET, NEW YORK, U. S. A.
1940
COPYRIGHT, 1940, Bv
REINTIOLD PUBLISHING CORPORATION
All rights reserved
Printed in the United States of America by
INTMNATIONAL TEXTBOOK PBESS, BCBANTON, PA.
Dedicated to
JOSEPH G. ALTHER
GENERAL INTRODUCTION
American Chemical Society Series of
Scientific and Technologic Monographs
By arrangement with the Interallied Conference of Pure and Applied
Chemistry, which met in London and Brussels in July, 1919, the American
Chemical Society 8 was to undertake the production and publication of
Scientific and Technologic monographs on chemical subjects. At the same
time it was agreed that the National Research Council, in cooperation with
the American Chemical Society and American Physical Society, should
undertake the production and publication of Critical Tables of Chemical
and Physical Constants. The American Chemical Society and the National
Research Council mutually agreed to care for these two fields of chemical
development. The American Chemical Society named as Trustees, to make
the necessary arrangements for the publication of the monographs, Charles
L. Parsons, secretary of the society, Washington, D. C. ; the late John E.
Teeple, then treasurer of the society, New York; and Professor Gellert
Alleman of Swarthmore College. The Trustees arranged for the publica-
tion of the A. C. S. series of (a) Scientific and (b) Technologic Mono-
graphs by the Chemical Catalog Company, Inc. (Reinhold Publishing Cor-
poration, sviccessors) of New York.
The Council, acting through the Committee on National Policy of the
American Chemical Society, appointed editors (the present list of whom
appears at the close of this introduction) to have charge of securing
authors, and of considering 1 critically the manuscripts submitted. The
editors endeavor to select topics of current interest and authors recognized
as authorities in their respective fields.
The development of knowledge in all branches of science, especially in
chemistry, has been so rapid during the last fifty years, and the fields cov-
ered by this development so varied that it is difficult for any individual
to keep in touch with progress in branches of science outside his own
specialty. In spite of the facilities for the examination of the literature
given by Chemical Abstracts and by such compendia as Beilstein's Hand-
bitch der Organischen Chemie, Richter's Lexikon, Ostwald's Lehrbuch der
Allgemeinen Chemie, Abegg's and Gmelin-Kraut's Handbuch der Anor-
ganischen Chemie, Moissan's Traite de Chimie Minerale Generate, Friend's
and Mellor's Textbooks of Inorganic Chemistry and Heilbron's Dictionary
of Organic Compounds, it often takes a great deal of time to coordinate
5
6 PHYSICAL CONSTANTS OF HYDROCARBONS
the knowledge on a given topic. Consequently when men who have spent
years in the study of important subjects are willing to coordinate their
knowledge and present it in concise, readable form, they perform a service
of the highest value. It was with a clear recognition of the usefulness of
such work that the American Chemical Society undertook to sponsor the
publication of the two series of monographs.
Two distinct purposes are served by these monographs : the first, whose
fulfillment probably renders to chemists in general the most important
service, is to present the knowledge available upon the chosen topic in a
form intelligible to those whose activities may be along a wholly different
line. Many chemists fail to realize how closely their investigations may
be connected with other work which on the surface appears far afield from
their own. These monographs enable such men to form closer contact
with work in other lines of research. The second purpose is to promote
research in the branch of science covered by the monograph, by furnishing
a well-digested survey of the progress already made, and by pointing out
directions in which investigation needs to be extended. To facilitate the
attainment of this purpose, extended references to the literature enable
anyone interested to follow up the subject in more detail. If the literature
is so voluminous that a complete bibliography is impracticable, a critical
selection is made of those papers which are most important.
AMERICAN CHEMICAL. SOCIETY
BOARD OF EDITORS
Scientific Series : Technologic Series :
WILLIAM A. NOYES, Editor, HARRISON E. HOWE, Editor,
S. C, LINO, WALTER A. SCHMIDT,
W. MANSFIELD CLARK, E. R. WEIDLEIN,
LINUS C. PAULING, F. W. WILLARD,
L. F. FIESER. W. G. WHITMAN,
C. H. MATHEWSON,
THOMAS H. CHILTON,
BRUCE K. BROWN,
W. T. READ,
CHARLES ALLEN THOMAS.
Preface
The alicyclic hydrocarbons are available in nature to an enormous extent.
Petroleum is the greatest potential source of the cyclanes or cycloparaffins (naph-
thenes). The oil production of the world for 1939 was about 2,000,000,000 barrels,
of which 500,000,000 were cyclane hydrocarbons. This volume of cyclanes was
largely consumed as motor fuel, kerosene, gas oil, Diesel oil, lubricants, and as
fuel for household and industrial use.
A new chemical industry could well be developed based upon cyclane chemistry,
to which very little research has been directed. At the moment a new chemical
industry is being founded in the aliphatic hydrocarbons derivable from petroleum
and natural gas. The chemistry of the cyclenes through essential oils and their
polymerization has been studied through the years.
The collation of the physical constants, melting point, boiling point, specific
gravity, and refractive index of the alicyclic hydrocarbons has been made in order
to facilitate and energize research for chemical derivatives of scientific and utili-
tarian use in this potentially fruitful field.
The author deeply appreciates the assistance of his colleagues, Dr. J. Sherman,
Prudence M. Van Arsdell, Dr. R. B. Dull, Dorothy V. Nordman, Dorothy Sigman,
and Mary Alexander in this collation and critical study of the physical constants
of the alicyclic hydrocarbons.
GUSTAV EGLOFF
February 15, 1940
Physical Constants of Hydrocarbons
Cyclanes, Cyclenes, Cyclynes, and Other Alicyclic Hydrocarbons
TABLE OF CONTENTS
Volume II
Page
General Introduction 5
Preface 7
I. Introduction 13
1. Foreword 13
2. Structure of Alicyclic Hydrocarbons 13
A. Introduction 13
B. General Considerations 14
C. Monocyclic Rings of the Alicyclic Series 16
1. Cyclopropane, Cyclobutane and Cyclopentane 16
2. Cyclohexane 16
Cyclanes Containing Fused (Shared) Rings 17
Alicyclic Hydrocarbons Containing Double and Triple Bonds 18
Geometrical Isomerism 18
3. Nomenclature of Alicyclic Hydrocarbons 19
A. Introduction 19
B. Geneva Nomenclature 20
1. Introduction 20
2. Rules and Author's Comments 20
a. Monocyclics 20
b. Polycyclics 22
C. Definition of Bi and Di in Alicyclic Nomenclature 29
D. Supplementary Nomenclature Considerations 30
4. Critical Evaluation of the Data and Calculation of the Most Probable Values 35
A. Introduction 35
B. Melting Point 35
C. Boiling Point 36
D. Specific Gravity 36
E. Index of Refraction 37
5. Description of the Tables 37
A. Structural Formulae 37
B. Introduction to Tables 39
9
10 PHYSICAL CONSTANTS OF HYDROCARBONS
Page
II. Cyclanes or Cycloparaffins 41
1. Cyclanes with Alkyl Substitutions, C B H 2n 42
2. Cyclanes with an Alkenyl or Olefin Substitution, CH 2n - 2 150
3. Cyclanes with two Alkenyl or Olefin Substitutions, CH Sn _4 179
4. Cyclanes with an Alkadienyl or Diolefin Substitution, C n H 2n _.4 183
5. Cyclanes with an Alkynyl or Acetylene Substitution, CH 2n _4 185
6. Cyclanes with a Cycloalkenyl or Cycloolefin Substitution, CH 2n _ 4 190
7. Cyclanes with a Bicyclenyl or Bicycloolefin Substitution, C n H 2B ..6 195
III. Dicyclanes or Dicycloparaffins 197
IV. Tri, Tetra, and Penta Cyclanes 219
CnH 2n -8
V. Bicyclanes or Bicycloparaffins 229
1. Bicyclanes with Alkyl Substitutions, C n H 2 n-2 231
2. Bicyclanes with an Alkenyl or Olefin Substitution, C n H 2n _4 264
3. Bicyclanes with two Alkenyl or one Alkadienyl Substitution, CH 2n -ft 275
VI. Tricyclanes Endocyclic 277
CnH 2n -4
VII. Polycyclanes or Polycycloparaffins (Fused Rings) 291
1. Polycyclanes with Alkyl Substitutions, C n H 2n _ 293
2. Polycyclanes with an Alkenyl or Olefin Substitution, C n H 2n > 8 302
VIII. Cyclene or Cycloolefins 303
1. Cyclene with Alkyl Substitutions, CH 2 _ 2 305
2. Cyclenes with an Alkenyl or Olefin Substitution, C n H 2n ~4 366
3. Cyclenes with two Alkenyl or one Alkadienyl Substitution, C n Hi n _ 397
4. Cyclenes with Alkene-Alkyne or Alkatriene Substitution, C n H 2n 8 400
IX. Cyclodienes or Cyclodiolefins 401
1. Cyclodienes with Alkyl Substitutions, CH 2n _4 403
2. Cyclodienes with an Alkenyl or Olefin Substitution, CnH 2 -6 431
X. Cyclotrienes or Cyclotriolefins (Exclusive of Aromatics), 439
XL Dicyclenes or Dicycloolefins 443
1. Dicyclenes with Alkyl Substitutions, C n Hi- 445
2, Dicyclenes with an Alkadiene or an Alkyne Substitution, C n H 2n ..io 450
XII. Bicyclenes or Bicycloolefins 451
1. Bicycienes with Alkyl Substitutions, C n H 2n -4 453
2. Bicyclenes with an Alkenyl Substitution, C w Hm-. 477
TABLE OF CONTENTS 11
Page
XIII. Bicyclodienes or Bicyclodiolefins 481
XIV. Di(bicyclenes) or Dibicycloolefins 491
C n H 2 n-10
XV. Polycyclenes 49S
CnHjn-e
XVI. Cyclynes or Cycloacetylenes 501
C n H 2n -4
XVII. Spiro Hydrocarbons 505
XVIII. Alicyclic Hydrocarbons of Known but Unclassified Structures 511
XIX. Alicyclic Hydrocarbons of Undetermined Structure (Thought to
belong to the Naphthene or Cyclic Series) 537
I. Introduction
1. Foreword
The present volume is the second of a four-volume work on the collation and
systematic study of the physical constants of all classes of pure hydrocarbons.
Volume I, which was published in March 1939, includes the paraffins, olefins,
acetylenes, and other aliphatic compounds. The physical constants of the cyclanes
or cycloparaffins, cyclenes or cycloolefins, and other alicyclic compounds are
reported in Volume II. All cyclic hydrocarbons containing nonaromatic rings
have been critically evaluated in this study. The literature and our own and other
experimenters' work have been reviewed in order to present all the data which has
been available to March 1939.
In comparing the alicyclic hydrocarbons with those of the aliphatic series, it
may be pointed out that the former group has not been as extensively studied as
the latter as regards physical constants. This is due, in part, to the fact that the
aliphatic hydrocarbons have been of more scientific and industrial importance for
a longer time than the alicyclic compounds.
The data on the four physical constants melting point, boiling point, specific
gravity, and index of refraction of the liquid hydrocarbons are more inconsistent
for the alicyclic than for the aliphatic hydrocarbons. The greater difficulty of
preparing pure alicyclics probably accounts for this, and also the constants reported
in many cases are for mixtures of geometrical isomers rather than individual com-
pounds. A further difficulty in obtaining precise physical constant values for a
number of alicyclic hydrocarbons is that they may partially isomerize while the
determination is being made due to catalytic influences of the apparatus.
The greater inaccuracy of the alicyclic constants is evidenced by the adopted
values of the constants, which are given to fewer significant figures than is the case
for the aliphatics. The specific gravity and index of refraction values are given to
three significant figures in almost all cases as compared to four and five for the
aliphatic compounds.
In contrast to the studies which have been made by various workers in correlat-
ing physical constants of aliphatic hydrocarbons, almost nothing of this character
has been carried out for the alicyclic hydrocarbons.
2. The Structure of Alicyclic Hydrocarbons
A. INTRODUCTION
Although much experimental and theoretical work has been done in recent
years in order to determine the structures of alicyclic hydrocarbons, the problem
cannot be regarded as solved up to the present time (August 1939). The term
structure is used here to denote the relative positions of the atomic nuclei in the
molecule and not the electronic structure.
13
14 PHYSICAL CONSTANTS OF HYDROCARBONS
The fundamental postulate concerning the tetrahedral structure of a carbon
atom 'stated by LeBel and van't Hoff in order to explain optical isomerism was
also a method of presenting a valid picture of stereochemistry until the discovery of
cyclic compounds in nature and in the laboratory. Due to this discovery, the idea
of the rigid tetrahedral angle of 109 28' was necessarily modified. The six-mem-
bered ring of the alicyclic group was the first to be prepared and since the other
members of the series, cyclopropane, cyclobutane, cyclopentane and others higher
than cyclohexane were unknown in nature, and impossible to synthesize by labora-
tory methods in use before 1880 1 , it was argued that they did not exist due to
theoretical considerations then generally accepted.
A compound containing a cyclobutane ring and the discovery of cyclopropane
between 1880 and 1885 led to the modification of the ideas concerning the existence
and possible stability of the cyclic compounds, and in 1885 Baeyer 2 proposed the
strain theory to explain the relative stabilities of cyclopropane, cyclobutane, cyclo-
pentane, and cyclohexane. His theory, however, did not explain the existence of
the higher ring compounds.
Since the time of Baeyer, the higher ring compounds have been synthesized
and a theory for strainless ring structures 3 has been developed which will be dis-
cussed later.
B. GENERAL CONSIDERATIONS
One of the fundamental postulates of structural organic chemistry is that the
angles between the carbon-carbon bonds in a saturated hydrocarbon molecule are
tetrahedral. Many facts accumulated through the years support this postulate.
Within recent years the tetrahedral nature of the carbon atom in a few simple
cases has been directly verified by experiments determining the crystal structure of
hydrocarbons by x-ray diffraction, by electron diffraction of gases, and by spectro-
scopic analysis. Evidence has also accumulated showing that the radius of the
carbon atom in saturated compounds is nearly constant at 0.77 A. (the bond dis-
tance between two atoms is equal to the sum of the atomic radii). If this were not
so, then planar rings having tetrahedral angles could be constructed having more
carbon atoms than cyclopentane. Bond angles in saturated ring compounds
should be tetrahedral, just as in aliphatic hydrocarbons. For cyclopropane and
cyclobutane and many other compounds containing fused rings such as carene or
bicyclohexane this is geometrically impossible.
It is possible to construct a six-membered ring, cyclohexane, in which the
carbon-carbon bond distances are equal, and the angles all tetrahedral; hence the
ring will not be planar. This was clearly pointed out by Sachse 4 and later elab-
orated upon by Mohr 5 in order to show that rings containing more than five carbon
atoms need not be strained as Baeyer believed. It remained for Cohen-Henriquez 6
(1) Meyer, Ann., 180, 192, 1876
(2) Baeyer, Ber., 18, 2278, 1885
(3) Ruzicka, Stoll, Huyser, and Boekenqogen, Helv. Chim. Acta, 13, 1152, 1930
(4) Sachse, Bcr., 23, 1363, 1890
(5) Mohr, J. prakt. Chem. (2), 98, 349, 1918
(6) Cohen-Henriquez, Proe. Roy. Acad. Amsterdam 3V, 532, 1934
INTRODUCTION 15
to give a thorough mathematical treatment of the cyclohexane problem. He
showed that it is possible to construct not only one but an infinite set of strainless
cyclohexane rings. One of the members of this set, the so-called chair form of
cyclohexane, is a singular one in that it cannot be derived from any of the others
by a simple Distortion not accompanied by a change in the bond angles. The other
members of the set, of which the boat form is representative, can all be obtained
from any one of them by twisting, not accompanied by bond angle change.
The point of chemical interest in this discussion is that if many forms of cyclo-
hexane actually exist, then it should perhaps be possible to separate isomers cor-
responding to some of the different possibilities. What is even more pertinent to the
present study is the wide variation in the physical constants of cyclohexane reported
by investigators, which ^may in part be attributed to a partial or even complete
separation of the boat and chair forms, and similarly for other alicyclic compounds.
As a matter of fact, claims are made from time to time that such isomers have been
separated. The most recent claim to the separation of the forms of methylcyclo-
hexane is that reported by Vogel 7 . These results have been disputed by Wibaut,
Langedijk, Smittenberg, and Hoog 8 ; hence further studies should be made.
Although it is apparently impossible to separate the chair and boat forms of
cyclohexane in the liquid state, the x-ray diffraction study of the structure of the
crystals strongly indicate that the molecules are of the chair form.
In order to reconcile theory and experimental facts, it has been suggested that
the possible forms of cyclohexane are in rapid equilibrium so that the statistical
average corresponds to a plane structure. If it is assumed that cyclohexane
oscillates between the chair and boat forms (the boat form is used here collectively
to signify all the structures which may be derived from it by simple distortion), the
low frequency of oscillation must be of negligible importance in increasing the
stability relative to the individual forms. Also, it is by no means obvious that the
activation energy in the conversion of the boat to the chair form is negligibly small.
The bond distances are more important in determining the structure than the
bond angles, since it requires considerably more energy to change the normal
carbon-carbon single bond distance a small amount than it does to change the bond
angle.
Let us now consider the geometrical problem of determining how many forms
of an equilateral, equiangular polygon of n sides may be constructed from a set
of n points located at the vertices. The general case is extremely difficult and has
not been treated. An equilateral, equiangular polygon of n sides may be con-
structed in which the sides are of any given length. However, the angles must
have an average value equal to or less than ( )TT, If the angles in the ring are
\ n /
each equal to the upper limit of ( JTT, the ring is a planar one, and there is one
and only one such ring which can be constructed. If, however, the angles are
(H 2\
W, the regular polygon will not be a plane. Moreover, as Cohen-
n /
(7) Vogel, J. Chem. Soc., 1938, 1323
(8) Wibaut, Langedijk, Smittenberg, and Hoog, Chem, and Ind., 57, 753, 1938
16 PHYSICAL CONSTANTS OF HYDROCARBONS
Henriquez showed for cyclohexane, it will, in general, be possible to construct
more than one such polygon for a given value of the angle.
Since two single bonds associated with a carbon atom which is part of a double
bond tend to be at 120 angles to the double bond, and since the carbon-carbon
double bond distance is about 14 per cent shorter than the carbon-carbon single
bond distance, the introduction of one or more double bonds into a saturated ring
will tend to change the ring configuration to some extent.
C. MONOCYCLIC RINGS OF THE ALICYCLIC SERIES
1. Cyclopropane, Cyclobutane, and Cyclopentane
The equilibrium positions of the carbon nuclei in each of these molecules are
located at the vertices of an equilateral triangle, a square, and a regular pentagon
respectively. The four carbon nuclei in cyclobutane are not geometrically required
to lie in a plane. However, they probably are coplanar, for otherwise the average
bond angle would be less than 90, and the molecule would be less stable than the
plane form.
In each of the cyclopropane, cyclobutane, and cyclopentane molecules, the two
hydrogen bonds associated with each carbon are probably at the tetrahedral angle
to each other, the plane of the bonds being perpendicular to the plane of the ring
and bisecting the pertinent carbon bond angle.
2. Cyclohexane
Reference has already been made to the work of Cohen-Henriquez in which it
was shown by methods of analytical geometry that there are an infinite number of
possible cyclohexane rings in which the bond distances are all equal and the bond
angles all tetrahedral. The configuration of any one possibility may be described
by reference to the following figure :
Since the bond distances and bond angles are to remain fixed, the large triangle BDF
will remain invariant to all permissible forms of the cyclohexane ring.
Let 0j, <fo, and 8 denote the angles which the small triangles ABF t BDC, and
DBF make with the plane of the triangle BDF respectively. The configuration of
the ring is completely specified when the values of the three angles 0i, <fe, and #3 are
given. For the "fixed" or chair configuration
0! - 02 - 0s - cos - l (Vf ) - * 35 (approx.)
INTRODUCTION 17
The following figures depict the boat and chair forms respectively:
boat form chair form
In each of these two forms there are four carbon atoms in a plane at the corners of
a rectangle. In the boat form, the remaining two carbon atoms are both on the
same side of the plane of the other four, and in the chair form, the two carbon atoms
not in the plane of the other four are on opposite sides of this plane. For this
reason, the boat form is sometimes referred to as the cis and the chair type as the
trans form.
D. CYCLOPARAFFINS CONTAINING FUSED RINGS
The carbon skeleton of the molecule [0,2,2]-bicyclohexane is usually written as
. Corresponding to this drawing, it may be described as the boat form
of cyclohexane in which the 1,4-carbon atoms are bonded to each other. If the
cyclohexane ring were undistorted, this bond would be f 1.67 times as long as the
bonds in the ring. (The 1 ,4- atoms in the chair form of cyclohexane are $ -\[33 1 .915
times as far apart as the adjacent atoms in the ring, and a bond in this case would
be even weaker than in the case being considered). Moreover, the two cyclobutane
rings would be isosceles trapezoids in which two of the angles were tetrahedral and
two of the angles 70 32'. But from the structural principles already elaborated,
it may be concluded that in [0,2,2]-bicyclohexane the 1,4- bond is not appreciably
different from the other carbon-carbon bonds in the ring, and that the carbon
skeleton consists of two cyclobutane rings (squares) the planes of which are inclined
to each other at approximately the tetrahedral angle.
It is believed that [0,2,2]-bicyclohexane reacts rather readily to form derivatives
of cyclohexane; and this is sometimes given as evidence that the 1,4- bond in the
bicylohexane is much weaker than the other carbon bonds. This argument is
unreliable for the following reasons: if one of the carbon-carbon bonds in the
bicyclohexane is broken, e.g., by the addition of hydrogen, the possible products
are 1,2-dimethylcyclobutane, ethylcyclobutane, and cyclohexane. Cyclohexane
is the most stable of these hydrocarbons; hence it is formed, assuming, of course,
that the activation energy of this reaction is less than for the other reactions.
The foregoing discussion for [0,2,2]-bicyclohexane brings out certain general
features of the structure of shared rings. This compound (as well as all other "bi"
cyclocompounds) really contains three rings two cyclobutane rings having a side
in common, and a cyclohexane ring, three sides of which are common to one of the
18 PHYSICAL CONSTANTS OF HYDROCARBONS
cyclobutane rings and the other three sides to the other. The smaller rings are
more important from energy considerations than the large one, i.e., the cyclo-
butane rings tend to be squares at the expense of the regular cyclohexane ring.
Similar considerations apply to other rings. For example [0,l,3]-bicyclohexane
may be written as a cyclohexane with a bond between the 1,3-atoms; however, it
is more nearly a regular pentagon and an equilateral triangle sharing a side, the
plane of the triangle being inclined to the plane of the pentagon at the tetrahedral
angle.
E. ALICYCLIC HYDROCARBONS CONTAINING DOUBLE AND TRIPLE BONDS
Cyclopropene has not been synthesized as yet. This is not surprising, for a
consideration of the bond angles involved shows that cyclopropene would be
highly unstable.
Cyclobutene is known, but not cyclobutadiene. The small increase in stability
that would result from the resonance energy in the latter case is not sufficient to
offset the instability due to 90 bond angles between conjugated bonds.
The introduction of one or two double bonds in the cyclohexane ring causes it
to assume a configuration intermediate between benzene and cyclohexane.
In a very few cases rings containing triple bonds have been reported. These
compounds would probably be unstable.
In the discussion of the structure of alicyclic ring hydrocarbons, it was assumed
that the general structural features of these rings are determined by the carbon-
carbon bond distances and the carbon-carbon bond angles. This is only an approxi-
mation. Other factors may be of significance e.g., the van der Waals* forces,
the zero-point energy, and particularly the interaction of the carbon-hydrogen
bonds with the carbon-carbon bonds in the ring 9 . Studies on the last factor are
being made and will be reported in the fourth volume of this study of the physical
constants of hydrocarbons.
F. GEOMETRICAL ISOMERISM
In the study of aliphatic hydrocarbons, it was pointed out that geometrical
isomerism in the olefins occurs whenever a 180 rotation about the double bond
of one of the two groups attached by the double bond would result in a molecular
configuration which could not be converted to the original by any rotations of the
molecule as a whole; e.g., butene-2 has two geometrical isomers, the as-butene-2
has the structure c^ ^ ^* whereas the Jrans-butene-2 has the structure
TT /"*
r X c " aC C. This group isomerism is due partly to the inability of rotation
c *i
to take place about the double bond. In the alicyclic compounds geometrical
isomerism also occurs for an additional reason the lack of rotation about carbon-
carbon single bonds which are part of a ring system. Geometrical isomerism in
the alicyclic compounds is, consequently, a more prevalent phenomenon than in the
aliphatic compounds.
(9) Cohen, Kistiakowsky, and Smith, /. Am. Chem. Soc. t 61, 1870, 1939; Govin, Walter, and
Eyring, *to** 61, 1876, 1939
INTRODUCTION 19
Since geometrical isomers possess different physical properties their constants
should be evaluated separately. In a few cases, the investigator has explicitly
stated that his compound is cis or trans, and these have been listed as such in the
tables. In the majority of cases where geometrical isomers are theoretically
possible, the physical constants are reported without mention by the experimenter
as to whether his compounds are the pure cis or pure trans isomer or some mixture
of these. In accordance with the procedure of tabulating the constants adopted
for the aliphatic olefins, the alicyclic constants are listed, but no effort was made
to obtain an average value for possible mixtures of cis and trans isomers.
As has already been discussed in the section on structure, geometrical isomerism
is a complicated phenomenon in the alicyclic compounds. Except for the simpler
cases it is not usually possible to state definitely how many isomers are possible.
Almost all the shared rings can exhibit geometrical isomerism, and therefore, the
constants for these compounds have been evaluated in only a few cases.
The possibilities of geometrical isomerism become quite complex in shared
ring systems. Cohen-Henriquez investigated the perhydronaphthalene ring and
found that several fixed and mobile configurations are possible. Actually per-
hydronaphthalene has been separated into cis and trans isomers having different
physical constants. In other shared ring systems, the physical constants are,
with few exceptions, reported without mention of the possibility of geometrical
isomerism.
3. Nomenclature of Alicyclic Hydrocarbons
A. INTRODUCTION
The nomenclature of alicyclic hydrocarbons is in a confused state due to the
many terms and numbering systems used. In some cases the same experimenter
has named and numbered the alicyclic hydrocarbons several ways in the same
publication without explanation. The nomenclature rules for this series of hydro-
carbons are not as extensive, and in some cases not so clearly defined as those used
for the aliphatic compounds. An attempt has been made in the present study to
bring about uniformity in the numbering and naming of the alicyclic hydrocarbons.
The saturated cyclic compounds were originally called polymethylenes and the
term still persists due to the chemical formulae being multiples of methylene, Each
compound was named by means of the Greek numerical prefix plus methylene,
hence cyclopentane was first known as pentamethylene. Several disadvantages
of this naming system developed as work progressed in alicyclic chemistry. The
term polymethylenes was too inflexible to be of value due to the fact that the term
applied only to the single ring saturated structures.
Other terms applied to alicyclic hydrocarbons and widely used are naphthenes,
hydroaromatics, and terpenes. The terpene classification has been omitted from
separate consideration in this study, since it is recognized that the members of this
group are classified in their proper alicyclic series. The terpene names have
been retained in addition to the systematic ones assigned in the Geneva system.
In so arranging the terpenes, it is hoped that structural relationships will be shown
throughout the different series rather than for individual compounds in the usual
terpene groupings. Although there are generic group names given to the naph-
20 PHYSICAL CONSTANTS OF HYDROCARBONS
thenes, polymethylenes, and hydroaromatics, they are not classified under these
terminologies.
The disadvantages imposed by such names as polymethylenes, naphthenes,
hydroaromatics, and terpenes are overcome by the more systematic terms which
include cyclanes, cydoalkanes, or cycloparaffins; cyclenes, cycloalkenes, or cyclo-
olefins; cyclynes, cycloalkynes, or cycloacetylenes. Chemical Abstracts 10 uses the
terms cyclanes, cycloalkanes, cycloparaffins, and naphthenes to cover the cyclic
hydrocarbons of the general formula CH2 n .
In this study of the physical constants of alicyclic hydrocarbons, the terms
cyclanes, cyclenes, and cyclynes are used genetically for the monocyclic compounds
due to the simplicity of the terms compared to the others which have been used.
B. GENEVA NOMENCLATURE
1. Introduction
The rules used in this study were obtained in part from the Definitive Report
of the Commission on the Reform of Nomenclature of Organic Chemistry and
the Council of the International Union of Chemistry 11 . The data in Beilstein were
also used where the Geneva rules were not sufficient. These two sources of nomen-
clature generalizations were found insufficient for the complete study and were
supplemented by the author.
2. Rules and Author's Comments
a. Monocydics
The following rules 11 are quoted from the Definitive Report ;
"11. Saturated monocyclic hydrocarbons will take the names of the cor-
responding straight chain saturated hydrocarbons, preceded by the prefix 'cycle'
They will bear the generic term cycloalkanes."
Author's note. In this study the term cyclanes has been used instead of cycloalkanes.
"13. When they (alicyclics) are unsaturated Rules 8 and 9 will be applied.
However, in the case of partially saturated polycyclic aromatic compounds, the
prefix hydro preceded by di-, tri-, tetra-, etc., will be used. Example Dihydro-
anthracene."
Author's note. The Geneva 11 Rules 8 and 9 have been adapted on the basis of Rule 13 so as
to apply to the alicyclic hydrocarbons.]
Rule 8. In the names of unsaturated cyclic hydrocarbons having one double bond, the end-
ing -ane of the corresponding saturated hydrocarbon will be replaced by the ending -ene; if there
are two double bonds, the ending will be -diene, etc. These hydrocarbons will bear the generic
names cyclenes, cyclodienes, cyclotrienes t and cyclotetraenes except in aromatic structures,
Rule 9. The names of triple bond cyclic hydrocarbons will end in -yne. They will bear the
generic names cyclynes.
(10) Chem. Abs., Index, 1938
(11) Patterson, /. Am. Chem. Soc. t 55, 3905, 1933
INTRODUCTION 21
"Rule 49aP. Cyclic hydrocarbons with aliphatic side chains are to be named
according to one of the two following methods: (a) The radical names denoting
the side chains are prefixed to the name of the cyclic hydrocarbon, (b) The cyclic
hydrocarbon residue, if it can be named as a radical, is considered a substituent of
the aliphatic chain. 12
"Naming according to (a) is in general preferable when the side chain is short
or when several side chains are present. Naming according to (6) is more con-
venient when the side chain is long, and particularly when the cyclic hydrocarbon
residue is not at the end of this chain."
Author's examples:
c
1 -Methyl-2-ethylcyclohexane 1 ,3-Dimethyl-2~ethenylcyclohexane
"When several cyclic hydrocarbon residues are united by an aliphatic chain
the name of the compound will be derived from that of the aliphatic hydrocarbon,
provided radical names are available for the cyclic hydrocarbon residues. "
Author's example:
/ \-C-C-C-C-C-C-/ \
1 ,6-Dicyclohexylhexane
The following rules for numbering and presentation of the various ring systems
used throughout this study of alicyclic hydrocarbons are taken from the "Proposed
International Rules for Numbering" 12 .
The adaptations of the rules with explanations of the changes necessary in this
study, together with present practices are given in Chemical Abstracts Index for
1938. Only those rules which may apply to the alicyclic hydrocarbons are reported
here 13 despite the fact that the rules are not specific enough.
"A. THE SYSTEM CONSISTS OP A SINGLE RING
I. The ring is carbocydic
Rule 1. "Number around the ring in such a manner as to give to hydrogen
atoms the lowest numbers possible.
(12) Latest text adopted at Lucerne 1936, and confirmed in Rome, 1938, Science, 87, No. 2253
216. 1938
(13) Patterson, J. Am. Chem. Soc., 47, 543, 1925, Chem. Abs. t Index, 1938
22
PHYSICAL CONSTANTS OF HYDROCARBONS
"Examples:
CH 2
CH
HC
HC
CH
CH
"Note 4. Fixed orientations are an aid to memory and should not be neglected.
Single rings should be oriented with Position 1 at the top and with numbers pro-
ceeding clockwise around the ring/'
Author's note: The latest Chemical Abstracts practice 10 regarding the bond placement in the
ring reverses Rule 1 and gives the double bond the lowest number possible rather than the hydro-
gen previously shown.
Example:
CH
H 2 C
CH
CH 2
This is in line with the rule covering aliphatic hydrocarbons where the lowest number is given
to the double or triple bond when they appear singly in the compound. It is more convenient in
this study to follow this system for the ring compounds instead of Rule 1.
In the six membered cyclodiolefins there are three positions possible for the bonds, the 1 ,2 ;
1,3 and 1,4; the substituting groups are oriented with higher or lower numbers in respect to the
double bonds.
Examples:
CH
CH
H,C
A cyclodiolefin of 1,2 structure as shown has been reported and the constants shown in the
tables, although there is doubt as to the existence of such a compound.
Examples Ilia, III&, and lllc are used throughout our study and supplant Examples II and
III of Rule 1 made in 1925.
b. Polycyclics
"B. THE SYSTEM CONTAINS AT LEAST Two RINGS OF FIVE OR MORE MEMBERS,
BUT NO ATOMIC BRIDGES, CROSSED VALENCE BRIDGES OR FREE SPIRO UNIONS
"Note 6. An 'atomic bridge* is one that contains atoms (e.g., the bridge in
norcamphane, V) as contrasted with a Valence bridge* (e.g., that in naphthalene,
VI, or in norcarane, VII).
INTRODUCTION
23
CH 2
CH
r
7CH 2
CH
H 2 C
CH 2
CH
V
VI
VIII
"Note 7. 'Crossed valence bridges' are valence bridges that are represented
by the plane formula as crossing each other as shown in Example XLVIII.
H 2 C
"Note 8. A 'spiro union 1 is one formed by a single atom which is the only
common member of two rings. A 'free spiro union* is one constituting the only
union direct or indirect, between two rings as in IX. Systems in which the rings
are united in some other way (that is by intermediate rings) as well as by the spiro
union are not necessarily excluded from Class B.
H 2 c
"Note 9. In determining whether or not a system contains at least two rings
of five or more members, one counts as component rings only the smallest number of
smallest rings that together will account for all the atoms and valences.
4 "Rule 6. Orient the formula so that the greatest possible number of rings
will be in a horizontal row.
"Note 10. Triangles in such a row should have one side vertical, other rings
two sides vertical (this requires a deformation of the polygons with an odd number
of sides, thus :
or
). Accordingly, hexagons should have angles, not
sides, at top and bottom. Anthracene (XIII) constitutes a horizontal row of three,
so do fluorene (XIV) and s-indacene (XV), but phenanthrene (XVI) does not."
24
PHYSICAL CONSTANTS OF HYDROCARBONS
XIII
XIV
XV
XVI
Author's note: The use of regular polygons such as a regular pentagon for cyclopentane, etc.,
have been used in the tabulated data since it is thought that these structural configurations more
nearly represent the equilibrium position of the atoms in the molecule.
"Rule 7. Of orientations conforming to Rule 6, choose the one that places as
many as possible of the remaining rings above and to the right.
"Note 11. Only the number of rings and not their size or distance from the
center, is taken into account. When the correct orientation is not immediately
apparent, bisect the 'horizontal row* by a horizontal axis and a vertical axis (as in
XXI) and count the rings and fractions of rings in the four quadrants. If there is
more than one combination of rings that could serve as the 'horizontal row,' apply
the bisection in the other cases also (as in XXII). Choose the orientation that
has as many as possible of the 'remaining rings' in the upper right quadrant; if two
or more orientations meet this requirement, choose the one of them that has as
few rings as possible in the lower left quadrant. In the examples, phenanthrene
(XVI) is shown correctly oriented with its single 'remaining ring* turned upward
toward the right; triphenylene (XVII) has one in the upper right quadrant and
one in the lower right; Examples XVIII-XX show right and wrong orientations
of chrysene; and XXI and XXII show right and wrong orientations in a case that
might not be immediately apparent.
XVII Triphenylene
XVIII (right) Chrysene
XIX (wrong)
INTRODUCTION
25
XX (wrong)
XXI (right)
XXII (wrong)
"Rule 10. Of orientations conforming to Rules 6-9, choose the one in which
unnumbered carbon atoms follow the lowest numbers possible.
"Examples: In XXIX the unnumbered carbon atoms follow the numbers 4,4,8,9; these are
lower than the 4,5,9,9 of XXX. Similarly, the numbers 2,5,8 of XXXI are lower than the 3,5,8
of XXXII.
XXIX (right)
XXX (wrong)
XXXI (right) XXXII(wrong)
"Rule 11. Of orientations conforming to Rules 6-10, choose the one that
gives to hydrogen atoms the lowest numbers possible.
"Rule 12. Number the oriented formula by beginning with the first free angle
of the upper right ring and proceeding clockwise around the entire formula to the
beginning, numbering all carbon atoms that are not common to two or more rings.
XXXIII
XXXIV
26
PHYSICAL CONSTANTS OF HYDROCARBONS
"Note 12. The 'first free angle* is the first angle, not also part of another ring,
from which one may proceed clockwise around the ring.
"Note 13, The 'upper right ring* is the highest ring in the formula or, if
two or more are equally high, then the ring farthest to the right in the highest row.
"Note 14. Ordinarily, no numbers are needed for carbon atoms that are
common to two or more rings. When such a need does arise, it is recommended
that they be numbered by adding a (or 6, c, etc., in case of a succession of them)
to the number of the position just preceding in the clockwise order; interior carbon
atoms are considered to follow the highest number."
Examples:
XXXV
XXXVI
Author's note: In numbering the alicyclic series, the system is not changed entirely but is
slightly different for saturated fused ring systems than that generally accepted for aromatic
hydrocarbons, For example: Naphthalene is numbered thus:
while the decahydronaphthalene, [0,4,4]-bicyclodecane is numbered thus:
This method is in line with that in general usage for the fused rings of the following type:
"C. THE SYSTEM DOES NOT BELONG TO CLASSES A AND B, AND DOES NOT
CONTAIN FREE SPIRO UNIONS
"I. The system consists of two rings only, separated by either an atomic bridge
or a valence bridge.
"Note 16. Formulas of systems belonging to Class C, I must be drawn so that
the bridge contains as few members as possible.
INTRODUCTION
Examples:
H 2 C
CH
XXXVII (right)
CH
XXXVIII (wrong)
"Rule 13. Starting with one end of the bridge as 1, number around the longe;
way to the other end of the bridge, then on around the shorter way to the beginning
and finally* by the shortest path, along the bridge itself if the bridge is atomic. I
there are two or more possibilities for the shortest path, choose the shortest patl
from the* highest previous number that will give a decision. Number all rinj
members.
Examples:
CH
CH
XL
"II. The system contains one or more atomic bridges the removal of whicl
would throw the system into Class B.
"Rule 17. Disregarding the atomic bridges and converting the resulting forn
to the lowest stage of hydrogenation, number by Rules 6, 7, 10, 11 and 12; thei
number the bridge members, following the shortest path as in Rule 13.
Examples:
XLIII
XLIV
"Note 17. The atomic bridges in Class C, II must contain as few members ai
possible.
"III. The system does not belong under I or II.
"Note 18. The systems of Class C, III contain two or more bridges, eithe
atomic or valence. Special care must be taken to draw the formula so that th<
bridges shall be as simple and of as few members as possible. A branched bridg<
is regarded as consisting of a main bridge and one or more branch bridges, ^
branched bridge should be preferred to crossed bridges even though it contain
more members (see XLVII and XLVIII), but in no case should the chain o
28
PHYSICAL CONSTANTS OF HYDROCARBONS
bridge members between the two bridge ends be greater than either of the outside
chains between the same points. In difficult cases it may be advisable to construct
a spatial model so as to decide upon the most natural plane formula.
H 2 C
CH
CH
H 2 C
HC
HC
CH
CH 2
XLVII
CH
XLVIII
"Rule 18. Select as the chief bridge (one end of which becomes Position I)
the one having the most members or, if two have an equally large number of
members, the one that divides the outside ring more symmetrically; number as in
Rule, 13; then number any remaining bridge members by the shortest path.
Examples: See XLV, XLVI, XLVII.
"Rule 19. Of two or more numberings conforming to Rule 18, choose the one
that gives the lowest numbers to the ends of the other bridges.
Example:
H 2 C
"D. THE SYSTEM CONTAINS ONE OR MORE FREE SPIRO UNIONS
I. The system contains spiro unions only.
"Rule 21. Beginning with a ring member next to the spiro atom in the right
end ring, number clockwise around the end ring and on around the entire formula.
Number all ring members.
Example:
CHj
CH 2
H a C<6
2>CH 2
"Rule 22. Of two or more numberings conforming to Rule 21, choose the one
that gives the lowest numbers to spiro atoms."
INTRODUCTION
29
Examples:
CH 2
H 2 C(7
3>CH 2
CH 2 CH 2 CH 2
Wrong
Author's note; The placing of the double bond has been changed to the one position in this
study rather than the six position as is shown in the following. See Chemical Abstracts:
CH
2>CH 2
Wrong
CH 2 CH 2
Right
C. Definition of Bi and Di in Alicyclic Nomenclature
In the nomenclature herein adopted for the alicyclic hydrocarbons it has been
necessary to differentiate the fused (shared) or "endocyclic" from the "exocyclic"
ring structures. The distinction between these two systems has been accomplished
by arbitrarily using the prefix bi for hydrocarbons of fused rings or endocyclic type,
and the prefix di for the separated rings or exocyclic type as illustrated in the
examples:
[0,2,2]-Bicyclohexane
Dicyclohexyl
The prefix di is also used to denote two separate rings joined to the same carbon
atom as illustrated in dicyclohexylmethane
and di is also used as in dicyclohexylylmethane
o-o
In the present study the latter two cases are distinguished by the suffix -yl in the
case in which the two rings are joined to each other directly.
30 PHYSICAL CONSTANTS OF HYDROCARBONS
In order to name the bicyclic compounds a unique system of numbering in
relation to the rest of the compounds had to be adopted. For such compounds as
the following
there was no method in existence which properly accounted for the fused ring
state of the molecule. The system in use at present was proposed by Baeyer and
the following conventions adopted: in the preceding formula the method of
naming is as follows [l,2,2]-bicycloheptane. The first number considered is the
number of carbons on the bridge, the next two numbers denote the number of
carbons pn either side of the bridge ; the first (according to our own method) denotes
the number of carbons to the right of the bridge and the second, the number to the
left.
The foregoing usage of the prefixes bi and di will be followed consistently in
this study.
D. Supplementary Nomenclature Considerations
The foregoing Geneva nomenclature rules are not sufficiently extensive to
cover some complex polycyclic compounds and therefore will be supplemented by
nomenclature taken from Beilstein 14 based upon the work of Baeyer, Stelzner, and
Kuh.
The generalizations relating to the 2 and 3 ring, fused and condensed ring
systems are given :
"1. Polycyclic hydrocarbons with an indirect linkage of single rings.
"The systematic naming of these hydrocarbons and derivatives is more easily
accomplished if the following combinations are named with reference to the straight-
chain hydrocarbons present in the compound.
\
Examples:
CeHii . CH 8 . C e Hn Dicyclohexylmethane
C 6 Hn . CH . C 6 Hn Tricyclohexylmethane
I
CeHu
. CH 8 . CH* . C 6 H U 1,2-Dicyclohexylethane
Cyclopentylidenecyclohexylmethane
"Proceeding with the aforementioned names to designate the homologues,
substitution products, etc., the following numbering system is proposed.
(14) Beilstein, Vol. V, pp. 8-14, 1922
INTRODUCTION
31
Examples:
/y
"2. Polycyclic hydrocarbons with directly connected ring structures. A
general designation of this type of compound might be 'diphenyloid' since the
original structure of this type was diphenyl.
"A method adopted for the naming of individual representatives of the double
ring system is the use of one hydrocarbon ring as a stem and the other as the sub-
stituent.
Examples:
Cy clopropy Icy cloh exane
1 ,2-Dicyclohexylcyclopentane
"The following rule is applied for both aromatic and alicyclic structures. The
handling of the double nuclear symmetrical ring system allows two methods of
naming, either as a double radical or according to the method previously shown.
The literature contains both dicyclohexyl and bicyclohexyl for the following
formula:"
Dicyclohexyl, bicyclohexyl, or cyclohexyl-cyclohexane
32
PHYSICAL CONSTANTS OF HYDROCARBONS
Author's note: In our study of formulae of this type, the term dicyclic has been used to dif-
ferentiate these hydrocarbons from those with internal rings,
Beilstein states that: "The numbering is shown as follows:
The nomenclature of diphenyl and its homologues and unsymmetrical derivatives
is based on diphenyl, as for example, 4,4'-dimethyldiphenyl, or as another example
of nomenclature for the same compound, ,'-ditolyl.
"For naming a univalent and a bivalent radical the diphenyl radicals are shown
as follows:
CH B . CeH 4 -Diphenylyl or xenyl
C ft H 4 . CeH 4 Diphenylene
"Where the formulae are employed without the positions being designated,
the diphenylyl radical is understood with the one free valence at the 4 position or
para to the connecting bond. The diphenylene structure has the valence at the
2 and 2' or the ortho positions.
C. Polycyclic Hydrocarbons with Internal Rings
"Polynuclear ring systems that are of known structure contain fixed structures
within the single ring. These are considered as condensed rings. The polynuclear
ring systems characterized by having more than one ring in their fixed ring struc-
ture are considered as two rings fused together.
"One considers as condensed rings, polynuclear ring systems which are character-
ized by having more than one ring in their fixed ring structure. The single rings
are, to a certain degree, fused together. Ring condensation of two single-rings
present the following possibilities:
1. One carbon atom is common to both rings. The spiro configuration is the
case where one carbon is shared by both rings.
2. Two adjacent carbons are common to both rings.
INTRODUCTION
3. There are more than two carbon atoms common to both rings.
33
"Condensed ring systems which can be split into more than two single rings,
can come about if the above manner of condensation is repeated so that no one
ring member is common to more than two single rings.
4. Certain carbon atoms are common to more than two single rings.
"For the derivation of systematic names in these different classes of condensed
systems there are no fundamental rules carried over into general use which are
extensively applicable. The attempts which have been made in this direction
and which have yielded good results for certain parts show that the problem is
most difficult and that there is small chance of reaching a solution which combines
clarity of nomenclature with satisfactory simplicity. Thus is justified the historic
procedure which has been developed and by which each polynuclear system whose
significance extends through a number of known derivatives, is covered with a
characteristic name. Nevertheless the necessity for the systematic or 'half sys-
tematic* nomenclature of the few polynuclear rings worked on remains persistent.
This was shown especially in the years during which the literature search for this
handbook (Beilstein) was carried on and in the different attempts at completion of
preliminary principles and their extension. In a comprehensive way (1922) during
a similar consideration of isocyclic and heterocyclic compounds, Stelzner and Kuh
in the introduction to Vol. Ill of 'Literatur-Register der Organischen Chemie'
attained the object for the basis of this book (Beilstein). Since this work is closely
correlated with our book, the naming of compounds obtained according to the
suggestion of Stelzner and Kuh, were, in suitable cases, used beside that in the
original literature or according to established custom and are quoted with struc-
tural names. The following explanations are limited essentially to the prevailing
practice of 1910.
34
PHYSICAL CONSTANTS OF HYDROCARBONS
"A proposal of Baeyer frequently followed in the literature can be applied to
the bicyclic systems of cases 2 and 3. It suggests that one unite in the name, the
total number of carbon atoms in the ring with the prefix bicyclo; this specifies by
means of figures how many carbon atoms on each of the bridges lie between the two
tertiary carbon atoms found at the place of ring branching. Thus one arrives at
the name bicyclo-[l,2,2]-heptane for the hydrocarbon shown in the formula.
The numbering begins at a tertiary carbon turning the ring branching first in the
wider then in the narrower orbit and going over finally to the carbon atom of the
shortest bridge. Accordingly, the unsaturated hydrocarbon of formula
may be designated as bicyclo-[0,4,3]-nonatriene-l(6),2,4."
Up to the present time (August 1939) there has been no systematic method
entirely satisfactory for naming the tricyclic groupings both of endo and exocyclic
types of hydrocarbons. However, it is possible to apply in a limited way, the
methods from bicyclic nomenclature to the naming of the triendocyclic compounds,
as for example:
c
1 ,4-Endoraethylene-[0, 1 ,3] 8 > 6 -bicyclohexane
The common name for such a configuration is apocyclene or tricyclene, which is,
as usual, unconnected with the structure. The superscripts shown in the formula
for bicyclo compounds, as (0,4,4) M both in the unquoted part of the intrqduction
and in the section on bicyclanes and bicyclenes are used to denote the positions at
which the fusion of the inner bond is located.
The other tricyclic groupings have been difficult to designate in a systematic
manner and therefore have retained their common name, for example :
Perhydroanthracene, or as a Geneva system name:
bicydodecane.
2,3-Cyclohexano-[0,4,4]- M
INTRODUCTION 35
The method of naming exocyclic tricyclo compounds is to use the prefix tricyclo
with the suffix denoting the number of carbon atoms in the individual ring. This
leaves no method for differentiating the endotricyclic compounds by use of a dif-
ferent prefix meaning three as in the relation of bi and di as adopted in this study.
For compounds of higher ring structure, the application of the Geneva system
would be too cumbersome and tend toward ambiguity, although the hydrocarbons
can be named as shown in the preceding examples.
The common names of the hydrocarbons have been included with the systematic
ones, and an index for all of the common names will appear in the fourth volume of
this work.
4. Critical Evaluation of ' the Data and Calculation of the Most Probable Values
A. INTRODUCTION
The problem of critically evaluating the experimental data has been somewhat
complicated by investigators who have not reported probable errors of their
physical constants; nor have they given sufficient details of their experiments to
enable one to evaluate their constants with the degree of accuracy comparable to
Volume I on aliphatic hydrocarbons. Since there is no one method by which the
probable errors can be calculated from the alicyclic constants, an estimate has
been made of the probable degree of reliability by consideration of the mode of
synthesis, purification, and measurements.
In general, the physical constants of members of the alicyclic series are less
reliable than those of the aliphatic series. The specific gravities and indices of
refraction of aliphatic hydrocarbons are, on the average, reliable to one or two
parts in 10,000; in contrast, the alicyclic variations are from two to four parts in
1,000. A striking example of inconsistency in the data is found in the data for
1-methylcyclohexene-l. There are data attributed to this compound which agree
more closely with the more reliable physical constants of 3- and 4-methylcyclo-
hexene-1. The experimenters have probably overlooked the possibility of iso-
merization of the compound during identification and measurement of the con-
stants. This type of error may occur frequently but cannot be detected in this
study because of a scarcity of accurate data for the pure compounds.
A discussion of the methods used in evaluating the melting points, boiling
points, specific gravities, and refraction indices are given as follows :
B. MELTING POINTS
There are fewer data for the melting points of alicyclic hydrocarbons than for
any of the other physical constants collected. Less than twenty per cent of the
compounds have melting point data. A critical analysis of the data is impractical
at this time because in most cases only one or two values are given for any one
compound.
C. BOILING POINTS
For each hydrocarbon the boiling point data are listed in order of decreasing
pressure. The pressure in millimeters corresponding to each boiling point is given
36 PHYSICAL CONSTANTS OF HYDROCARBONS
unless this pressure is 760 mm. in which case it is omitted. The value given in
bold-face type for each hydrocarbon is a weighted average of the experimental
values given at 760 mm.
There are more values for specific gravity of the alicydic hydrocarbons than
for either the melting point or boiling point values. The specific gravity may be
determined more accurately than either the melting or the boiling point.
D. SPECIFIC GRAVITY
In determining the temperature coefficients of specific gravity, it is assumed
that the variation of specific gravity with temperature may be expressed by the
equation:
Di-DH>+a(t-t Q ) + b(t-t )*, (1)
in which Dl is the specific gravity of the substance at the temperature t, Dl Q the
specific gravity at some constant temperature to, and a and 6 are constants to be
evaluated.
The constants D{ (* usually being 20), a, and b were determined by the
method of least squares. If the data are for the same temperature, the method of
least squares is equivalent to taking the weighted average of these data.
The temperature coefficient of specific gravity, i.e., the derivative of D\ with
respect to t, obtained from equation (1) is
- (2)
(3)
In all but a few cases equation (1) represents a degree of accuracy unjustified
by the experimental data. Under these circumstances equation (1) degenerates
into
t*) (4)
and equation (3) to
dD /e v
ar fl < 5 >
Equation (4) reproduces the data to within three or four units in the third decimal
place or about one part in 200.
The adopted value of D' is given in the specific gravity column in bold-face
type, the last figure of which is usually given in small type, e.g., 0.0812 2 . This
signifies that the last figure is to be used only in calculating specific gravities at
temperatures other than 20, Equation (3) or (5) is given in the additional data
column.
When values in the form D%{ are reported, t\ being different from 4, the values
of Dfr are calculated by means of the formula
D? (hydrocarbon) - D\\ (hydrocarbon) X JDi 1 (water).
INTRODUCTION 37
D\\ is numerically equal to the density at fe in c.g.s. units when t\ refers to the
density of water at 4.
The specific gravity values for each compound are listed in order of decreasing
temperature. When the specific gravity was determined at 20, this temperature
was not recorded since the heading is given as >5. If the specific gravity is
referred to water at a temperature other than 4, this fact is indicated by D% follow-
ing the specific gravity value (h and fe being expressed numerically).
, E. INDEX OF REFRACTION
For each compound the indices of refraction are given for the H, Hp, H 7 ,
Naz>, He r , He v , and He, lines wherever data permit. The subscripts r, y, and g
on the He lines signify red, yellow, and green respectively. The temperature of
the index of refraction measurement is indicated by a superscript on the symbol
designating the line. Thus 1.42S6S, n^ signifies that the value of the index of
refraction at 20 C. for the H line is 1.42565.
The wave lengths of the above-mentioned lines are given below.
TABLE I Wave Lengths of the Principal Lines Used in Index of Refraction Measurements
Line Wave Length, A
He, 6678
Ha 6563
NaD 5893
He,, 5876
He* 5016
Hp 4861
H r 4341
The temperature coefficients of the index of refraction are evaluated by the
same method used for specific gravity. The changes with temperature are smaller
but of the same order of magnitude as those of specific gravity. The value of
WD (/o =* 20 whenever possible) is given in the index of refraction column in bold-
face type, and that of the temperature coefficient in the additional data column.
The values of the indices of refraction are referred to the sodium D line unless
otherwise indicated and are tabulated in a manner similar to those for specific
gravity.
5. Description of the Tables
A. STRUCTURAL FORMULAE
In writing the structure of the carbon skeleton of an alicyclic hydrocarbon,
attempts are generally made to show only the number of carbon atoms in the ring.
There is no intention to imply literal geometrical relation in the drawings. As a
38
PHYSICAL CONSTANTS OF HYDROCARBONS
result, a lack of uniformity occurs in writing the carbon skeletons of ring compounds.
For example, cyclopentane is shown in a recent textbook of organic chemistry as
follows :
H 2 c
H 2 C
c-c-c-c-c
In the present work an attempt is made to depict the carbon rings so as to
correspond as closely as possible to the configuration of the carbon nuclei as dis-
cussed in an earlier section.
For each hydrocarbon, only those carbon atoms not part of a ring are explicitly
written, except for shared rings as noted later. The monocyclic rings from cyclo-
propane to cyclooctane inclusive are simply depicted as regular polygons. Thus,
cyclobutane, methylcyclopentane, and 1,2-dimethylcyclohexane are written as
follows:
0-Xylene is often written in the same way as 1,2-dimethylcyclohexane above.
However, this should result in no confusion to the reader inasmuch as compounds
containing aromatic rings are not reported in the present volume, In volume III
the aromatic rings will be distinguished from the alicyclics by the use of double
bonds corresponding to any one of the Kekule-type structures.
Aliphatic side chains containing five or more carbon atoms in a straight chain
will usually be written in an abbreviated manner. Thus, heptylcyclopentane will
be written as
C-(C) 5 -C
c-c-c-c-c-c-c
instead of
If the aliphatic side chains on the rings are normal, i.e., unbranched, the letter
n has been omitted before the name. Thus butylcyclopentane will signify w-butyl
cyclopentane.
As has been explained, the structures of many ring compounds, particularly
those containing shared rings, are not known with certainty. As a consequence,
the structural formulae have been reported more than one way in the literature
INTRODUCTION
39
even when the attempt is made to show the geometrical configuration; i.e., [0,2,2]-
bicyclohexane is shown as either
or
Although it is more frequently found in the literature in the former way, we shall
write it in the latter way (i.e., as two squares) because it has been shown in a previ-
ous section that this is somewhat nearer the actual configuration.
[0,l,3]-Bicyclohexan'e will be written in the form usually found in the literature,
i.e., as
even though it would be more correct to write it as
The
latter is never given and might result in some confusion if it were adopted here.
In shared rings having three or more carbon atoms in common, all the shared
carbon atoms except the terminal ones will be written explicitly. Thus, [1,2,2]-
bicycloheptane and [2,2,2]-bicyclooctane will be written as
and as
I | respectively.
In polycyclic compounds containing more than two shared rings, the foregoing
conventions are not strictly adhered to.
B. INTRODUCTION TO TABLES
The tables contain the experimental data on melting point, boiling point, specific
gravity, and index of refraction. The bold-face figures are weighted statistical
averages of all the values collated to March, 1939.
II. CYCLANES OR CYCLOPARAFPINS
1 . Cyclones with alkyl substitutions CH$ n
2. Cyclanes with an alkenyl or olefin substitution djitn-i
3. Cyclanes with two alkenyl or olefin substitutions CH 8 _
4. Cyclanes with an alkadienyl or diolefin substitution
5. Cyclanes with an alkynyl or acetylene substitution CnHin^
6. Cyclanes with a cycloalkenyl or cyclo6lefin substitution C n H Sn _4
7. Cyclanes with a bicyclenyl or bicyclodlefin substitution CHm-
C,H, 42
1. CYCLANES WITH AN ALKYL OR PARAFFIN SUBSTITUTION
Name and Carbon Skeleton
Jlf. P.,C.
B. P., C.
@ 760mm
^5
-s
Additional Data
Cyclopropane
-126.9
-33
0.688,
@-40
1.377,
^= -0.001 16/C.
(-80 to -35)
A
- 127 *
-126 24 *
-32.6 to
-33.6 14
-32.89"
0.6807 8
-32.75
1.3726 7
@
-32.75
^ (-80 to -35)
-32.9
0.6886 8
1.3769 7
- 32.89 >
@ -40
@ -40
@ 755.9mm
0.720 24
1.3799
-34.5 24
@ -79
@-42.5
@ 750mm
0.7352
1.3790 20
@ -80
@-42.8
1.3898 20
@-60.0
1.3971 20
@-7l.2
1. 4024 7
C<H,
Methylcyclopropane
c
4to5 6
0.6760
1
-8
A
0.691 2 B
43
Name and Carbon Skekton
Af. P.,C.
B. P., C.
@ 760mm
Of
ng
Additional Data
Ethylcyclopropane
34.5
0.677,
1.379
^=-ooooioorc
c c
i
35.75 '
0.6784 *!>
1.3789
dt (0 to 20)
A
@ 765mm
36 to 36.5 M
34.5 to 35 <- 2 < b
0.6764 lfl
0.6832 23
0.6866
1.3791 23
1. 37973"
1.3780">
36.5 to 37
@ 18.25
@ 755mm
0.6975 4 - 2<B
0.7055 22
1,1-Dimethyl-
cyclopropane
c c
21 9,io
0.6604 "
1.3659^0
Y
0.6619 '
1.36869*
A
@17
@17
44
Name and Carbon Skeleton
M. P.,C
B. P., C.
760mm
Of
s
Additional Data
1,2-Dimethyl-
cyclopropane
low boiling
32.4 to 33.2 a
0.6754 a
1.37129*
C
\
C
@ 761mm
28.8 to 29*
@ 758.9mm
0.6769*
1.38023*
1.38702 s
1.39109 s
w 20
high boiling
37.2 to 37.4*
0.6928 2
1.38223 s
@ 755.5mm
0.6985 *
1.3694 1 2
M 20
*.
0.71325*
1.37617 s
1. 37997 2
T
1. 37493
1.38209"
1.38598 * l
y
(Probably cu-ttans mixture)
32 to 33
0.6806
1.3763
0.7025 M
1.3774
@0
@18
1.3787 s *
@16
1.3798* 8
U813*
1.3823
@10
45
Name and Carbon Skeleton
M. P.,C.
B. P., e C.
@ 760mm
Pf
t30
Additional Data
Propylcyclopropaiie
c-c-c
68.5
0.7121 *
1.39S7
1
@ 16.7
(3i 18
A
1.3963*
16.7
1-MethyM-ethyl-
cyclopropane
c
1
64.9 to
0.6961 17 - 18
1.3876 "
A
65.9
63.9 to
64.9 .
21
0.6959 jy
0.6960 "
21
1.3874"
21
N^
C-C
1.3874 "
1.3880 17
1,1,2-Trimethyl-
57
0.681 4
1.386,
cyclopropane
c c
\y
59 to 60
@ 768mm
0.6949 "
1.3866 1 *
1.3848
/\
59 to 60
0.6822 s
@ 19.5
L A
52.8
19.5
1.3896"
c
756mm
0.6888 4 - Jl
14.5
52.5"
15.3
1.38738"
752mm
n%*
56 to 57"
1.39505"
@ 750mm
n x'*
1. 39975 ll
W 14.S
*T
46
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
DT
*s
Additional Data
1,2,3-Trimethyl-
cyclopropane
c
A
X \
c c
65 to 67 2
@ 755mm
0.6946 M
1.3945 M
l-Methyl-2-propyl-
cyclopropane
c
i
92 to 93 17 -"
0.7206 n - ie
1.4003 17 ' 19
A V
oc-c
l-Methyl-2-isopropyl-
cyclopropane
c
\
c-c
1
81 I3
@ 748mm
0.7102 13
1.3927"
1
c
47
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
iff
8
Additional Data
l-Methyl-2-(2-mejthyl-
propyl) cyclopropane
c
i
109.5 to
0.7403 13 - 26a
1.4088 13 - 26 *
A
110.513.25*
\
c-c-c
1
c
i-Methyl-l,2-diethyl-
cyclopropane
c-c c
108 to 109 25a
0.7381 26a
1.4102 26 *
V
A
\
C-C
l,l,2-Trimethyl-2-
ethylcyclopropane
c c
\/
103.5 to
104.5 17
0.7418 "
@ 20.4
1.4129 17
@ 20.4
c-c
48
Name and Carbon Skeleton
\f n o/"
JxL, Jr, 9 C.
B. P., C.
@ 760mm
D?
8
Additional Data
l,l-Dimethyl-2-
(2-methylpropyl)-
cyclopropane
c c
125 to 126"
0.7 187
1.4032"
V
&
0.7347
v
D\
c~c-c
1
1
c
(1) A. Ashdown, L. Harris, and R. T. Armstrong, J. Am. Chem. Soc. 58, 850, 1936.
(2) J. Baudrenghien, Bull. soc. chim. Belg. 38, 172, 1929.
(3) J, Boeseken and H. V. Takes, Rec. trav. chim. 56, 858, 1937.
(4) G. Chavanne, Bull. soc. chim. Belg. 31, 338, 1922.
(5) N. Demjanoff, Ber. 28, 23, 1895.
(6) A. V. Grosse, J. Am. Chem. Soc. 59, 2739, 1937.
(7) A, V. Grosse and C. Linn, Unpublished data.
(8) A. V. Grosse and R. Wackher, Unpublished data.
(9) G. Gustavson, J. prakt. Chem. [2] 62, 271, 1900.
(10) G. Gustavson and 0. Popper, J. prakt. Chem. [2] 58, 458, 1898.
(11) H. B. Mass, E. T. McBee, G. E. Hinds, and E. W. Gluesenkamp, Ind. Eng. Chem. 28, 1178,
1936.
(12) N. Kishner, J. Russ. Phys. Chem. Soc. 44, 169, 1912.
(13) N. Kishner, J. Russ. Phys. Chem. Soc. 45, 957, 1913.
(14) K. W. P. Kohlrausch and P. K6ppl, Z. physik. Chem. B26, 209, 1934.
(16) R. Lespieau, Bull. soc. chim. [4] 47, 847, 1930.
(17) R. Lespieau and R. L. Wakeman, Bull. soc. chim. 51, 384, 1932.
(18) R. Lespieau and R. L. Wakeman, Compt. rend, 192, 1395, 1931.
(19) R. Lespieau and R. L. Wakeman, Compt. rend. 192, 1572, 1931.
(20) C. Linn, Unpublished data.
(21) G. J. Ostling, J. Chem. Soc, 101, 457, 1912.
(22) 0. Philipow, J. prakt. Chem. [2] 93, 162, 1916.
(23) N. Rosanow, J. Russ. Phys. Chem. Soc. 48, 168, 1916.
(24) M. Trautz and W. Winkler, J. prakt. Chem. [2] 104, 37, 1922.
(24a) R. Wfflstatter and J. Bruce, Ber. 40, 3982, 1907.
(24b) N. D. Zelinsky and B. Schtscherbak, J. Russ. Phys. Chem. Soc. 44, 275, 1880, 1912; Ber. 46,
169, 172, 1913.
(25) N. D. Zelinsky and M. N. Ujedinoff, J. prakt. Chem. [2] 84, 543, 1911.
(25a) N. D. Zelinsky and A. Upensky, J. Russ. Phys. Chem. Soc. 45, 831, 1913.
(26) N. D. Zelinsky and J. Zelikow, Ber. 34, 2856, 1901.
49
C,H,
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
DT
Additional Data
Cyclobutane
/\
-80"
11 to 12 >
0.7038 "
1.37520
\/
0.7185 l6
@ -5
Methylcyclobutane
38,6
0.6931
1.3837
dD
dt (0 to 20)
c
39 to 42 ^
0.6931 3
1.3780 19
i
dn
1
36.3*
0.6784 19
1.3836*
34 to 35 1J >
0.6950 3 - 13
1.3850 4
(15 to 20)
36 to 36.5 13
@ 18
1.38463
@ 755mm
0.6976 3
18
35 to 36 3
@15
1.38473 13
@ 753mm
0.7118 13
@ 18
@o
1.386
0.7120*
@ 15
@0
0.7135 3
@0
0.6975 19
Ethylcyclobutane
71.5
0,7450
1.402
~-0.00090/C.
c c
- 143.2 "
72.2 to
0.7450 7
1.4004*
d< (10 to 20)
1
72.5
0.7284
1.4023 u
70.7
Dl*
1.4080
70
0.754017
@ 19.5
@ 754mm
@10
1.4032
0.7461
@ 15
rf
50
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
^
B
Additional Data
1,2-Dimethyl-
cyclobutane
c
68 to 70 20
0.7122
1.3988*
6-
@ 740mm
Propylcyclobutane
c-c-c
99 to 100 "
0.7440
1.41 19 18
1
@ 736.2mm
@19
@19
Isopropylcyclobutane
c-c-c
90.5 to 91.5 s
0.7464 *
1.4096 1
1
@ 750mm
@ 14.5
@19
1.4125
@ 14.5
51
CgHit
Name and Carbon Skeleton
M. P.C.
B. P., C.
@ 760mm
Iff
8
Additional Data
3-Cyclobutylpentane
c-c-c-c-c
1
151 to 152 7
0.7945 7
1.4334 7
O
1,2-Diisopropyl-
cyclobutane
c c c
1
157 to 158.5 9
0.7755 9
0.7901
1.42787"
1.42565'
T
1.43316'
H H
1. 43755 s
V
l,l,2-Trimethyl-3-
isopropylcyclobutane
c c
V
145 to 146.5
0.7598 9
0.7744 9
1.41997*
1.41781*
n *H
1
c-c-c
1.42527*
1.42980*
T
52
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Df
-8
Additional Data
l,2-Dimethyl-3,4-
diethylcyclobutane
c
1
155 to 156
0.7729 "
1.42447"
1.42193"
c
W^O
1
c c
1.42950"
w ^
1. 43377 ll
1,1,3 ,3-Tetramethyl-
2 ,4-diethy Icy clobutane
c c
\/
/\
124 to 125 16
c-c <^ \~c-c
X\
c c
CM HZS
1,1,2,2-Tetramethyl-
3,4-diisopropylcyclo-
butane
c c
106 to 107 12
0.8035 J2
1. 44580 12
\y
@ 27mm
@ 17
@ 17
<^\S
0.8181 12
I \ / \
i \^ r*
@o
c-c-c
53
(1) G. Chavanne, Bull. soc. chim. Belg. 31, 331, 1922.
(2) H. G. Colman and W. H. Perkin, J. Chem. Soc. 53, 185, 1888.
(3) N. Demjanoff and M. Dojarenko, J. Russ. Phys. Chem. Soc. 45, 176, 1913.
(4) A. V. Grosse and- V. N. Ipateiff, J. Org. Chem. 2, 447, 1937.
(5) B. A. Kasansky, Ber. 69, 950, 193d.
(6) N. Kishner, J. Russ. Phys. Chem. Soc. 45, 973, 1913.
(7) N. Kishner and Amasow, J. Russ. Phys. Chem. Soc. 37, 518, 1905.
(9) S. Lebedev, J. Russ. Phys. Chem. Soc. 43, 820, 1911.
(11) S. Lebedev and L. Mereshkowsky, J. Russ. Phys. Chem. Soc. 45, 1348, 1913.
(12) L. Mereshkowsky, J. Russ. Phys. Chem. Soo. 45, 1925, 1913.
(13) O. Philipow, J. prakt. Chem. [2j 93, 162, 1916.
(14) J. Smittenberg, H. Hoog, and R. A. Henkes, J. Am. Chem. Soc. 60, 17, 1938.
(15) E. Wedekjnd and M. Miller, Ber. 44, 3285, 1911.
(16) R. Willstatter and J. Bruce, Ber. 40, 3982, 1907.
(17) N. D. Zelinsky and J. Gutt, Ber. 41, 2431, 1908.
(18) N. D. Zelinsky and B. A. Kasansky, Ber. 60, 1101, 1927.
(19) N. D. Zelinsky and B. Schtscherbak, J. Russ. Phys. Chem. Soc. 44, 1880, 1912.
(20) N. D. Zelinsky and M. B. Turova-Pollak, J. Gen. Chem. (U.S.S.R.) 2, 666, 1932.
54
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
/>r
5
Additional Data
Cyclopentane
-94.4
49.3s
0.7460
1.4068,
^~0000949/C
O
-94.1 34
-.94,368
-94.8 4
49.5
767mm
48.4 to 48.6 81
@ 763mm
0.73572 >
@30
0.7506 M
@20.5
1.4057 73
25.5
1.4061 62
21.8
** ' (0 to 30)
^~ -0.000484/C.
d (10 to 25)
50.25 to
0.7543 21
1.4039 64
50.75 fl4
20.1
@20.5
49.5 lo
0.7447 84
1.4060 31
49.4 to
0.7457 19 - 26
1.4065"
49.5 19 - 26
0.7471
1.40672 6l
49.37 "
0.7510 18
1.4070 ""
49.35 to
0.7531 31
1.4075 64
49.40 4
0.7491
1. 40910
49.35 > 2
@17.5
@15
49.30 M
0.7494
1.4094 4
49.2 "
17.1
@15
49 to 51 73
0.7490 72
1.4101 72
49.0 20
@15
@15
49 28,29,30
48.5 3l
50.0
@ 756mm
48.5 to 51
@ 748mm
0.7498 19 - 26
@15
0.750 10
0.7503
0.75033 M
1.4101 52
14.7
1.4100"
13.5
1.4321 52
@-26.8
1.40464 21
0.7505 4
9720.1
""a
1.40464"
0.7500 23
14.7
0.754
,,20.0
H a
1.40383 18
W 20
14.7
1.40702 60
0.7502
n u
0.7517 J0
1.4074 4
12.7
0.7645 4
1.40770"
0.7646 12
1.41 173 21
@o
n *H l
0.76498 w
@0
1.41166"
n%-
55
Name and Carbon Skeleton
\r n o/i
M. r. t C.
B. P., C.
760mm
tf
"3
Additional Data
Cyclopentane
(Continued)
1.41 126 "
n
1.41417 60
1.4145
1.41481 23
**I4.7
1.41589 21
y
1.41520"
7,20.0
n u
y
1.41536 18
7
1.4185 4
^
1.41891
7
1. 40609 18
1.40981 28
1.41318 M
*a
1. 40668 "
1.41 723 60
*
1. 40927 M
56
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
/?;
Additional Data
Methylcyclopentane
- 142.2
71.9 4
0.7488,
1.4099 6
^=-0000916/C
c
-1414,7
72 to
0.7293
1.4088 w
rf/ (0to40)
A
- 141.9 3
72.2 7 . 8 -"
@41.2
@21
^= S _0000475/C
o
- 142.4 6
72.00 fl
0.7303 "
1.4098 33
dt (10 to 20)
\ /
-142.7 6
72 io
@40.2
1.4099 19 - 26
- 143.0 6
719 4,12,19,26,68
0.73948
1.40998"
71.8 to 72 ^
@30
1.4100 68 - 80
71.8 33
0.7474
1.4096 77
7 1.5 to 72.5 26
@21
@ 19.5
71 to 72.5 71
0.7459 18
1.4104"
71 to 72 80
0.7487 33
@18
70 to 72.5 4
0.7496 19 ' 26
1.41 19 71 - 73
70 to 71 24 - 47
0.7510"
@15.5
71 to 72 4
0.7508
1.41237 o
@ 755mm
D
@ 15
70.0 to 70.5 18
0.7488 77
1.4126 4
@ 755mm
@ 19.5
@ 15
71 to 72 38
0.7515 "
1.4111 28
@ 752mm
@ 19.5
@ 13.5
70.9 to 7 1.0"
0.7473 5
1.40788"
@ 751mm
@ 18
n /f' a
71 to 72.5 73
0.7505 73
1.40750 18
@> 745mm
@ 15.5
n' 20
71 n
0.7505 71
a
@ 743mm
15
1.41023 60
71. 5 to 72 4
0.7528 4 ' 12
^a
@ 742mm
15
1.4104 4
7 1.5 to 72.5 fl6
0.753 10
""a
@ 740mm
@15
1.41511"
0.7530 4
W 20.0
@> 15
"a
0.7533 10
1. 41465 18
0.75343
1.4176 4
0.7541 19 - 2B
1.41 760
0.7562 "
H H
@ 14.8
1.41824"
0.7511 28
n '
Dia',1
1.41868 l8
0.7666 4 - 12
n 20
,
7
57
Name and Carbon Skeleton
TLJf 7> OS*
M. Jr., C.
B. P., C.
@ 760mm
Iff
<
Additional Data
Methylcyclopentane
(Continued)
0.76737 60
1.4214*
@0
7
0.76615 <
1.40947 18
0.76641 4fl
1.41649 60
0.76829
^S
1. 40975 60
r
1. 42064 M
1.41254"
*,
C,Hu
58
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D?
-B.
Additional Data
Ethylcyclopentane
103.4
0.7657
1.4197.
dD - 0000932/C
oc
- 137.9 7
103.6 61
0.7478
1.4190"
d/ (15 to 40)
6
103 to 103.5
103 to 103.2 7
103.0 19 .* B
@40
0.7610
0.7632 "
@21.8
1.4196 61
1.4201 19 ' 26
- -0.000496/C.
^ (5 to 25)
103 "
0.7642
1.4202 71 - 78
100.5 to
0.7654
1.4201 7
101.5 71
0.7695
@ 19.1
100.5 to
0.7669
1.4188 M
101.0"
@ 19.9
@ 18
@ 756mm
0.7658
1.4222 "
100.5 to
@18
@ 14.7
101.5 7I
0.7736 .
1.4269
@ 740mm
@15
@5.8
0.7711 7
1.4425"
@ 14.9
@-26.7
1.41612 18
1.4179 7
M 18.85
1.42332 18
1.4253 7
1.42798 18
n a
1.41840 u
S.
59
Name and Carbon Skeleton
U. P.,C.
T T> O/*
.0. -r., C.
@ 760mm
DT
^
Additional Data
1,1-Dimethyi-
0.7523
1.4126
cyclopentane
c c
-76.4 2
88 40
0.7509 *
1.4122 s
v
o
-.779
@ 762mm
87.5 *'
86.5 to 87.4 '
0.7551
0.7546 40
n 20
X/o
1.4131 40
1.4136 MO
1.4139"
87.8 to 87.9
0.7547 40
1.4147
@ 755mm
p20
@18
87.2 to 87.9 9
0.7552 44
1.4125 e
@ 748mm
jP to
W H a
0.7590 9
1.4240*
cfs-1 ,2-Dimethyl-
0.7723
cyclopentane
c
-62
99.25
0.7718
1.42014 fl
A/
99.23 lfl
0.77266 16
^V
98.40
0.7764 6
1. 42748
\ /
@ 741mm
@15
W S
1.43180
1.42202
w 20
V
C,H, 4
60
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
z>r
s
Additional Data
trans-l ,2-Dimethyl-
cyclopentane
-120
91.8
0.7495
1.40934'
91.78"
0.75137 "
w 20
90.95
0.7541
1.41659
@ 741mm
@15
""B
1. 42077 a
^20
1.41155
%
1,2-Dimethyl-
cyclopentane
-119.0 60
92.7 to 93 <
0.7664 6 - 57
1.4187"."
@ 762mm
0.766 9
1.417"
95.8 to 97.6 8
0.764
1.41745"
94 to 99
0.7613
1.4126 40
94 to 98 68 - 67
0.7681 8
1.4160"
93 to 94 49
@15
1.4150"
92 to 95 "
0.7534 40
@ 18.5
92 to 93 <
/>o
1.4166 68 ' 69
@ 758mm
0.7629
w l?
94 to 96 40
Do 20
1.4241 M - w
@ 754mm
0.7581 40
1.4287 W W
61
C,H 1(
Name and Carbon Skeleton
M. P.,C
B. P. t C.
@ 760mm
iff
5
Additional Data
<M,3-Dimethyl-
cyclopentane
[] +i f 78i
c
90.5 to 91 e
0.7497 M
1.4110
A
@ 755mm
@18
@18
U
C
1,3-Dimethyl-
cyclopentane
-136.75 s
93 65
0.7410 w
1.4066"
-136.7
90.7 8
24
@24
69a
90.68 to
0.7463 1J> ' 26
1.4076 38
90.80
0.7543 65 - 78
20.8
90.6 to 90.8 3 - 6
0.7562 3J>
1.4096 19 - 25
90.5 19 - 26
Z>J
1.4130 78
94 to 95 39
0.7456 3 - 8
1.4144
@ 755mm
@ 19.7
1.4104 3 ' 5
91 to 91.5
0.7498 3 - 6 - 8
@16
@ 751mm
@15
90. 18 to
0.7504 J9 - 26
90.30 3
@15
@ 749mm
89.9 to 90.1 3
@ 744mm
9373
@ 743mm
x,jt-Dimethyl-
cyclopentane
91 to 94 "
91 to 91.4 7
62
Name and Carbon Skeleton
M. P.,C
B. P. C.
@ 760mm
D?
-5
Additional Data
Propylcyclopentane
130.8
0.7765
1.4265s
(IT)
sa 000849/C
c-c-c
-120.3 7
131.3'
0.7601 "
1.4256"
* (15 to 40)
-121.7
69a
to 13 1.5
130.7 "
130.6 1 - 29
40
0.7755
21
22
1.4259 73
21
~- ~0.000461/C.
(-30 to +25)
129.5
0.7772 7
1.4263 62
754mm
20.2
1.4266 7
130 to 131.5 73
0,7718 18 - M
fw,
751.3mm
0.7756 "
1.4269J".
126 to 128"
0.7766
61
@ 739mm
0.778971,73
1.4270 71 - 78
16.5
16.5
0.7812 .
1.4289"
15
14.7
0.7814 '
1.4329"
14.9
6.8
1.4353
1.4480 M
-26.3
1.42285 "
1.4245 7
^19.9
1.43040 "
n S
1.4319 7
1.43474 18
i
1.42470"
63
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D?
n
Additional Data
Isopropylcyclopentane
0.7766
1.4264
^--OOOQ86/-C
c-c-c
-112.7 6
126.8 61
128 to 129 18
0.7593 61
@40
1.4252"
@22
dt (15 to 40)
@ 754mm
123 to 124"
0.7717 18
0.7764 61
1.4261 61
1.4273"
dt (-25toH-25)
@ 731.6mm
0.77640 "
@18
0.7785 * 7
1.4284"
18
@15
1.4317"
@7.7
1.4468"
@-26.3
1.42255"
1.43010"
H H
1.43454"
t,
1.42470 "
c/s-l-Methyl-2-ethyl-
cyclopentane
0.7850,
~~- -0.000802/C.
(0 to 20)
c
1 c-c
o x
128.24 to
128.26"
127.7 to 128"
0.78508
0.7846 "
0.8011"
1.4291 "
1.4269"
n H
\ /
@0
1.4344"
n H
1.4387"
n ff.
64
Name and Carbon Skeleton
M. P.C.
B. P., C.
@ 760mm
Iff
"S
Additional Data
frans-l-Methyl-2-
ethylcyclopentane
0.7691
dt (0 to 20)
121,4 to
0.7696 13
1.4220 13
121.75 13
0.76912 "
1.4198"
121.35 to
0.7860 13
n a
121.40 "
1.4272 l3
1.4314"
n a
l-Methyl-2-ethyl-
cyclopentane
f
124 48
0.7728
1.42835"
121 < 9
@ 753mm
d-l-Methyl-3-ethyl-
[a] D - 4-4.34 6
cyclopentane
c
120.5 to 121 6
0.7669
1.4214*
6
756mm
16
@16
\
c-c
Name and Carbon Skeleton
M. P.,C
B, P .. Cf
760mm
Iff
D
Additional Data
1,1,2-Trimethyl-
cyclopentane
0.7710 4
^=-0.000869rC.
* (0 to 25)
(Dihydroisolaurolene)
11474,75
0.7694 17
1.4199 41
C C
11474
D 25
1.4234 74
6C
@ 755mm
0.7727 17
19
/
113 to
>20
1.4238 74 - 76
113.5 17 - 41
@ 750mm
0.7661 41
18
1.4223 74
113 to 114 4I
749mm
0.7719 74
17
fl7
@ 19
1.42244 21
0.7728 74 - 76
W 16.2 L
0.7686 74
f.7
1.42998J,,,
@ 17
wj? * 2
0.7746 21
8
@16.2
0.77463 17
fl7.
1.43398U
@y 16.2
w^
0.7762 17 - 41
D 15
0.7706 41
0.7800 17
n 10
0.7847 17
4
1,1,3-Trimethyl-
cyclopentane
c c
15 to 116 81
0.7703 81
1.4223 81
c
66
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
iff
1.5
Additional Data
1,2,3-Trimethyl-
cyclopentane
(Dihydrolaurolene)
114toll5 74 ' 76
111.5 to 114 I7
0.7567 > 7
D 26
1.4230 74 - 76
@19
C
1 c
0.7596 17
D 20
1.41424J^
\
c
0.7588 l7 - 21
@ 19.8
0.7688 74 - 76
fn,
1.42162J 21
0.7633 17
f
1.4259l( 21
0.7718 17
T
C,H 18
Butylcyclopentane
c-c-c-c
6
- 108.2 7
-112.1
60a
154.5 to 156 86
@ 762.7mm
157.2 l0 ' 25
156.8 7 ' 51
154.5 to 155 62
0.7843
0.7687 "
0.7848 7
0.7832 M
1.4315
1.4309 62
@21.9
1.4314 7
@20.2
1.4310 19 - 25
^=-0.000781/C.
rf (15 to 40)
^=-0.000460/C.
(-30 to +25)
@ 750mm
0.7847 19 - 25
1.4315 82
0.7862 w
1.4317"
@16
1.4336"
0.7886 w ' 2&
16
@ 15
1.4336 6J
0.7887 7
@ 14.8
@ 14.95
1.4380 58
1.4529 88
1.4292 '
* 20. 36
"*.
1.4366 '
w *; 4
67
Name and Carbon Skeleton
M. P, t C.
B. P., C.
@ 760mm
iff
5
Additional Data
2-Cyclopentylbutane
c-c-c-c
6
154.6 "
152.5 to
@ 763.7mm
0.7944 6
0.7787
@40
0.79407
0.7941 61
1.4362
1.4356"
@21.3
1.4361 61
1.4370*-"
^~=-0.000790/C.
(0 to 40)
* (-25 to 25)
151 to 152 62
@ 741mm
0.7971 3 ' 37
@18
1.4386"
152tol54 fl3
@ 725mm
0.810 "
@ 14.7
1.4415"
@7.8
1.4554"
@-26.3
2-Methyl-l-Cyclo-
pentylpropane
c
1
c-c-c
148 to 149 18
@ 756mm
0.7795 18
1.42738 18
1.43516"
n H
1.43980"
n M
1.42950"
2-Methyl-2-cyclo-
pentylpropane
rf/ (20 to 40)
(terJ-Butylcyclopentane)
-96"
145.2
0.7753 61
1.4342
C
I
0.7911"
1.4341
1.4320
c~c-c
1
w ^ a
o
1.4396"
68
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
5
Additional Data
cte-l-Methyl-2-propyl-
cyclopentane
** (0 to 20)
c
1 c-c-c
a
-104.9"
152.58"-"
r
0.79212J 19
0.80783 "
1.43432"
1.432 IP 5
1.43962 16
1.44395"
1.43858"
tz 20
"',
1.43171"
1.43442"
*rans-l-Methyl-2-
propylcyclopentane
0.7774 3
^ (0 to 20)
146.37 "
0.7774 M
1.42740"
146.37 to
0.77743 16
1.42526"
146.38 16
0.79328
n a
@0
1.43279"
n a
1.43705 "
^20
y
1.43173 "
tf'20
X
1.42496"
1.42750"
*.
69
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
iff
<
Additional Data
l-Methyl-2-isoprogyl-
cyclopentane
c f
142.5
0.7792
1.4279
1 1
@ 759mm
Dj
/\/ c - c
0.7833
\J
D?
l-Methyl-3-propyl-
cyclopentane
c
146 to
148 70
O
@742mm
\
c-c-c
l-Methyl-3-isopropyl-
cyclopentane
c
140 to 142.5 36
0.7730 62
1. 4236
1
@ 764.8mm
@22
@22
142 to 144 62
0.7792
1.4279 43
133 to 134 80
0.773 3
1.4250 30
\
132 to 134 30
@ 19
@19
C C
1
142.5 43
0.7750 38
1.4257"
c
@ 759mm
18.5
@ 18.5
141.5 to 142 22
0.7799 M
1.42744"
@ 758mm
@15.2
w]J- 2
a
1.43505 22
1.43947"
i
70
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
DP
2
Additional Data
1,1-Diethylcyclo-
pentane
oc c-c
6
150.5 <*
@ 757mm.
0.8028
DT
1.4388
cis-1 ,2-Diethylcyclo-
pentane
dt (0 to 20)
c-c
-118.7"
153.55 to
153.58 "
0.79599J",'
1.43552"
1.43562"
\_f
153.58 "
0.81165"
1.43332 "
1.43343"
1.44090"
n u
1.44100"
1.44528 M
7
1.44538"
v
*ran$-l,2-Diethyl-
cyclopentane
rf/ (0 to 20)
-95.6"
147.53 "
0.78316"
1.42950 "
147.53 to
0.78318 "
1.42738"
147.55 "
0.79858 "
nj^
@
1.43487 "
1.43920"
7
71
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
s
Additional Data
1,2-Diethylcyclo-
pentane
151 to 152
0.7952
1.4353
@ 755mm
Iff
1,3-Diethylcyclo-
pentane
c-c
148 to 149
0.7851
1. 4298
1
@ 767mm
Z) f
\
c-c
1 , 1 ,2 ,3-Tetramethyl-
cyclopentane
c c
5~
0.7820
1.42781 21
(j
/
@14.1
a
1.43541
nj}jj
c
1. 43986 21
7
72
Name and Carbon Skeleton
M, P.,C.
B. P., C.
@ 760mm
DT
"8
Additional Data
3-Methyl-l-cyclo-
pentylbutane
c-o-c-c
171 to!72 3
0.7837 32
1.4321 32
1 1
o
168 to 170"
25
0.7868 3
@ 20.5
@25 C
1.4340 8
@20.5
2-Cyclopentylpentane
c-c-c-c-c
1
177.5 62
0.7955 "
1.4438 62
dt (20 to 40)
1
frtlAf)
O
\y T:V/
0.8099 62
3-Cyclopentylpentane
c-c-c-c-c
1
174 to 176"
0.81 16 3 '
1.4443 37
O
73
Name and Carbon Skeleton
M. P. t C.
B. P. t C.
760mm
iff
8
Additional Data
2-Methyl-2-cyjclo-
pentylbutane
1.441 7
~ =-0.0007 4 /C.
(20 to 40)
c
i
173.9 61
0.7923 &1
1.4412 62
-^=-0.00043 4 / C.
1
c-c-c-c
40
21.3
(-25 to +20)
1
0.8071 61
1.4457 "
o
1.4439 62
14.6
1.4470 62
7.7
1.4619 62
-26.6
1.4433 61
1.4511 61
l-Methyl-3-butyl-
cyclopentane
c
i
170.2 8
0.7840 8
1.4321
1
@ 750.7mm
15
15
1.4298 8
n " n
c-c-c-c
1.4418 8
7
74
Name and Carbon Skeleton
M. P.,C
B. P., C.
760mm
Of
w s
Additional Data
1 ,2-Dimethyl-3-iso-
propylcyclopentane
Kasansky (33) claims
that the compound
prepared by God-
c
148 to 149
0.7877
1.4319 36
chot and Taboury
1 c
146 to 148 30
@21
21
(29) [which is the
\ /
161.4 to
0.7883
1.4328*
same compound as
\
oc
1
161.9"
758mm
159 to 160.5 > 5
0.786
@21
1.4344"
16.5
thatofGodchot(28)J
is not 1,2-dimethyl-
3 -isopropy Icy clopen-
tane.
c
757.6mm
0.793 27
1.4337"
159 to 161 35
@ 15
16
@ 757mm
0.7929 H
1.4364"
49.5 to 49.8 5
@15
15
@ 14.5mm
Hexylcyclopentane
C-(C) 4 -C
204 to 206 7
0.7903
1.4370 w
6
@ 748mm
1 ,2,3-Trimethyl-4-iso-
propylcyclopentane
c
157 to 158"
0.7833 27
1.4326"
<V
13-
13
X
c-c c
1
1
c
75
Name and Carbon Skeleton
M. JVC.
B. P., C.
@ 760mm
Iff
5
Additional Data
l-Methyl-2,3-diiso-
propylcyclopentane
c
150 to 152 80
0.781 80
1.4318"
C |
1 c-c
17
@17
c-c
1
c
Octylcyclopentane
C-(C) 6 -C
1
133 to 134
0.8156 7
1.4483"
o
@ 26mm
@18
C 17x134
Dodecylcyclopentane
C-(C)io~C
175 '
0.8280
1. 45737
6
@ 15mm
18
76
(1) J. v. Braun, E. Kamp, and J. Kopp, Her. 70, 1750, 1937.
(2) J. H. Bruun and M. M. Hicks-Bruun, J. Research Nat. Bur. Standards, 10, 465, 1933.
(3) G. Chavanne, Bull. sci. acad. roy. Belg. [5] f 12, 105, 1926.
(4) G. Chavanne, Bull. soc. chim. Belg. 31, 331, 1922.
(5) G. Chavanne, Bull. soc. chim. Belg. 35, 283, 1926.
(6) G. Chavanne, Bull. soc. chim. Belg. 39, 402, 1930.
(7) G. Chavanne and P. Becker, Bull. soc. chim. Belg. 36, 591, 1927.
(8) G. Chavanne and O. Miller, Bull. soc. chim. Belg. 39, 287, 1930.
(9) G. Chavanne, 0. Miller, and Cornet, Bull. soc. chim. Belg. 40, 673, 1931.
(10) G. Chavanne and L. G. Simon, Compt. rend. 168, 1111, 1324, 1919.
(11) G. Chavanne and L. de Vogel, Bull. soc. chim. BeJg. 37, 141, 1928.
(12) G. Chavanne and H. Van Risseghem, Bull. soc. chim. Belg. 31, 87, 1922.
(13) G. Chiurdoglu, Bull. soc. acad. roy. Belg. 17, 1404, 1931.
(14) G. Chiurdoglu, Bull. soc. chim. Belg. 42, 347, 1933.
(15) G. Chiurdoglu, Bull. soc. chim. Belg. 43, 35, 1934.
(16) G. Chiurdoglu, Bull. soc. chim. Belg. 44, 527, 1935.
(17) A. Crossley and N. Renouf, J. Chem. Soc. 89, 26, 1906.
(18) F. Eisenlohr and G. Gorr, Fortschr. Chem. Physik. physik. Chem. B18, No. 9, 10, 1925.
(19) E. B. Evans, J. Inst. Petr. Tech. 24, 321, 1938.
(20) J. Eykman, Chem. Weekblad, 1, 7, 1903.
(21) J. Eykman, Chem. Weekblad, 3, 685, 1906.
(22) J. Eykman, Chem. Weekblad, 8, 651, 1911.
(23) J. Eykman, Naturkundige Vorhandelingen Haarlem [3], 8, 505, 1919.
(24) P. Freer and W. Perkin, Jr., J. Chem. Soc. 53, 202, 1888.
(25) F. Garner and E. Evans, J. Inst. Petr. Tech. 18, 751, 1932.
(26) M. Godchot, Bull. soc. chim. [5] 1, 1153, 1934.
(27) M. Godchot, Compt. rend. 172, 686, 1921.
(28) M. Godchot and G. Cauquil, Compt. rend. 191, 1326, 1930.
(29) M. Godchot and F. Taboury, Ann. chim. phys. [8] 26, 41, 1912.
(30) M, Godchot and F. Taboury, Compt. rend. 156, 470, 1913; Bull. soc. chim. [4] 13, 599, 1913.
(31) A. V. Grosse and V. N. Ipatieff, J. Org. Chem. 2, 447, 1937.
(32) J. Harris, J. Am. Chem. Soc. 51, 2591, 1929.
(33) M. M. Hicks-Bruun and J. H. Bruun, J. Research Nat. Bur. Standards 7, 799, 1931.
(34) C. J. Jacobs and G. S. Parks, J. Am. Chem. Soc. 56, 1513, 1934.
(35) B. A. Kasansky, Ber. 62, 2205, 1929.
(36) B. A. Kasansky and A. F. Plate, Ber. 69, 1862, 1936.
(37) B. A. Kasansky, A. F. Plate, and K. M. Gnatenko, Ber. 69, 954, 1936.
(38) N. Kishner, J. prakt. Chem. [2] 56, 364, 1897.
(39) N. Kishner, J. Russ. Phys. Chem. Soc. 37, 516, 1905.
(40) N. Kishner, J. Russ. Phys. Chem. Soc. 40, 676, 994, 1908.
(41) N. Kishner, J. Russ. Phys. Chem. Soc. 42, 1211, 1910.
(42) N. Kishner, J. Russ. Phys. Chem. Soc. 43, 1149, 1911.
(43) N. Kishner, J. Russ. Phys. Chem. Soc. 44, 854, 1912.
(44) N. Kishner, J. Russ. Phys. Chem. Soc. 45, 973, 1913.
(45) N, Kishner and Amasow, J. Russ. Phys. Chem. Soc. 37, 518, 1905.
(46) W. Markownikoff, Ber. 30, 1222, 1897.
(47) W. Markownikoff, J. prakt. Chem. [2] 49, 409, 1894.
(48) T. Marshall and W. Perkin, J. Chem. Soc. 57, 241, 1890.
(49) C. D. Nenitzescu and G. G. Vantu, Bull soc. chim. [5] 2, 2209, 1935.
(50) G. S. Parks and H. M. Huffman, Ind. Eng. Chem. 23, 1138, 1931.
(51) H. Pines and V. N. Ipatieff, J. Am. Chem. Soc. 61, 1076, 2728, 1939.
(52) H. Pines and V. N. Ipatieff, Unpublished data.
(53) F. Richter, W. Wolff, and W. Presting, Ber. 64, 871, 1931.
77
(54) N. A. Rosanow, J. Russ. Phys. Chem. Soc. 47, 591, 1915.
(55) L. Ruzicka, M. Stoll, H. Huyser, and H. A. Boekenoogen, Helv. Chim. Acta, 13, 1152,, 1930.
(56) M. van Rysselberge, Bull. soc. acad. roy. Belg. 12, 171, 1926.
(57) M. van Rysselberge, Bull. soc. chim. Belg. 35, 311, 1926.
(58) J. Smittenberg, H. Hoog, and R. A. Henkes, J. Am. Chem. Soc. 60, 17, 1938.
(59) R, Thiry, These, Brussels, 1925.
(59a) J. Timmermans, Bull. soc. chim. Belg. 36, 502, 1927.
(60) J. Timmermans and Hennault-Roland, J. Chim. phys. 34, 693, 1937.
(61) A. I. Vogel, J. Chem. Soc. 1938, 1323.
(62) O. Wallach and E. Meyer, Ann. 392, 58, 1912.
(63) R. Willstatter and M. Heidelberger, Ber. 46, 517, 1913.
(64) J. Wislicenus and W. Hentschel, Ann. 275. 322, 1893.
(65) N. D. Zeliasky, Ber. 30, 387, 1897.
(66) N. D. Zelinsky, Ber. 35, 2677, 1902.
(67) N. D. Zelinsky, Ber. 44, 2781, 1911.
(68) N. D. Zelinsky, J. Russ. Phys. Chem. Soc. 31, 408, 1899.
(69) N. D. Zelinsky, J. Russ. Phys. Chem. Soc. 38, 625, 1905. -
(70) N. D. Zelinsky, Private Communication, Beilstein V, Suppl., 18, 1928.
(71) N. D. Zelinsky and B. A. Kasansky, Compt. rend. acad. sci. (U.R.S.S.) 3, 168, 1934.
(72) N. D. Zelinsky, B. A. Kasansky, and A. F. Plate, Ber. 66, 1415, 1933.
(73) N. D. Zelinsky, B. A. Kasansky, and A. P. Plate, Ber. 68, 1869, 1935.
(74) N. D. Zelinsky and N. Lepeschkin, Ann. 319, 303, 1901.
(75) N. D. Zelinsky and N. Lepeschkin, J. Russ. Phys. Chem. Soc., 33, 555, 1901.
(76) N. D. Zelinsky, S. E. Michlina, and M. S. Eventowa, Ber. 66, 1422, 1933.
(77) N. D. Zelinsky and A. Moser, Ber. 35, 2684, 1902.
(78) N. D. Zelinsky and M. Rudsky, Ber. 29, 403, 1896.
(79) N. D. Zelinsky and M. Rudsky, J. Russ. Phys. Chem. Soc. 31, 408, 1899.
(80) N. D. Zelinsky and M. B. Turowa-Pollak, Ber. 65, 1171, 1932.
(81) N. D. Zelinsky and A. Uspensky, J. Russ. Phys. Chem. Soc. 45, 837, 1913; Ber. 46, 1470 (1913).
78
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
DT
ng
Additional Data
Cyclohexane
80.7,
0.7781,
1.4264.
j- 0.0002548 y
O
4.5 30
4.7 "
5.95 "
6.10"'
6.2 M
67 tn
81.06
764.59mm
80.2 "
763mm
81 to 82.7
81 to 81. 5 >o
0.72056 JM
80
0.72215 w
78.05
0.73057 1M
70
1.4235
25
1.42370 >
25
1.4274*
25
degrees/(40mm to
760mm)
j<-r
~~- 0.0420 degrees
/mm at boiling point
(P - 760mm)
. tu
6.4 1M
81 ",i50
0.73997 lw
1.4275 18
Average value of -jr
6.25 *
80.93
60
25
between 740 and 760
QA n 24 3(ki
0.74060 1M
1.4242
mm.
6.28 * l
so. y Z4>8< *
6.34 M
80.8 to
30.9 n.ieo
60
0.74416 w
1.4254 M
1.4262
= 0.0425 degrees
/mm.
{4 IM
0., M
80.80 l8 '
@ 50.95
1.4263 18
^r-- 0.000972,
6.40 13e
80.8 .",,
0.74957 1M
.42636
(1-0.000234 6 0/C.
6.45
80.6 to 80.8 *
0.75513 1M
.42648
(7 to 80)
dn
6.48 33
[29,106,
80.0 to 80.2 *
80 *
44.6
0.7555 6
.4265
.42656 46
~~ -0.000470 4 /C.
dt (10 to 25)
6 ' 5 {m
79 to 80 10
44.6
.4266 M
Gifford and Lowry 31
6.55
79131
0.7564 " 6
.42691 >
have determined the
6.7 *
78.5 to 79.5 127
43.6
.427
index of refraction of
80.8 1M
0.7570 '
.4275 lo
cyclohexane at 15
759.75mm
80 to 80.5 38
759.5mm
42.9
0.75942 w
40.21
.4266 1M
19.5
1.4269 1 "
for various wave
lengths and have
summarized their re-
sults in the follow-
80.5 >
0,75907 156
18
ing dispersion
@ 758mm
40
1.4271 123
formula
80.5
0.76853 166
17.5
@ 756mm
on </v SO
0.7692 ll
1.42446*'
17.4
(wj 8 ) 2 - 2.01 1046
0.0102467
OU.OO * g
755.69mm
30
1. 42806 4
+ X a - 0.013977
(3282A to 7701 A)
81 lOMi*
0.7730 I4B
16.1
755mm
25.6
1.42886 18
Similarly, Lowry and
80.5 to 80.7
0.77384 M
15
Allsopp 67 have
755mm
25.08
1.429001 31
studied the depen-
80.65 1M
0.77354 " 7
15
dence of index of re-
754.7mm
79 to 79.5
25
0.7737 M
1.4371 127
11
fraction upon wave
length. Their equa-
@ 752mm
25
1.43119
tion is
72 to 73
0.7741 M
10.85
(")- 2.00519
752mm
25
1.42225 **
0.0098035
80.3 n
0.7694
W S
+ X- 0.01 1923
@ 750mm
DS
(2450A to 6707A)
79
Name and Carbon Skeleton
M. P.*C.
B. P., C.
@ 760mm
0T
ng
Additional Data
Cyclohexane
(Continued)
80.0 166
0.7758 '
1. 42437
@ 74 1.3mm
@22.4
"S.
80.5 to 81 17S
@ 740mm
0.7772
@20.8
1.42476"
80. Ho 80.2 "
0.7763 "
@ 738mm
0.7769 .i"
1.42211"
79 to 79.5 151
[24,
n a
@ 723mm
0.7775J 8 *.
1.42589*
75.37 "
I"
W B' 1
@ 646.0mm
0.7780 146
1.42698"
70.0 I55
0.7782 M
n a
@ 540.8mm
60.0 "
0.7783 M
0.77849 I2
1.42777"
@ 385.0mm
0.7786 90
n- 8
19.78 98
@ 78.40mm
0.7788 89
1. 42910
w^- 86
18.44 s0
0.790 "
@ 70.71mm
0.7731 29
1.4297 1 23
6.90 "
D 20
-^20
n a ft
@ 40. 60mm
0.7727 72
1.43184"*
6.1498
Z> 20
n
@ 38. 70mm
0.7788 '"
1.43229"
@ 19.5
w //
0.7808 112
^
1.42960 2
0.781 >
nV Hp
@18
1.43345 4
0.7834 1M
ng-J
@ 17
1. 43447"
0.78221
w lfi
16.12
H /8
0.7808 4
1.4353 1
0.7820 2 *
1.43668*
@16.1
w 10.86
0.7824 M
1.43415"
@ 15.9
*25
0.7820 24 ' 3(>a
r
@15
1. 43580
0.78224 "
M / r
@15
80
Name and Carbon Skeleton
M P r
IrJL . JL , t U
B. P., C.
@ 760mm
Iff
g
Additional Data
Cyclohexane
(Continued)
0.7830 l
1.43668"
@ 15
y
0.78310 13
1.43391 29
@ 15
**17 4
0.7771
n H
>JJ
1. 43773 4
0.774 72
wj^
rxl6
1. 43892 23
0.78280 I6B
7
14.5
1. 43972 2 *
0.78435 "*
jg_5
/7?) 1 1 1
y
Vj*# 1O.O
1.44116 5
0.7844 28
@ 13.5
7
0.7869 5
1.5232 142
@ 11.2
W 16. 8
0.7875 127
1.4388 142
11
M 16 - 3
W 4200
0.7872 5
@ 10.85
0.78715 155
@10.7
0.7812 2
7} 10
0.79063 "
7.00
0.7865
0.7903 M
0.7967 '
0.8352
0.7902 72
81
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
tif
-8
Additional Data
Methylcyclohexane
100.3
0.7692 7
1.4230,
~--0.000857/C.
c
6"
-126.3
100.0 2
0.7174 2B
1.4198*
(0to80)
119,128,132
780mm
78.8
1.4227"
^= -0000481/C
- 126.4
100.4 to 14fi
0.7344 146
1.423
rf/ (10 to 20)
128,135,136
100.7
62.1
[-43.
148
773mm
0.7512 145
1.4230J 89 '
The density and re-
-126.7
100.0 "
42.1
fractive index values
137
-126.85
134
-1 26.9 s8
770mm
100 146
@ 770mm
103"
0.76030 13fl
@30
0.7606 "
30
1.42306"
1.4231
1.4232 1W
1.4239 * 4 .-
of Eisenlohr and
Gorr (ref. 23) are
each the mean of
five separate deter-
minations reported
102
101.20 138
0.7679 **
143,145
1.42410 **
149,149
in the paper.
101.1
101 to 41 - 123 - 168
102
fl,68,
0.7687( 89
0.7688 137
1.4243
19
**Vogel (ref. 143,144,
145) reports the
existence of three
1Q1 3,133,134
101.0 24 ' 8to
0.7689 10
0.7693 159
1.41705"
18.5
1.4243
isomeric liquid forms
of cyclohexane, the
individual constants
100.8 to 117
0.7694 **
18
of which are given in
100.9
144,145,169
1.4242 1M
the tables.
100.8 12 '
0.76944 148
17.6
100.80 " 8
0.7696 24 - 30B
1.4235 "
100.4
0.7697 73
17.5
100.30 136
0.7704 **
1.42531 *
100 to 101 "i
148,145
15.5
100 30ft
0.77304 * 23
[43,
99.8 to
0.769 8
1.42535 a
100.8 "
Dlo
(& 10 [
99.4 to 102 89
0.7641 63
1.4291 m
11
99 to 101 10
D}
1.39116"
98 to 100 > 27
0.7695 43
ftl*.*
99.5 to
Dl
100 *' 146
0.7622 M
1.42081 **
@ 759mm
18.5
143,14*
100"
0.7647 1M
*X
@ 758mm
18
1.42085 l
100.5 4
0.7662 "
wg-
754mm
18
fill
100.2 "
0.7718
1.42093| 146
@ 75 1mm
@ 16.9
W S*
a
0.7725
16.3
82
Name and Carbon Skeleton
Mjy Of
. JT., L.
B. P., C.
@ 760mm
DT
"8
Additional Data
Methylcyclohexane
(Continued)
100.3 to
100.9 M
0.7773 *
fitt.
1.42167| 14S
@ 745mm
0.77340 1SW
ng- 00 **
100 to 100.2 '
@ 15
1.42311 23
@ 742mm
0.7736 24 ' 308
w 20 *
(fh 1 5
a
0.7737 18
1. 42296 26
@ 15
a
0.774 w
1. 42330 $6
^!s
w u.
0.7693
1. 42308 4
0.7738 a2
1.39816 26
J^isis
wg- 8
0.7791 l27
^
1. 42838 148
(gj 11
w w.oo
0.780
@0
1.42839**
0.7859 112
143,146
@0
H 'l
0.78640 136
1.42846**
@0
144, 1
0.78650 13fl
W 20-0
@0
* fl43
0.7868 "
^t^J 146 '
0.7804 M
1.43082 23
rt
0.7859
1.43053 M
0.7887 42
W */j
/>!
1. 43088 2fi
1. 43058 4
1.40230 **
^78.8
7
1.43230J',"'
r
7
83
C,H 14
Name and Carbon Skeleton
Mp or<
-L <} lx.
B. P., C.
@ 760mm
d
s
Additional Data
Methylcyclohexane
(Continued)
fl44
1.43250{ I4S
ti
y
1,43285 l48
w jj*
y
fl44
1.43301 m
W S'
y
1.43524 2I
fj20 4*
1
1.43498"
7
1. 43533 *
1.43502
1.42540 *
C!l id
84
Name and Carbon Skeleton
M. P.,C.
B. P., a
760mm
D?
-B
Additional Data
Ethylcyclohexane
31.8
.7878,
.4329 a
-^- ~0.000770/C.
c-c
111.40
32 to 134 "
.7899 l
.4278
tf (0 to 20)
97
31.89
25
25
-- -0.000436/C.
128.9
31.8 188
.7771
.43079 w
' (10 to 25)
133
31 6 24 - 8to
.7840 "
25
31 to 132
.7854 '
.4320 *'*
30.1 to
.7872 M
.4324
130.7 "
T Q *7 C Si 30a
./O/O "''"*
.43283 M
30 " 2
.78804 7
.4329 J0
28.5 to
.787 8
.4332 " 8
130
D 80
.4343
28tol29 l
.793 "
.436"
29.5
17
17
756mm
.7914 M 30R
.4373 i
32 to 133
15
11
755mm
.7972 127
.43041 23
30 to 13 1 M
11
W ^
751mm
.7997 87
.43803 23
30 to 132 M
n H
745mm
29.8 to 130 l
.8025 112
.44272 M
n*
743mm
.8026 ni
a y
28 1M
'
.43251 23
724mm
0.7913
85
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
z>5
-B
Additional Data
1,1-Dimethyl-
cyclohexane
119.,
0.7810
1.4293
-j-- -0.000804/C.
(0 to 25)
c c
5
-35.1"
120"
@ 766mm
118 to 1 18.5 80
0.7798
0.7786 "
1.4285 17
1.4289
~- -0.000355/C.
(10 to 25)
^^
@ 764mm
@21
1.4342" 3
121.2 to
0.78073 w
@18
121.8"
0.7820 IM
1.4351 *
120 M ' M
0.7825 M
@17.6
119.7 to
119.980
0.7832 M
1.4314"
119.2 to
119.7 1M
0.7890 M
1.4320 1M
@17.6
u#
118.5 to
120 " 3
0.7843 "
1.42958"
119.2 to
119.770
@16
0.775 "
a
1.4290"
n l j.
@ 752. 8mm
\& 10
119.5 to
0.7840 "
1.43728"
120"
@15
W 15.6
751mm
0.7864 "
1.44203
^16
ft"-*
0.7947 "
7
@4
1.4413"
0.79709 M
n l f f
@0
1. 42359
n H0
1.42680 M
r
1. 42635
*
1. 42959 80
1.43489 w
1.43822"
tjlS.8
**%
86
Name and Carbon Skeleton
K/T U /~*
M. r., L.
B. P., C.
@ 760mm
*
-S
Additional Data
czs-l,2-Dimethyl-
cyclohexane
0*7965
~- -0.000784/C.
tfi (0to30)
c
("78,
130.26 78
130.04 7
0.7891
1.43114 1 *
1.4333 7
| J
-57.5"
128.4 to
0.7822 2 3
1.43369 7B
^s<
129.5 "
0.786 12 <
n* M
128.3 to
128.7 187
0.7868 23
0.7905 " 7
1.43373
126.5 *
126.5 2a
@ 750mm
0.79620 78
0.79625 79
0.8015 14
a
1. 42859 tt
3.
@ 15
1.43050
0.8016 18
s.
15
1. 43669
0.81125 78
W 13.78
a
0.8131 1 80
(7f\ f\O
1. 44133
\3? *J
1.44138"
Tj^.30
1.43635
1. 43823 M
g
1.44439"
W W.7
1.44585"
1. 44088 n
y
1.44271 23
1.44897"
n UM ^
1.43060 23
1.43241
87
C,H,,
Name and Carbon Skeleton
KJf "D o/"*
M, jT M 0.
B. P., C.
@ 760mm
Df
-8
Additional Data
ci's-l,2-DimethyL-
cyclohexane
(Continued)
1.43061 80
1. 43387 80
1.4334380
V
1. 43598
W 20.30
n He
V
1. 43599 79
w w
?/
*w
1.43901 78
"/
1.442 II 80
1. 44548 80
%
C g XI 16
88
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@, 760mm
D?
4
Additional Data
trans-1 ,2-Dimethyl-
cyclohexane
0.776
1.4303
dt (0 to 20)
-89.4"
125 m
0.7760 "
1.42930"
-89.6"
124.5" 2
0.77601 "
1. 43020 in
124' 24
0.779 >
1.43037 "
123.9"
0.7798
1.4305"
1 23.85 78
0.780 12 <
1.4326 187
123.70"
0.781 1 71
1.42466"
123.42 to
0.7814"
wg- w
124.17 7I
0.7822 127
1.42470"
122.5 to
123.5 121
121.3 to
121.5"
126 to
126.5 " 7
@ 758mm
124.5 2 *
0.7823 iw
0.7920 to
n ll.4
Dli.4
0.79188 80
@o
0.8008 in
n ff -^
1.42778"
W 5J
1.42768"
n !3.8b
1.43224"
@ 755mm
122.5 to 124"
H P
1.43230"
@ 748mm
W 206
1.43546"
1.43533"
ng-"
1.4365"
w"-"
Y
1.43673"
ng-
1.44008"
1.43979"
1.42990"
20
1.42171
r
1.42493 w
89
Name and Carbon Skeleton
\f p or<
lu. Jr., U.
B. p., a
760mm
D?
Additional Data
frans-l,2-Dimethyl-
cyclohezane
(Continued)
1.42443 *>
*
1.4269S "
-
V
1.42701
*v
1. 42768 M
1. 42999
*w
1.43331 M
1. 43641 M
n 8?
90
Name and Carbon Skeleton
ir p or*
M. jr., U.
B. P., C.
@ 760mm
iff
s
Additional Data
1,2-Dimethyl-
cyclohexane
128.6 to 129 17
0.780 12 <
1.4266 162
127.9 2 <' 30 *
0.7874 2 - 30 *
1.4292 3
126.5 124
0.792 8
1.4314 24 ' 30 "
126.4 to
DjJ
1.4332 118
128.9 8
0.7809 3
1. 43020
126 112
@ 17.85
@ 17.85
125 m
0.791 2 24,30a
1.4347 127
124.5 162
@15
@ 11
124 1W
0.798 17
1. 42820 3
^17.85
123 to 125 127
vgj 10
122.5 to
123.5 3
0.7880 27
@ 14.25
1.43 134 27
124.5 27
0.7929 127
a
1.43592 s
@ 73 1mm
0.8008 n2
n
@0
1.43901 27
0.8002 10
W H.26
Dl
1. 44056 3
y
1. 44342
W .H.26
a
91
C,H 1(
. Name and Carbon Skeleton
jtf p r
MM. , JT ,j \s*
B. P., C.
@ 760mm
D?
-8
Additional Data
cts-l,3-Dimetbyl-
0.783s
dD _ oooog e
cyclohexane
rf ' (0 to 20)
c
-86 to
124.9 80
0.7613 ' 8
1. 42609 4
-90 14
123.5
@30
1.4265 88
-100 80
121.5 12 <
0.7735 28
1.4269 121
\
121 to 122 "
0.774 121
1.42385 2 >
c
121.0 28
0.775 12 <
n $ a
121 121
0.777
1.43170 23
11 9.5 to
0.78348 M
H H
122.3"
0.7728 '
15
1.43628"
0.7759 "
v
@15
1. 42600 23
0.7852 I8
n *
/Ov rjo
(&> U
1.42495 80
0.80022 80
n 26.4
@0
r
1. 42835 80
|18 -8
r
1.42765 w
*v
1. 43099 M
'v
1.43645 80
9 o
1. 43972
92
Name and Carbon Skeleton
M. P.,C,
B. P., C.
@ 760mm
X
-s
Additional Data
;r<zn*-l,3-Dimethyl~
cycloheiane
-79.4 )
120.59 to
0.762 M
1.4176 M
121.59"
0.76628 80
1.4254 121
1 20.40 80
0.7706"
1.4262"
119.5 88
0.772 >
1.42470^
119 1 "
0.78251 M
1. 42265 23
119"
H H
@ 756mm
a
1. 43030
"5,
1. 43493 23
1. 42480 23
M 20
1.41772 80
*r
1. 42099 80
n !8.8
r
1. 42047 80
*y
1. 42376 80
'y
1. 42919 80
?/ 26.4
*(?
1. 43254
93
Name and Carbon Skeleton
M. P.,C
B. P., C.
760mm
Of
g
Additional Data
1,3-Dimethyl-
cyclohexane
121.6 24>3te
0.7208 2
1.4218 181
121.3 to
81
26
121.5 32
0.7661 1W
1.4230 1
121.2 to
26
25
121.8 17
0.7661 M
1.4288 48
121 to 123 m
25.4
22.5
121 to
0.7672 26
1.4239 1 ' 2
121.5 lif
25.4
22
121 12
0.773 *
1. 42398 6
120.9 to
25
22
122.5 ll8
0.7671
1. 42499
120.8 166
24
20.75
120 to 121 167
0.7701
1.4234 169
120 6 ' 11J ' 1&9
21.8
1. 42407 22 - 8
119tol23 118
119 to
120 128 - m
0.7707 6
20.75
0.7677 .
1.4246' 66
1.42470 124
1.425 3
1193,124
0.7687
1.4253 8
118 to 120
0.7697 187
[24,
118 10
0.771
1.4255| 8te
117 to 120 1M
0.7712 " 6
k
119.5 m
0.772 24
1.4270 M
75 1mm
0.7723 "-a*
18
118.5 to 119
747mm
0.7822 122
0.766 1M
1. 4278 s8
13.5
119.5 to
7} 20
1.4298 127
120.5 22 - 68
0.774
11
740mm
n 20
^20
1.39405 26
w 81
119,5 to
0.7688 167
'*//
a
120 l
D 11
1. 42060 *
739mm
0.7736 60
n 26 - 4
"a
18
1.42127
0.775
H H A
15
1.42157
0.7761 "
0.7772 *
1.42276
1.40113
94
Name and Carbon Skeleton
Mp r
. r. t C-.
B. P., C
@ 760mm
Of
-5
Additional Data
1,3-Dimethyl-
cyclohexane
(Continued)
0.7812 l27
1.42817 28
0.784 JM
1. 42887 M
0.7874 n2
n *l
@0
1. 42940 6
0.7869 1M
n 'p
rt
1. 43047 B
1. 40528 26
n jf
7
1. 43259 25
9725.4
w #
7
1. 43338 25
7
1. 43394 5
n 22.0
7
1. 43500 6
7
95
Name and Carbon Skeleton
Jf. P.,C.
B. P., C.
@ 760mm
DP
-s
Additional Data
cts-l,4-Dimethyl-
cyclohexane
c
-84 to
124.59
0.7671 23
1. 42300 124
-85 14
123.7 u
0.773 124
1.4257 7
-91.6 80
123.4 14
0.7759 167
1. 42064
121.5 to
0.78271 80
8
c
122 lfl7
0.781 "
1.42833
121.5 I24
15
w 20
120.5 2S
@ 755mm
0.795 J4
1.43299"
w 2 }
0.7952 18
15
1. 42270 23
0. 79925 80
n S
@o
1. 42425 M
0.8075 18
w S; 4 r
1. 42755 M
1. 42700 M
*v
1. 43029 M
W ^- 8 tf
1. 43568 80
(7
1.4391 7 80
n !8.8
**;
96
Name and Carbon Skeleton
M. P.,C.
n o/-
Z5. P. t C.
760mm
Of
s
Additional Data
trans-1 ,4-Dimethyl-
cyclohexane
-33.34
1 19.63 M
0.7620 M
1. 42095 IM
134
119.5 184
@22
1.4224" 7
-37.2 M
120.07 to
0.7672
1.4248"
120.67
@20.5
1.41833
120 to 121 '
0.76264 M
n 20
119.0 to
0.7638 "
a
119.5"
0.7655 "
1.41914"
119"
0.7688
W// .
118.6 to
0.769 124
1.42578"
@ 728mm
0.77913
1,42686"
w /?
1.43046"
n 20
7
1.43163 23
7
1.42000"
1.42120"
n /J
1. 41566 w
n Ht
T
1. 41887 80
r
1.41827 80
*
1.42160 80
*v
1.42697 80
*r
1.43033
^*a
97
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
i."
Additional Data
1,4-Dimethyl- .
cyclohexane
-32 to
120 to 120.2
0.7620 27
.4224 I62
-33 7
@ 768mm 27
@22.2
.42326 8
-59"
122.7 to 123 17
0.7669
.4240 3
122.0 to
0.7690 "'
.4244 18
124.0 118
0.7727 24 - 30a
.4253 ". 30
121. 7 *<
0.777 118
.4271 118
120.5 to
n ao
^20
.42597 3
121 I62
0.7722 8
@15.7
120 l ' 2
15.7
1.4299 '27
119.5 to
0.7767 2< - 30ft
@ 11
120.5 3 - 127
@15
1.41835 27
119.5 to
0.783 17
w^
120 189
@ 15
a
1 19 106
0.7819 127
1. 42407 3
119.5tb
@ 11
a
120 M
0.7866 112
1 .42592 27
@ 740mm
<o>/0
H "
0.7861 l06
1. 43174 3
rt
%
1. 43035 27
7
1 .43624 3
n a
98
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
7/<
Additional Data
Propylcyclohexane
o-o-c
1
-94.5 124
154.7
155,7 24 - 37
155 8
0.7932
0.791 8
@21
1.4371
1.437 8
@21
^ 0.000757/C.
(0 to 20)
154.9 to
0.7898 23
1.4360 24 - 308
155.0 8
0.7929 24,30a
1. 43690
154 to 155
0.7930 M
1.4370
153 to
154 e, ni, 112, 127
140 to 142 188
154.5 to
0.7946 M
9.7971 w
0.793 "
1.4374 M
1.4382"
1.440 8
155.5 23
@ 756mm
153tol54 flfi
@ 753mm
155 to 156 r ' 5
730mm
0.7968 24.3^
@15
0.796 8
0.8025 127
1.4449127
1.4338323
n a
1. 44160 23
0.7819 ' 38
0.8091 2
1.44616 23
n ff
t
1.435922 3
0.8098 "i
Isopropylcyclohexane
c-o-c
- 89,8 12fl
154.7 133
0.787 162
1,4410 12<J
154.5 128
0.7902 23
1.4411" 8
151. 7 to
0.799 18
1.4444 127
153.0 "8
151 to 153 127
Dll
0.8090 l * 7
1.43428"
150 to 153 78
@n
n " a
147 to ISO 162
146 to 148 " 2
152 to 153 * 3
@ 756mm
0.8 1 2 2
1. 44225 23
"*.
1. 44686 23
Hff f
1. 43642 23
99
Name and Carbon Skeleton
Ijf "D /""
M. jr., C.
B. P., C.
@ 760mm
iff
s
Additional Data
l-Methyl-2-ethyl-
cyclohexane
c
| c-c
fY
152.6 to
154.7 8
151 M
0.784 "
0.805 " 8
1.432"
1.4400 118
k^
150 to 152 <
0.7945 84
l-Methyl-3-ethyl-
cyclohezane
c
148.4to
150 8
0.82 13 "
0.791 8
1.431 1 83
1.4344"*
145 to 146 70
D 20
1.460"
\
C-C
0.8320 70
M-Methyl-3-ethyl-
cyclohexane
148 to 149 148
0.7896 " 8
1.4353 "
@ 743mm
@17
17
l-Methyl-4-ethyl-
cyclohexane
c
6
c-c
150.1 to
151 l18
150 2
147 107
0.791 8
0.7884
0.8041 "*
@0
1.4343 118
1.435 1OT
100
Name and Carbon Skeleton
M. P.,C
B. P., C.
760mm
D?
n D
Additional Data
l,M-Trimethyl-
cyclohexane
c c
138.5 to 139 45
0.7866
1. 43385
137 to 138 8 -<>
25.3
25.3
134.8 to
0.7663 <*
1.4327
.
135
0.7703
17
c
15
1.4237*
0.7848
15
15
1.4324
15
1.43177*
1.43998 s
1.44453 3
CI5-1 ,2,3-Trimethyl-
cyclohexane
(Hexahydrohemimellitene)
144 to 146 23
0.7930
1. 43475
@ 755mm
n n
a
C
1 C
1. 44259"
rV
**,
U\
1. 44724 M
^X/^ N,
C
n y
1. 43682 M
101
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
/)!
4
Additional Data
frans-l,2,3-Trimethyl-
cyclohexane
(Two possible trans
142 to 143.5 23
0.7898 166
1.4346 1 "
isomers)
@ 762mm
0.7914
1. 43373 23
141 "
^//
@ 736mm
1.44150 23
3,
1. 44606
*/20
t
cis-l,2,4-Trimethyl-
cyclohexane
( Hexahy dropseudocumcnc)
146 12
0.7850 23
1. 43314 12 <
c
144.8 to
0.790 120 ' 124
1.434 12
1 c
145.8 12
0.7848 "
1. 43120 2S
a
141.5 23 - 27
16.7
s.
1. 43902
\
H **fi
c
1.44361 2a
n 2 ?
7
1.43341 23
102
Name and Carbon Skeleton
Jlf. P.,C
B. P., C.
@ 760mm
D?
*
Additional Data
cyclohexane
138.5 to
0.7813 23
1. 42909 23
139.5 23
n ff
@ 755mm
a
1. 43675 23
n H
1.44135 23
7
1.43121 23
l,2*,4'-Trimethyl-
cyclohexane
142 l2 *
0.786 l24
1.43 209 12
l%2S4'-Trimethyl-
cyclohexane
140 12 <
0.774 l24
1.42916 l24
103
Name and Carbon Skeleton
K/r P r*
M. Jr., C.
B. P., C.
@ 760mm
D?
nS
Additional Data
l,2,4-Trimethyl r
cyclohexane
145 to 146 '
0.7652 74
1.429 30
143 to 144 112
0.7667 M
1.4344 32
142 to 144 m
0.778 30
@13.5
140 30
0.7808 74
1. 43054
138"
0.7807 171
n S' 7
135 to 136 74
18
1.42962
141. 5 to 143 27
0.7850 27
/jlj.8
@ 759mm
143 to 144 27
@ 16.6
0.7812 63
a
1. 43829 27
n"- 7
@ 759mm
@o
/
0.8052 I12
1.43733"
@o
w^.fi
1.44281 27
nj}- 7
1.441 87 27
1 ,2,5-Trimethylcyclo-
hexane
c
140 to 141 3
0.7799 3
1. 43056 3
1 c
@ 16.9
@ 16.9
O/
1. 42860 3
,
n//
c
1. 43632 3
1. 44099 '
8
7
104
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
#
8
Additional Data
cis-1 ,3,5-Trimethyl-
cyclohexane
(Hexahydromesitylene)
140.0 to
0.7765 **
1.42768"
140.5
0.7773 *
H H
C
A
@ 752mm
139.5 to
140.5 "
@ 750mm
1.42808"
8.
1.43536"
C
^^
1.43586"
1.43990"
1.44028"
n 20
7
1.42990"
S fl
1.43010"
105
C,H
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
8
Additional Data
<rc/is-l,3,5-Trimethyl-
cyclohexane
138 to 139
0.7720
1.42506"
@ 761mm
8 m
138.5 to 139 23
@ 754mm
1.42526"
tW
1.43279"
1. 43288 "
1.43725"
7
1.43735"
7
1.42710"
1.42740"
*)20
106
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
Iff
-s
Additional Data
1,3,5-Trimethyl-
cyclohexane
140 to 142
0.7521
1.4304 48
139.3 to
@25.5
@21
141.4 "
0.7590 M
1.4212 M
138 "
0.7666 M
1. 42688 w
137.5 8
0.7711 8
1.4316 118
137 to
0.777 us
1.4320"
139 110.112
D 20
^20
1.42597 3
136 to 140 48
0.7744 27
@15.7
136 to 137 27
15.7
1.42407 3
135 to 137 M
0.7777 3
W B' 7
134 to 136 l
13.1
1.42683"
137 to 139 68
110.
W 16.7
@ 752mm
0.7784 "
112
a
1.43174'
0.781 1 63
1.43460"
@0
W /J' 7
1.43624*
W 15.i
7
1.43916"
n l
y
107
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
Iff
8
Additional Data
Butylcyclohexane
179
0.7997
1.4412
*2 ooooissrc
c-c-c-c
1
-78.6 133
177tol78 fls>
0.797
1.440*
^ (10 to 20)
n
@ 763.5mm
180.5 2 .oa
0.7987 M
0.7996 9
1.440 76 B
1.4408 118
~~= - 0.00041 3/C.
(10 to 20)
XX
180.1 to
0.8005 24 - 30a
1.4410 24 ' 30
m9 us
,L
0.8178 21
1.4426 "
178 to 182 2 >
0.799
1.4449 127
177 8
j^20
@11
176.5 to
0.8037 24 ' 30a
178.5 127
(& 15
176 to 177"
0.8078 127
% 7 55mm
68 @ 16mm 8
0.8305 21
rf-2-Cyclohcxylbutane
((/-sec-Butylcyclohexane)
176 to 178
0.805
1.4460 89
WS-+0.4S
17460
@27
63 @ 15mm 60
0.810
0.81559
D Z()
2-Cyclohexylbutane
( sec-B utylcyclohexane)
78.5 to
0.811 118
.4458 n8
OOC-C
179.5 "8
D%
.4487 l27
1
77.2 33
0.8156 I27
@11
72 to
174.5 127
@ir
C 10 HI
108
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
Iff
u
Additional Data
2-MethyH-cyclo-
hexylpropane
(0-Butylcyclohexane)
1 70.8 to
0.7950 23
1.4391 118
C
1
c~c-c
1
171.7 118
169 21
@ 754mm
0.797 " 8
D 20
1.43686"
"B.
1.44467 23
o
1. 44920 3
-B,
1.43904"
2-Methyl-2-cyclo-
hexylpropane
(^/-Butylcyclohexane)
169.9 to
0.813 ll8
1.4464 " 8
C
1
C-C-C
171.4
167 to 169 127
166 to 167
n 80
i/ao
0.8305 85
1. 45562
1
0.8205 127
11
11
l-Methyl-2-propyl-
cyclohexane
c
1 c-c-c
a
175.2 to
177.0"*
171 to 172.5 6
175.5 to 176 6
@ 755.5mm
0.8064
0.810 " 8
D ao
0.8130 "
1.44378"
1.4445" 8
1.4468"
56 13mm 64
109
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
M 20
H D
Additional Data
l-Methyl-2-isopropyl-
cyclohexane
(o-Hexahydrocymene)
171 1W
0.8134 109
1.447109
Dl l
21
C
c 1
0.8326 IM
I oc
Dl
a
d-l-Methyl-2-iso-
propylcyclohexane
169 to 170"
0.8297 1<9
1.45649"'
W^^+14.9 ^
@ 752mm
1 -Methyl-3-propyl-
cyclohexane
c
I
171.1 to
0.7895 lfl1
1.4352 164
0,
173.0 118
169 to 170 164
164 to 165 70
@21
0.796 118
DZ
@21
1.4377 J18
c-c-c
C,,H
110
Name and Carbon Skeleton
M. P.,C,
B. P., C.
@ 760mm
D?
Additional Data
l-Methyl-3-isopropyl-
cyclohexane
(w-Hexahydrocymene)
166 to 168 ll1
0.7965 1W
1.440 IW
166 to 167""
@24
@24
C
t
167 to 168 *
0.8033 Ul
1. 44204
a.
@ 756mm
c-c
1
1
C
d-l-Methyl-3-iso-
propylcyclohexane
[]= 4-0.45
167 to 168 109
0.7948 44
1.446 109
168 to 168.5 44
z>5
23
@ 758mm
0.8235 1M
1.4380 "
Dl
M-Methyl-3-iso-
_ 02g047
propylcyclohexane
167.5 to 168 <
0.7938 47
1.4358 4?
@ 749mm
P20
0.8078
Ill
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D?
-8
Additional Data
l-Methyl-4-propyl-
cyclohexane
c
168 to 169 9
0.7941 M
1. 43884 9
1
@ 765mm
0.798 118
1.4393 118
r-S
174.3 to
Dll
U
177.1 118
I
c-c-c
cw-l-Methyl-4-iso-
propylcyclohexane
(/>-Hexahydrocymene)
168.5 124
0.816 124
1.45149 l24
C
1
r^i
y
c-c-c
propylcyclohexane
161.0 124
0.792 l84
1.43931 l24
112
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
Iff
-B
Additional Data
l-Methyl-4-isopropyl-
cyclohexane
171 to 172"
0.7448 25
1.4370 1
171 26
@79.2
25
170tol72 m
0.8061
1,440109
170 82
@25
@25
169 to 171 M
0.8020 1M
1.4375 4fl
169 to 1 70.5 7
Dj 1
1.43757"
169 to 1 70 2
0.7904
1.4380 i 26
169 141
1 43840\
0.790 M
j 68
168 to 170 ua
0.7930 63
1.4385*
168tol69"
0.7960 22 ' 68
1.44187 "
167 to 168 109
0.7963
1. 40789 25
166 to 168 111
0.7974 m
w 7 }- 2
165 to 169 M
*
J7| 40
0.7990 8
1.43418
@, 759mm
0.8039 " 9
n H
a
169 l
0.7904 2S
1.43458"
@ 758mm
C) 19.9
n%*
169.5 to 170"
@ 754mm
0.8060
@17.5
1.41521 26
W S' 2
169 168
0.796 7
@ 752mm
rt!
1.44196"
169" 8
0.803 141
n *l
@ 747mm
rt!
1.44234"
166tol68 22 - 8
0.8056 M
H H' 9
@ 746mm
1.41954"
63 @ 22mm >
0.8132 2
*y
0.81 79
1.44651
(olO
W S' 1
\OJ U
y
0.8066
1.44694"
0.8067
7
0.8134 1W
D?
113
Name and Carbon Skeleton
M. P,,C
@ 760mm
Iff
nj
Additional Data
1 ,3-Diethylcyciohexane
c-c
173.5 to
0.7957 " 2
1.4388 172
1
174.5 l18
@22
1.4409 1 "
169 to 173 127
0.800 118
1.4449 w
N
169 to 171 172
r> 20
1/20
^11
C-C
0.81 18 m
1 ,4-Diethy iuy lauaexafle
C-C
1 74.6 to
0.802 " 8
1.4415 l18
A
176.4 '
^20
C-C
l,3-Dimethyl-5-ethyl-
cyclohexane
c
168.5 to
0.7929 l29
170 I2e
^20
168 to 170
0.796 10
\
Pi!
C-C C
0.8073 12B
0.8076 10
doll 2<
114
Name and Carbon Skeleton
MP r
i * > \*
B. P., C.
@ 760mm
Iff
*
Additional Data
1,2,3,4-Tetramethyl-
cyclohexane
(Hexahydroprehnitene)
84 @ 5mm 81
0.8219 "
1.4531
C
rV
V^
1 c
C
cis-l,2,3,5-Tetra-
methylcyclohexane
(Hexahydroisodurene)
168 to 1 70 23
0.8166 M
1.44621 M
@ 762mm
tt /J
C
a
1 c
1.45472 M
CY
"B.
AA
1.45963
C C
^AT
7
1.44847*
n so
fran$-l,2,3,5-Tetra-
methylcyclohexane
(Several possible trans
isomers)
162 to 164
@ 765mm
0.8140
1.44440 "
a
1.45212 w
1.45667 *
"5
y
1.44657 "
115
C,,H S ,
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
*5
Additional Data
cz*s-l,2,4,5-Tetra-
methylcyclohexane
(Hexahydrodurene)
171
0.8122 * 3
1.44420"
@ 755mm
5
C
a
1 c
1.45252"
fj
1.4575(5"
c I
n s
c
1.44647 M
frans-l,2,4,5-Tetra-
methylcyclohexane
(Several possible trans
isomers)
166 to 168
0.8100 23
1.44230"
-s.
1.45003"
1.45470
7
1.44446"
116
Name and Carbon Skeleton
M. P.C.
B. P., C.
@ 760mm
DT
ng
Additional Data
1 ,2,4,5-Tetramethyl-
cyclohexane
160.5 to
0.7578 M ' M
1.4299 - 8
161. 5 3
@70
40
160 to
0.7765 92
1.4196 M
161.5 22 - M
@23
@23
755mm
172 to 174 w
0.7934
0.81 1 1 "
1.43717J*'
730mm
0.7910 8
1.44511 >
169 to
@ 13.1
1.43718 8
170.$
0.825 1H
13.1
@ 711mm
@o
1.44260 1M
n 20
1.435173
n\
1.45064 1C1
1. 44307
ngjj
1.4SS24" 1
Y
1. 44772 8
y
Pentylcyclohexane
C-(C)j-C
20 1.4 to
0.802 8
1.4428 118
201.9 118
0.8044
1.444 8
199*
0.804 8
1. 44428 M
194.5 to
DS
1.454 88
198
0.823
16
191 to 192
16
1.4466 m
197 to 199 M
0.8160 127
11
754mm
11
84 to 85 8
@ 16mm
117
Name and Carbon Skeleton
Af. P. t C
B. P., C.
@ 760mm
DT
nU
Additional Data
/-2-Cyclohexylpentane
WB-o.81-
c-c-c-c-c
101
0,814 M
6
@18mm
88 "
@15mm
@27
0.823 M
cf-2-Methyl-l-cyclo-
hexylbutane
(<M2-Methylbutyl]-
191 si
0.805
cyclohexane)
@25
C
1
c~ooc
6
3-Methyl-l-cyclo-
hexylbutane
c
192.5 to 193 M
0.8023
1,4420 l "
1
c-c-c-c
@ 774mm
0.8235
1.44233 *
1
193.8 to
0.800 8
1.58125 M
195.2 ll8
D 20
1.4477 127
1 1
190 to 194
0.8136
@n
190 to 191 w
118
Name and Carbon Skeleton
M. P.,C.
B. P., C
@ 760mm
Iff
ng
Additional Data
2-Methyl-2-cyclo-
hexylbutane
c
1
193.3 to
0.821 "
1.4510
o-oo-c
195.2 "
Dll
1.4538"'" 8
6
191 to 192 36
0.8226
2,2-Dimethyi-l-cyclo-
*-** -0.0007 7 /C.
hexylpropane
(20 to 40)
c
0.78352 94
1.4416 94
-^=-0.00043/C.
1
c-c-c
@40
1.4502 94
1 (-30 to +20
1 1
0.79893 *
@0
JL
1.4631 M
O
-30
l-Methyl-2-butyl-
cyclohexane
c
195.6 to
0.813 8
1.4467 8
| c-oc-c
a
198.1 l18
119
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
DT
-g
Additional Data
l-Methyl-3-butyi-
cyclohexane
c
i
194.8 to
0.801
1.4418 118
0,
195.2
Pi!
oc-oc
l-Methyl-4-butyl-
cyclohexane
c
1
195.9 to
0.807 8
1.4441 118
O
196.6
PS
1
c-c-c-c
Pentamethyl-
cyclohexane
c
6_
180 to 185 m
0.7990 M
1.43848"
/ c
'
183 to 186 M
@50
@50
@ 752mm
0.8200
1. 44995 w
. , \
0.8081 127
1.4455 m
c | c
11
11
c
120
Name and Carbon Skeleton
TUI p r
jxi. t, t L*.
B. P., C.
@ 760mm
iff
-I
Additional Data
Hexylcyclohexane
C-(C) 4 -C
221 8
0.8239 M
1.446 8
A,
219 to 221
0.806 8
1.45222 M
f]
102 8
k/ 1
(o^ 1 6mm
/-2-Cyclohexylhexane
[]-- 0.90 '
c-c-c-o-c-c
6
101
@ 18mm
0.823
cf-3-Cyclohexylhexane
[<*]= +0.57
c-oc-oc-c
6
111 60
^/) 28mm
0.823
2-Methyl-2-cyclo-
hexylpentane
c
206 to 207 35
0.8372
1.4670 35
16
c-oc-c-c
1
O
121
Name and Carbon Skeleton
Kjf p r
1VL. JT. t C-.
B. P., C.
@ 760mm
D?
ng
Additional Data
M-Methyl-1-cyclo-
Hg 1.68^
hexylpentane
c-c-c-c-c
110 2
0.806 2
1 1
@ 15mm
@27
O
3-Methyl-3-cyclo-
hexylpentane
c
207 to 208 38
0.831036
1.4574 36
1
@ 16
@16
c-c-c-c-c
1
O
l-Methyl-2-pentyl-
cyclohexane
c
215.8 to
0.816 " 8
1.4487 118
| O(C) 3 -C
219.1 118
D 90
a
1*4
122
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
tif
-8
Additional Data
l-Methyl-2-(3-methyl-
butyl)-cyclohexane
c
1 c-c-c-c
O/ \
c
204 M
0.812 M
17
0.825 M
1.454 M
17
l-Methyl-3-(3-methyl-
butyl)-cyclohexane
c
A
205
CX
c-c-c-c
1
1
c
l,3-Dimethyl-5-(2-
methylpropyl)-cyclo-
hexane
c
|
193 to 195 "
0.8227
/O,
c-c-c c
c
123
CliH.24
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
/>;
s
Additional Data
l-Methyl-3-ethyH-
isopropylcyclohexane
Ma-- 12.25"
c
207 to 208
0.8159
1
@ 736mm
0.8275 w
@0
. \
| c-c
c-c-c
1,3,4-Trimethyl-
1-isopropylcyclohexane
c
i
177
0.8375 28
1.4636"
1
c c-c
\/
^
ON
\ c
c
l,2-Dimethyl-3,6-
diethylcyclohexane
1
c
c-c 1 c
YY
91 to 92"
@ 4mm
0.8536 81
1. 4673 "
UN
C-C
VII Af 4
124
Name and Carbon Skeleton
TUf T> r
JKL. JT,, C-.
B. P., C.
@ 760mm
Iff
fig
Additional Data
Hexamethyl-
cyclohexane
(Hexahydromell itene)
210to214 22 - M
0.8405 22 - w
1.4606-^
C
C | C
XX
c | c
c
f-3-Cyclohexyl-
[]-- 0.68
heptane
o-c-c-c-c-c-c
112"
0.819
6
@ 15mm
@25
4-Cyclohexylheptane
c-c-c-c-c-oc
228 *-'
6
125
C i 3
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
w 20
n D
Additional Data
3-Methyl-3-cyclo-
hexylhexane
c
224 to 226 Sft
0.8406
1.4646 36
1
@16
16
c-c-c-c-c-c
I
o
3-Ethyl-3-cyclo-
hexylpentane
c c
222 to 223 35
0.8388 36
1.4658 35
1
@ 16
@16
c-c-c-c-c
6
2,4-Dimethyl-2-cyclo-
hexylpentane
c c
220 to 221
0.8304 M
1.4580"
1 1
@16
@16
c-c-c-c-c
1
O
126
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
iff
s
Additional Data
l,lf3-Trimethyl-2-
butylcyclohexane
c c
94 to 95 "
0.8292 1(u
1.4563 101
\y oc-c-c
S^^S
@ 10mm
@19
@19
c
CM Hog
Octylcyclohexane
C-(C)f-C
117 to 119
0.8150
1. 45070
O
llmrn
I-4-Cyclohexyloctane
c-o-c-c-c-c-c-c
123 M
0.823 M
O
@ 15mm
@27
127
Name and Carbon Skeleton
M. P.,C
B. P., C.
760mm
D?
ng
Additional Data
4-Methyl-4-cyclo r
hexylheptane
c
115 to 116 "
0.8483 6
1.4717 36
1
c-c-c-c-c-c- c
13mm
@19
19
6
3-Ethyl-3-cyclohexyl-
hexane
c-c
114 to 116"
0.8547 w
1.4754 M
1
c-c-c-c-c-c
@ 13mm
19
23
1
o
2,5-Dimethyl-2-cyclo-
hexylhexane
c c
134 to 135
0,8512
1. 4685 w
1 1
c-c-c-c-c-c
@30mm
@19
23
6
128
Name and Carbon Skeleton
M. P.?C.
B. P., C.
@ 760mm
D?
4
Additional Data
4-Bthyl-4-cyclohexyl-
heptane
c c
129 to 130"
0.8376 36
1.4598
I
@ 13mm
@> 19
@ 23
ooooc-oc
6
3,6-Dimethyl-3-cyclo-
hexylheptane
c c
120 to 121 35
0.8717 **
1.4871 3B
1 1
10mm
@ 19
@ 23
ooc-c-ooc
6
3-PropyH-cyclohexyl-
hexane
c-c-c
83 to 85 *
0.8285 "
1.4550"
c-c-c-c-c-c
@ 2mm
1
o
129
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
,r
ng
Additional Data
6-Methyl-2-[4-methyl-
cyclohexyl]-heptane
W8--UU-.M
(Hexahydrozingiberene)
125 103
0.8244 I17
1. 45423 m
@ 15mm
0.8264 114
1.4560" 4
C-C-C-C-C-C-C
| |
128 to 130 114
0.829 104
1.4567 104
Oc
@ llmm
0.828 l03
123 to 125 m
@15
@8mm
c
l-Methyl-4-isopropyl-
2-(3-methylbutyl)-
cyclohexane
c
131 to 133 n
0.8250
1. 45562 1)fi
| c-c-c-c
ai
@ 14mm
22
@22
i
c
1
c-c-c
4-Propyl-4-cyclohexyl-
heptane
c-c-c
133 to 135 * 6
0.8382 35
1.4606 26
1
@, llmm
@ 19
@23
c-c-c-c-c-c-c
1
o
130
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
iff
8
Additional Data
2,4,6-Trimethyl-4-
cyclohexylheptane
c c c
133 to 135 36
0.8396 *'
1.4622
1 1 1
c-c~c-c-c-c-c
@ llmm
@19
@23
1
o
C 17 Il84
3-Butyl-l-cyclohexyl-
heptane
c-oc-c
95 to 96 M
0.8351 87
1.4648 87
1
c-c-c-c-c-c-c
@ 2mm
1
o
2-Methyl-4-propyl-4-
cyclohexylheptane
c c-c-c
148 to 150
0.8441
1.4658"
1 1
c-c-c-c-c-c-c
@ 10mm
@19
@23
1
o
131
Name and Carbon Skeleton
Mp /" 1
. Jr., C.
B. P., C.
@ 760mm
tif
^
Additional Data
2,5,8-Trimethyl-5-
cyclohexylnonane
c c c
1 1 1
c-c-c-c-c-c-c-c-c
156 to 158 2 *
@ 12mm
0.8440 36
@ 20.5
1.4666 s *
o
C 19 lias
2,8-Dimethyl-5-ethyl-
5-cyclohexylnonane
c
162 to 164 86
0.8681 "
1.4789 35
1
c c c
1 1 1
c-c-c-c-c-c-c-c-c
6
@ 10mm
@ 20.5
CTT
20<El 4 o
2 ,8-Dimethyl-5-propyl-
5-cyclohexylnonane
c
190 to 192 * 6
0.8421 8
1.4646"
1
c
1
@ 17mm
@ 20.5
1
c c c
1 1 1
c-c-c-c-c-c-c-c-c
6
C.H,
132
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D;
g
Additional Data
l-(4-Methylpentyl)-4-
(1,5-Klimethylheiyl)-
cyclohexane
c
83 to 186 *
0.8331 6
1.46001 l16
1
@ 14mm
o-c-c-oc
rS
LJ
c-oc-c-c-c-c
1
c
Cfti H-42
Pentadecylcyclohexane
e-(Chr-C
25 M
178"
0.8323 3 <
1.4612 34
6
@ 0.7mm
@ 19.5
2,8-Dimethyl-S-iso-
butyl-S-cycloheacyl-
nonane
ooc
162 to 163
0.8797 3
1.4905"
1
@ 6mm
@ 20.5
c c c
1 1 1
C.-C-C-O-C-C-OC-C
1
133
Name and Carbon Skeleton
M.P.,'C.
B. P., C.
@ 760mm
iff
n 20
Additional Data
Octadecylcyclohexaae
6"
4L20to
41.45
128
40 ."
35 l39
207.5 to
208.5
@3mm
0.834 7
@25
1.4538 76
@25
Cyclohexyldocosane
C-(C)rC
6
49 to
50 7fl
0.8327 7
1.4643 7
5-Cyclohexyldocosane
C-C-C-C-C-(C)iff-C
6
0.8395 7
@25
1.4627 7 '
25
CTT
3'/XX(j4
5-Cyclohexylhexa-
cosane
OC-C-C-CMQw-C
6
30 to
31
0.8372 7
@25
1.4677 7
@25
134
(1) R. Adams and J. R. Marshall, J. Am. Chem. Soc. 50, 1970, 1928.
(2) M. Amouroux and M. Murat, Compt. rend. 154, 992, 1912.
(3) K, v. Auwers, Ann. 420, 84, 1920.
(4) K. v, Auwers and F. Eisenlohr, Z. physik. Chem. 83, 429, 1913.
(5) K. v. Auwers, R. Hinterseber, and W. Treppman, Ann. 410, 257, 1915.
(6) L. Balbiano and L. Angeloni, Atti accad. Lincei Roma [5] 13B, 142, 1904.
(7) A. Berkenheim, Ber. 25, 686, 1892.
(8) M. Bourguel, Bull. soc. chim. [4] 41, 1475, 1927.
(9) G. Broughton, Trans. Faraday Soc. 30, 369, 1934.
(10) J. H. Brown, H. W. Durand, and C. S. Marvel, J. Am, Chem. Soc. 58, 1594, 1936.
(11) J. W. Bruhl, Ber. 27, 1065, 1894.
(12) J. H. Bruun and M. M. Hicks-Bruun, J. Research Nat. Bur. Standards, 7, 607, 1931.
(13) E. Carter and D. Jones, Trans. Faraday Soc. 30, 1027, 1934.
(14) G. Chavanne and P. Becker, Bull. soc. chim. Belg. 31, 95, 1922.
(15) G. Chavanne, M. O. Miller, and Cornet, Bull, soc. chim. Belg. 40, 673, 1931.
(16) G. Chavanne and L. J. Simon, Compt. rend. 168, 1111, 1919.
(17) G. Chavanne and L. J. Simon, Compt. rend. 168, 1324, 1919.
(18) G. Chavanne and H. Van Risseghem, Bull. soc. chim. Belg. 31, 87, 1922.
(19) A. Crossley and N. Renouf, J. Chem. Soc. 87, 1487, 1905.
(20) G. De>rdin, Ann. phys. [9] 11, 253, 1919.
(21) R. Douris, Compt. rend. 157, 55, 1913.
(22) M. K. Dyakova, A. V. Lozovoij, and T. G. Stepantseva, J. Gen. Chem. (U.S.S.R.) 7, 722, 1937.
(23) F. Eisenlohr and G. Gorr, Fortschr. Chem. Physik, 18, No. 9, 10, 1925.
(24) E. B. Evans, J. Inst. Petr. Tech. 24, 321, 1938.
(25) J. F. Eykman, Chem. Weekblad, 3, 685, 1906.
(26) J. F. Eykman, Chem. Weekblad, 6, 699, 1909.
(27) J. F. Eykman, Chem. Weekblad, 8, 651, 1911.
(28) E. H. Farmer and R. C. Pitkethly, J. Chem. Soc. 1938, 11.
(29) E. C. Fortey, J. Chem. Soc. 73, 932, 1898.
(30) D, Gadaskin and S. Ssorkina, Chem. Z. 37, 725, 1913.
(30a) F. H. Garner and E. B. Evans, J. Inst. Petr. Tech. 18, 751, 1932.
(31) J. W. Gifford and T. M. Lowry, Proc. Roy. Soc. London, A104, 430, 1923.
(32) M. Godchot, Bull. soc. chim, [5] 1, 1153, 1934.
(33) D. C. Jones and S. Amstell, J. Chem. Soc. 1930, 1316.
(34) A. J. Haagen-Smit, Koninkl. Akad. Wetenschappen Amsterdam, 34, 165, 1931.
(35) O. Halse, J. prakt. Chem. 92, 40, 1915.
(36) D. C. Hibbit and R. P. Linstead, J. Chem. Soc. 1936, 470.
(37) W. Huckel, K.Kumetat, and H. Severin, Ann. 518, 184, 1935.
(38) I. Kagehira, B.ull. Sdc. Chem. Japan, 6, 241, 1931.
(39) W. Kay and W. Perkin, J. Chem. Soc. 87, 1079, 1905.
(40) F. S. Kipping and W, Perkin, J. Chem. Soc. 57, 25, 1890.
(41) N. Kishner, J. prakt. Chem. [2] 56, 364, 1897,
(42) N. Kishner, J. Russ. Phys. Chem. Soc. 40, 676, 1007, 1908.
(43) N. Kishner, J. Russ. Phys. Chem. Soc. 43, 582, 1911.
(44) N. Kishner, J. Russ. Phys. Chem. Soc. 43, 1562, 1911.
(45) N. Kishner, J. Russ. Phys. Chem. Soc. 44, 854, 1912.
(46) N. Kishrier, J. Russ.,Phys. Chem. Soc, 44, 1754, 1912.
(47) N. Kishner arid Sawadosky, J. Russ, Phys. Chem. Soc. 43, 1132, 1911.
(48) Klepper, Chim et Ind. Spec. No. 261, 1929.
(49) E. Knoeveriagel and C. Fischer, Ann. 297, 185, 1897,
(50) E. Knoevenagel and MacGarvey, Ann. 297, 160, 1897.
(51) E. Knoevenagel and J. Tubben, Ann. 297, 150, 1897.
(52) E. Knoevenagel and G. Wiedermann, Ann. 297, 169, 1897.
135
(53) M. Konowalow, J. Russ. Phys. Chem. Soc. IP, 255, 1887.
(54) R. Kuhn and A. Deutsch, Ber. 65, 43, 1932.
(55) D. Kursanoff, J. Russ. Phys. Chem. 31, 161, 1899.
(56) D. Kursanoff, J. Riiss. Phys. ciiem. 33, 301, 1901.
(57) S. Lebedev and F. Skawronskaja, J. Russ. Phys. Chem. Soc. 43, 1126, 1911.
(58) R. Lespieau and R. L. Wakeman, Compt. rend. 192, 1395, 1931.
(59) P. A. Levene and S. A. Harris, J. Biol. Chem. 112, 195, 1935.
(60) P. A. Levene and R. E. Marker, J. Biol. Chem. 97, 563, 1932.
(61) P. A. Levene and R. E. Marker, J. Biol. Chem. 110, 299, 1935.
(62) P. A. Levene and R. E. Marker, J. Biol. Chem. 110, 311, 1935.
(63) R. Y. Levina, D. A. Petrov, and D. M. Trakhtenberg, J, Gen. Chem. (U.S.S.R.) 6, 1496, 1936.
(64) R, Y. Levina and A. A. Potopova, J. Gen. Chem (U.S.S.R.) 7, 353, 1937.
(65) R. Y. Levina and D. M. Trakhtenberg, J. Gen. Chem (U.S.S.R.) 6, 764, 1936.
(66) R. Y. Levina and Tzurikov, J. Gen. Chem (U.S.S.R.) 4, 1250, 1934.
(67) T. M. Lowry and C. B. Allsopp, Proc. Roy. Soc. 133A, 26, 1931.
(68) A. W. Lozovoij, M. K. Dyakova, and T. G. Stepantseva, J. Gen. Chem. (U.S.S.R.) 7, 1119, 1937.
(69) A. W. Lozovoij, M. K. Dyakova, and T. G. Stepantseva, J. Gen. Chem. (U.S.S.R.) 9, 540, 1939.
(70) A. Mailhe and M. Murat, Bull. soc. chim. [4] 7, 1083, 1910.
(71) E. I. Margolis, Ber. 69, 1710, 1936.
(72) W. Markownikow, Ann. 302, 1, 1898.
(73) W. Markownikow, J. Russ. Phys. Chem. Soc. 35, 1033, 1903.
(74) W. Markownikow and Oglobin, J. Russ. Phys. Chem. Soc. 15, 331, 1883.
(75) K. Matsubara and W. Perkin, J. Chem. Soc. 87, 661, 1905.
(76) L. A. Mikeska, Ind. Eng. Chem. 28, 970, 1936.
(77) L. A. Mikeska, C. P. Smith, and E. Lieber, J. Org. Chem. 2, 499, 1938.
(78) M. O. Miller, Bull. soc. chim. Belg. 41, 217, 1932.
(79) M. O. Miller, Bull. soc. chim. Belg. 42, 238, 1933.
(80) M. O. Miller, Bull. soc. chim. Belg. 44, 513, 1935.
(81) D. T. Mitchell and C. S. Marvel, J. Am. Chem. Soc. 55, 4276, 1933.
(82) M. J. Montgolfier, Ann. chim [5] 19, 145, 1880.
(83) M. Mousseron and R. Granger, Compt. rend. 207, 366, 1938.
(84) M. Murat, Ann. chim. phys. [8] 16, 108, 1909.
(85) N. Nagornow and L. Rotinjanz, Ann. de d'instut d'analyse physio-chimique 2, 371, 1924.
(86) C. D. Nenitzescu and E. Cioranescu, Ber. 69, 1820, 1936.
(87) G. A. Nesty and C. S. Marvel, J, Am. Chem. Soc. 59, 2662, 1937.
(88) G. S. Parks and H. M. Huffman, Ind. Eng. Chem. 23, 1138, 1931.
(89) P. V. Pauchkov and A. F. Nikolaeva, J. Gen. Chem. (U.S.S.R.) 8, 1153, 1938.
(90) D. Pavlov, J. Russ. Phys. Chem. Soc. 58, 1302, 1926.
(91) W. H. Perkin, Jr. and S. S. Pickles, J. Chem. Soc. 87, 639, 1905.
(92) A. Pictet and M. Bouvier, Ber. 46, 3342, 1913; Compt, rend. 157, 1438, 1913.
(93) A. Pictet and M. Bouvier, Ber. 48, 926, 1915.
(94) H. Pines and R. W. Moehl, Unpublished data.
(95) Renard, Ann. chim. [6] 1, 223, 1884.
(96) F. Richter, W. Wolff, and W. Presting, Ber. 64, 87, 1931.
(97) F. Rose, Jr. and J. White, J. Research Nat. Bur. Standards, 15, 151, 1935.
(98) L. Rotinjanz and N. Nagornow, Z. phys. Chem. 169A, 20, 1934.
(99) D. Rozenthal, Bull. soc. chim. Belg. 45, 585, 1936.
(100) W. Rudewitsch, J. Russ. Phys. Chem. Soc. 30, 587, 603, 1898.
(101) L. Ruzicka and C. F. Seidel, Helv. Chim. Acta, 19, 424, 1936.
(102) L. Ruzicka, M. Stoll, H. W. Huyser, and H. A. Boekenoogen, Helv. Chim. Acta, 13, 1152, 1930.
(103) L. Ruzicka and A. G. Van Veen, Ann. 468, 133, 1929.
(104) L. Ruzicka and A. G. Van Veen, Ann. 468, 143, 1929.
(105) P. Sabatier and A. Mailhe, Compt. rend, 137, 240, 1903; Bull. soc. chim. [3] 29, 974, 1903.
136.
(106) P. Sabatier and A. Mailhe, Compt. rend. 141, 20, 1905.
(107) P. Sabatier and A. Mailhe, Compt. rend. 142, 438, 1906.
(108) P. Sabatier and M. Murat, Ann. chim. [9] 4, 253, 1915.
(109) P. Sabatier and M. Murat, Compt. rend. 156, 184, 1913; Ann. Chim. [9] 4, 274, 1915.
(110) P. Sabatier and J. B. Senderens, Ann. chim. [8] 4, 365, 1906.
(111) P. Sabatier and J. B. Senderens, Compt. rend. 132, 506, 1901.
(112) P. Sabatier and J. B. Senderens, Compt. rend. 132, 1254, 1901.
(113) Schtschukarew, J. Russ. Phys. Chem. Soc. 22, 297, 1890.
(114) F. W. Semmler and A. Becker, Ber. 46, 1814, 1913.
(115) F. W. Semmler and K. G. Jonas, Ber. 47, 2068, 1914.
(116) F. W. Semmler, K. G. Jonas, and P. Roenisch, Ber. 50, 1823, 1917.
(117) F. W. Semmler and I. Rosenberg, Ber. 46, 769, 1913.
(118) F. K. Signaigo and P. L. Cramer, J. Am. Chem. Soc. 55, 3326, 1933.
(119) E. L. Skau, J. Phys. Chem. 37, 609, 1933.
(120) A. Skita, Ber. 53, 1792, 1920.
(121) A.,Skita, Z. angew. Chem. 34, 230, 1921.
(122) A. Skita, A. Ardan, and M. Krauss, Ber. 41, 2938, 1908.
(123) A. Skita and H. Ritter, Ber. 44, 668, 1911.
(124) A. Skita and A. Schneck, Ber. 55, 144, 1922.
(125) V. Smirnow, J. Russ. Phys. Chem. Soc. 41, 1375, 1909.
(126) J. Smittenberg, H. Hoog, and R. A. Henkes, J. Am. Chem. Soc. 60, 1 7, 1938.
(127) R. Stratford, Ann. combustibles liquides 4, 83, 1929.
(128) J. Strating and H. J. Backer, Rec. trav. chim. 55, 903, 1936.
(129) P. Subkow, J. Russ. Phys. Chem. Soc. 25, 383, 1893.
(130) P. Subkow, J. Russ. Phys. Chem. Soc. 33, 711, 1901.
(131) E. Terres and W. Vollmer, Petrol. Z. 31, No. 19, 1, 1935.
(132) J. Timmermans, Bull. soc. chim. Belg. 32, 95, 1923.
(133) J. Timmermans, Bull. soc. chim. Belg. 36, 502, 1927.
(134) J. Timmermans, Comm. Phys. Lab. Univ. Leiden Supp. 64, 3, 1929.
(135) J. Timmermans, H. van der Horst, and H. Kammerlingh-Onnes, Compt. rend. 174, 365, 1922
(136) J. Timmermans and F. Martin, J. chim. phys. 23, 733, 1926.
(137) C. O. Tongberg and M. R. Fenske, Ind. Eng. Chem. 24, 814, 1932.
(138) A. Tschitschibabin, J. Russ. Phys. Chem. Soc. 26, 40, 1894.
(139) P. Van Romburgh, A. G. Van Veen, and A. J. Haagen-Smit, Koninkl. Akad. Wetenschappe
Amsterdam, 33, 589, 690, 1930.
(140) M. G. Vavon, Ann. chim. 1, 144, 1914.
(141) M. G. Vavon, Compt. rend. 149, 997, 1909.
(142) H. Voellmy, Z. phys. Chem. 127, 305, 1927.
(143) A. I. Vogel, Chem. Ind. 57, 541, 1938.
(144) A. I. Vogel, Chem. Ind. 57, 772, 1938.
(145) A. I. Vogel, J. Chem Soc. 1938, 1323.
(146) G. Wagner, Ber. 27, 1636, 1894.
(147) E. Washburn and H. Spencer, J. Am. Chem. Soc. 56, 361, 1934.
(148) J. P. Wilbaut, S. L. Langedijk, J. Smittenberg, and H. Hoog, Chem. Ind. 57, 753, 1938.
(149) H. Weinhaus and P. Schumm, Ann. 439, 20, 1924.
(150) R. Willstatter and J. Bruce, Ber. 40, 3979, 1907.
(151) R. Willstatter and D. Hatt, Ber. 45, 1471, 1912.
(152) R. Willstatter and V. L. King, Ber. 46, 527, 1913.
(153) W. Wolff, Ann. 394, 86, 1912.
(154) F. Wreden, Ann. 187, 153, 1877,
(155) S. Young and E. Fortey, J. Chem. Soc. 75, 873, 1899.
(156) S. Young and E. Fortey, J. Chem. Soc. 77, 372, 1900.
(157) N. D. Zelinsky, Ber, 28, 781, 1895.
137
(158) N. D. Zelinsky, Ber. 30, 387, 1897.
(159) N. D. Zelinsky, Ber. 30, 1532, 1897.
(160) N. D. Zelinsky, Ber. 34, 2799, 1901.
(161) N. D. Zelinsky, Ber. 35, 2677, 1902.
(162) N. D. Zelinsky, Ber. 56, 787, 1923.
(163) N. D. Zelinsky, Ber. 56, 1716, 1923.
(164) N. D. Zelinsky, Private Communication, Beilstein Suppl. Vol. V, p. 20.
(165) N. D. Zelinsky and Dworshantschik, J. Russ. Phys. Chem. Soc. 35, 563, 1903.
(166) N. D. Zelinsky and W. L. Lepeschin, J. Russ. Phys, Chem. Soc. 45, 613, 1913.
(167) N. D. Zelinsky and E. I. Margolis, Ber. 65, 1613, 1932.
(168) N. D. Zelinsky and A. Moser, Ber. 35, 2684, 1902.
(169) N. D. Zelinsky and S. Noumow, Ber. 31, 3206, 1898.
(170) N. D. Zelinsky, K. Packendorff, and E. Chochlowa, Ber. 68, 98, 1935.
(171) N. D. Zelinsky and A. Reformatzky, Ber. 29, 214, 1896.
(172) N. D. Zelinsky and W. Rudewitsch, Ber. 28, 1341, 1895.
(173) N. D. Zelinsky and M. B. Turova-Pollak., J. Gen. Chem. (U.S.S.R.) 2, 666, 1932.
138
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
8
Additional Data
Cycloheptane
0.8100
1.4436 5
^-0.000897,/'C.
O
-13 10
-12 to
-13 12
117 to 117.5*
@ 763mm
119 to 120 2
0.7733
0.7905 "
1.4419
@24
1.44521 12
dt (0 to 60)
^-~0.000444o/C.
(10 to 25)
118 to 120 7
@41.0
1.4440 7 ' 8
117 to 117.3 6
0.8079 9
1.44355
117.5 to 118 ll
@24
1.4466 1 - 2
@ 758mm
0.8118 8
@13.5
116toll8 9
0.811 10
1. 44090
@ 730mm
0.8108 12
W S S
118 12
0.8099 7
1. 44906 "
@ 726mm
0.8098
H .
0.8093 4
/I
1. 45288 ll
Do
M 20
n n
0.816 *
V
7) 15
0.8136 1 ' 2
D 13.B
A/13.5
0.8275 12
0.8253 *
CgXlie
Methylcycloheptane
134
1.4403
~=-0.00047/C.
dt (10 to 20)
c
135 to 136*
0.8052
1.4410 9
1
@ 767mm
0.7981 l3
1.4382 13
O
134 18
133 to 135
0.8087 *
1.4390 13
n 11 -*
#18.5
1.4436 2
139
C.H.,
Name and Carbon Skeleton
M. P.,C.
B. P, C.
@ 760mm
Iff
B
Additional Data
Ethylcycloheptane
c-c
163 to 163.5
0.8152
(^ 740mm
D 20
0.8299
Dl
1 ,2-Dimethylcyclo-
heptane
9 c
153 s
CiflH.20
Propylcycloheptane
c-c-c
6
183 to 184 "
@ 756mm
0.8175 "
1.4502"
1 ,1 ,2-Trimethylcyclo-
heptane
C C r
&
104 to 105 ft
@ 100mm
0.8243 9
1.4527 B
140
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
Iff
s
Additional Data
1 , 1 ,4-Trimethylcyclo-
heptane
c c
6
162 to 163 o
@ 720mm
0.8011 9
1.4420
\
C
(1) M. Godchot, Bull soc. chim. [5] 1, 1153, 1934.
(2) M. Godchot and G. Cauquil, Compt. rend. 191, 1326, 1930.
(3) F. Kipping and W. Perkin, J. Chem. Soc, 59, 214, 1891.
(4) W. Markownikoff, Ann. 327, 59, 1903.
(5) W. Markownikoff, J. Russ. Phys. Chem. Soc. 34, 908, 1902.
(6) W. Markownikoff and Jakub, J. Russ. Phys. Chem. Soc. 34, 914, 1902.
(7) N. A. Rosanow, J. Russ. Phys. Chem. Soc. 48, 309, 1916.
(8) N. A. Rosanow, J. Russ. Phys, Chem. Soc. 61, 2313, 1929.
(9) L. Ruzicka and C. F. Seidel, Helv. Chim. Acta, 19, 424, 1936.
(10) L. Ruzicka, M. Stoll, H. Huyser, and W. A. Boekenoogen, Helv. Chim. Acta, 13, 1152, 1930.
(11) A. I. Vogel, J. Chem. Soc. 1938, 1323.
(12) R. Willstatter and T. Kametaka, Ber. 41, 1480, 1908.
(13) N. D. Zelinsky, J. Russ. Phys. Chem. Soc. 37, 962, 1905.
(14) N. D. Zelinsky, J. Russ, Phys. Chem. Soc. 38, 473, 1906.
141
Name and Carbon Skeleton
M. P.C.
B. P., C.
760mm
iff
-B
Additional Data
Cyclooctane
0.8304 7
1.4563
dD_ Oooog69/ o c
O
14.2 to
14.4 19
14 20
145.3 to
146.3 "
146.5
0.7800 7
@ 78.3
0.7800 14
1.4558
1.45777 18
1.4586 19 - 22
rf/ (10 to 80)
13 to 14 22
@ 752mm
@78
1.4610 >
11.5 18
148.5 to
0.7947 8
@13.5
9.5 to
11.5 1
149.5 22
@ 749mm
@61.2
0.8296 7
1.4641 14
144 7
0.830 14
*c
@ 730mm
0.833 2 - 18
1.4573 u
ft 18
147 to 148 2
0.8349 22
@ 720mm
0.835 lfl
1.4662"
145.3 to 148 18
wl5
@ 720mm
149.6 to
0.839 19
0.841 20
1 .4545 I4
150.6 19
0.831 8 8
n " e r
@ 709mm
@17
39 to 42 "
0.8332 7
@ 15mm
@ 15.8
0.8396"
D 13 ' 8
0.850 18
0.855 20
@0
MethylcycloSctane
c
14 to 16 >
160 to 163
0.8349
1.4567 3
@ 750mm
0.8405 >
@ 13.5
148.5 22
^JJ.6
@ 749mm
C ft Hit
142
Name and Carbon Skeleton
\r r> (>/"
M. Jr., C-.
J5. P., C.
760mm
Iff
n-
Additional Data
Cyclononane
170 to 172 21
0.7733 2l
1.4328 21
16
16
0.785 21
CioMso
Cyclodecane
9.6 4tl6
201 4
0.8577 4
1. 46922 4
82 16mm 4
20.4
wS.
0.8584 4
19.6
1.47758 4
20
1.48242*
1.47181 4
Cycloundecane
183.5 to 184.5
0.81284 6
1. 44834 5
764.5mm 6
0.8002
1 79 to 181
14
0.81 19
Cyclododecane
dD
61"
118"
0.8223 "
dt (55 to 75)
18mm
75
0.8340"
58
143
Name and Carbon Skeleton
M. P.,C
B. P. t C.
@ 760mm
D?
B
Additional Data
Cyclotridecane
^=-0.0007/C
dt (15 to 35)
18"
112 to 113"
0.8513"
@9mm
33.5
'
0.8608 "
0.8636"
16
Cyclotetradecane
53"
143"
0.8259 "
1.4515"
16mm
79
80
0.8284 "
1.4533"
75
n H. t
1.4506"
1.4623 "
"16*130
Cyclopentadecane
=-0.0006,/C.
d * (75 to 110)
61"
0.8048 "
1.4522"
109
80
0.8240"
1.4448"
78
n n\
0.828 "
71
1.4554 "
1.4528 "
1.4644 "
C ii Has
144
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
B
Additional Data
Methylcyclopenta-
decane
0.8585,
^=-0.0006200
(1-0.0004990/C.
-19"
147 to 148
0.8051 "
1.4735"
(20 to 80)
@> 12mm
@109
@21
0.8227 8
1.4438"
@ 79.2
W 102
*'/
0.8337 8
1.4716"
@60.9 C
0.8475 8
He f
@ 34.5
1.4837"
0.8576
n n*.
21
0.8593 8
20.3
0.858 14
0.8594 "
19
Cyclohexadecane
57 14
170 to 171 "
0.819"
1.4529"
61
@ 20mm
79
@80
0.824 "
1.4557"
@72
145
Name and Carbon Skekton
M. P.,C
B. P., C.
(& 760mm
iff
5
Additional Data
Cycloheptadecane
65"
0.8021 "
1.4507"
-=~0.00058/C.
(75 to 110)
108
80
0.8062 "
1.4436"
101
w i?i
0.8200 "
1.4409"
^r
1.4524"
Cyclooctadecane
72 t,i4
0.7998 "
1.4506 "
dt (75 to 110)
111
80
0.8201 "
1.4427 "
76
n n\ f
1.4533 "
1.4399 "
r
1.4506"
r
1.4514"
1.4624 "
a *i
146
Name and Carbon Skeleton
M. P.C.
B. P., C.
@ 760mm
D?
nl
Additional Data
Cyclodocosane
46"
212"
0.8174"
1.4481 "
@ 16mm
@75
(480
1.4499"
1.4472 l4
1.4589"
/7 *
I/ g| XI 4B
Cyclotricosane
0.8280
^=-0.0002870
@60
d (l-f0.0128 3 0/C.
49 to
177 13
0.7973 "
1.4558"
(55 to 110)
50 u
@ 0.4mm
@111
@56
56"
0.8233 "
@69
0.8259
@64
0.8305 13
@55
Cyclotetracosane
47"
222 to 228 "
@ 0.6mm
147
CM lisa
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
D?
5
Additional Data
Cyclohexacosane
0.8238
dD
60
dt (60 to 115")
41 to
218 to 219"
0.7924 "
1.4484 "
42 10
@ 0.5mm
@ 112
@80
42"
0.8120"
1.4463 "
@78
H H*
0.8255 10
@58
1.4491 12
M 78
'/
1.4536 12
1.4558"
n \
1.4580"
Cyclooctacosane
47 to
213 to 214"
0.8103 "
1.4489"
48 10
@ 0.25mm
@80
@80
48"
0.813"
@76
0.8243 l
@58
148
Name and Carbon Skeleton
M. F.,C.
B. P., C.
(& 760mm
/*
R
Additional Data
Cyclononacosane
^=-0.0006 4 ,>C.
47 14
0.8232 "
dt (35 to 65)
0.8429 u
33
Cyclotriacontane
0.8294
60
dt (60 to 110)
53 to
230 10
0.7973 "
1.4401 lo
54
0.2mm
111
114
56"
0.8180"
1.4523"
57.8 10
77
80
0.8219 l
1.4555 10
73
71
0.8233 "
0.8308 "
58
C M H,<
1,16-Dimethylcyclo-
triacontane
52
0.808 *
1.4498'
89.3
80
0.813 7
80
149
C H
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
iff
5
Additional Data
Cyclodotriacontane
59 to
0.8261 10
1.4568 10
60"
70
70
1.4590"
63
Cyclotetratriacontane
~=-0.00033 7 /C.
(75 to 150)
66 to
230 to 240 M
0.8229 lo
1.4302"
67 10
0.3mm
76
151
1.4443 "
107
1.4568
72
(1) M. Godchot, Bull. soc. chim. [5] 1, 1153, 1934.
(2) M. Godchot, Compt. rend. 172, 686, 1921.
(3) M. Godchot and G. Cauquil, Compt. rend. 191, 1326, 1930.
(4) W. Huckel, A. Gerche, and A. Gross, Ber. 66, 563, 1933.
(5) G. Komppa, Ann. acad. sci. Fennicae, ser A. 30, No. 16; 15, 1930.
(6) W. Markownikow and Ogloblin, J. Russ. Phys. Chem. Soc. 15, 335, 1883.
(7) L. Ruzicka and H. A. Boekenoogen, Helv. Chim. Acta 14, 1319, 1931.
(8) L. Ruzicka, H. A. Boekenoogen, and H. Edelman, Helv. Chim. Acta 16, 487, 1933.
(9) L. Ruzicka, W. Brugger, C. F. Seidel, and H. Schinz, Helv. Chim. Acta 11, 496, 1928.
(10) L. Ruzicka, M. Hurbin, and M. Furter, Helv. Chim. Acta 17, 78, 1934. '
(11) L. Ruzicka, H. Schinz, and M. Pfeiffer, Helv. Chim. Acta 11, 700, 1928.
(12) L. Ruzicka and C. F. Seidel, Helv. Chim. Acta 19, 424, 1936.
(13) L. Ruzicka and M. Stoll, Helv. Chim. Acta 16, 493, 1933.
(14) L. Ruzicka, M. Stoll, H. Huyser, and H. A. Boekenoogen, Helv. Chim. Acta 13, 1152, 1930.
(15) R. Stratford, Ann. combustibles liquides 4, 83, 1929.
(16) R. Willstatter and J. Bruce, Ber. 40, 3979, 1907.
(17) R. Willstatter and M. Heidelberger, Ber. 46, 517, 1913.
(18) R. Willstatter and H. Veraguth, Ber. 40, 957, 1907.
(19) R. Willstatter and E. Waser, Ber. 43, 1176, 1910.
(20) R. Willstatter and E. Waser, Ber. 44, 3423, 1911.
(21) N. D. Zelinsky, Ber, 40, 3277, 1907.
(22) N, D. Zelinsky and M. G. Friemann, Ber. 63, 1485, 1930.
CsH, 150
2. CYCLANES WITH AN ALKENYL OR OLEFIN SUBSTITUTION
Name and Carbon Skeleton
M p r
Ml . JT f \*> .
B. P., C.
760mm
iff
^
Additional Data
Ethylidenecyclopropane
^=-0.001,/C.
rf * (0 to 20)
c-c
37.5
0.7052
1.40255 6
II
750mm
18
18
A
0.7235
Cyclopropylethylene
0.721
^
dt (0 to 20)
(Bthenylcyclopropane)
40 to 40.2
0.723
1.4172 ^
@ 755mm
18
15
OC
|
0.726
1.4205
A
15
0.7311
10
10
0.741 5 4
CeHio
2-Cy clopropylpropene- 1
(Isopropenylcyclopropane)
71.1 to 71.5 ">
0.74999 7
1.4252
@ 772mm
0.7510'
1.42524'
OC-C
69.5 to 70.0 7
1. 42064 7
@ 751mm
w ^
1. 43206 7
"B,
151
Name and Carbon Skeleton
Mp /~'
. f., C.
B. P., C.
@ 760mm
Iff
B
Additional Data
Isopropylidenecyclo-
propane
(2-Cyclopfopylidcne-
70.5 to 71 >
0.7531 '
1.424 >
propane)
@ 763mm
1.4264 12
71 to 71.5"
@17 C
r-c-c
@ 718mm
A
Cltr
7 Jd-12
2-Cyclopropylbutene- 1
c=c-c-c
103.5 to
0.7772'
1.43901 '
I
103.8 7
1.43569'
/\
a
1.44926'
1.45515'
T
2-Cyclopropylbutene-2
( 1 -Methylpropen- 1 -yl-
105.5 to 106'
0.7804 '
1.44253'
cyclopropane)
1.43861'
c-ooc
HH *
1
1.44926'
A
1.45515'
152
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
ng
Additional Data
3-Cyclopropylpentene-2
1.447
c-oooc
1
127.5 to 128 7
0.79150 *
1.44454 '
A
@ 762.5mm
129 to 130
0.7644 *
1.45841 *
1. 44159 7
1.45156 7
2,2-Dimethyl-
1- (2-methylpropen-
l-yl)-cyclopropane
c
1
ooc
1
132 8
@ 758mm
0.7677 8
0.7681 8
1.4420 8
A/
\
C
1,1-Dimethyl-
2-(2-methylprop-
ylidene)-cyclopropane
c c
-18
112"
A-J-c
CWMMM* = V/ V/ \S
153
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
iff
20
Additional Data
l-Methyl-l-(3-methyl-
penten-l~yl)-cyclb-
propane
c
162 to 162,7
1
c oc-c-c-c
160 to 160.5 9
@ 735mm
A
(1) D. Alexejewa, J. Russ, Phys. Chem. Soc. 37, 419, 1905.
(2) P. Bruylants, Rec. trav. chim. 28, 188, 1909.
(4) N. J. Demjanow and M. Dojarenko, Ber. 55, 2718, 1922.
(5) G. Gustavson, J. prakt. Chem. [2] 54, 99, 1896.
(6) Jelocnik, Monatsh, 24, 527, 1903.
(7) N. v. Keersbilck, Bull. soc. chim. Belg. 38, 205, 1929.
(8) N. Kishner, J. Russ. Phys. Chem. Soc. 45, 957, 1913.
(9) N. Kishner, J. Russ. Phys. Chem. Soc. 50, 8, 1921.
(10) N. Kishner and Klawikordow, J. Russ. Phys. Chem. Soc. 43, 597, 1911.
(11) V. Lowy and E. Winterstein, Monatsh, 22, 399, 1901.
(12) N. D. Zelinsky, Ber. 40, 4743, 1907.
C,H.
154
Name and Carbon Skeleton
M P C
ML . JT f \st
B. P. t C.
@ 760mm
D?
5
Additional Data
Methylenecyclobutane
0.738 6
^= -0.00099/C.
c
42 3
0.7360 8
1.42353 .*
dt (0to25)
II
42*
@23
@ 15
@ 749mm
0.7425 ^ 2
1.42626 1 - 2
40.6 to 41. 6 '*
@ 15
@ 10
@ 732mm
0.7487
@10
0.7583 2
0.7585
3-Cyclobutylidene-
pentane
c~c~oc-c
II
0.8091 *
1.4510
II
O
(1) N. J. Demjanow and M. Dojarenko, J. Russ. Phys. Chem. Soc. 49, 199, 1917.
(2) N. J. Demjanow and M. Dojarenko, Ber. 55, 2727, 1922.
(3) O. Philipow, J. Russ. Phys. Chem. Soc. 46, 1163, 1914.
(4),O. Philipow, J. prakt. Chem. 93, 162, 1916.
(5) N. Kishner and Amosow, J. Russ. Phys. Chem. Soc. 37, 518, 1905.
155
Name and Carbon Skeleton
Af. P.,C.
B. P., C.
@ 760mm
DT
ng
Additional Data
Methylenecyclo-
pentane
0.778 7
= 0.001 0/C.
J/ (20 to 45)
c
77 to 79
0.7518*
1.4350 8
II
o
@ 767mm
78 to 81
75 to 76 8 *
76 to 78 8
@ 44.8
0.7541 te
42.7
0.7778 ta
@ 20.8
1. 43078 ta
1.43208
1.4351*
1.4355'
0.7770
0.7787 *>**
1.42808*
0.778'
a
1.43743 to
H
H f>
1.44257*
y*
Ethylidenecyclo-
pentane
c-c
II
O
1 13 to 117 12
0.8020 12
1.4481 12
l-Methylene-3-methyl-
cyclopentane
c
96 to 97 .
0.7734 "
1.4296"
1!
93.5 "
@19
@ 19
x\
0.7750 7 -
1.4336"
W
@16
@16
\
C
156
Name and Carbon Skeleton
M. P.,C.
B. P.,
@ 760mm
iff
*;
Additional Data
Isopropylidenecyclo-
pentane
c-c-c
136 to 137
0.817 ll
1.4581 ll
II
o
l-Cyclopentylpropene-2
(Allylcyclopentane)
C-OC
124 to 126
0.793
1.440 8
6
@23
l-Methyi-2-ethylidene-
cyclopentane
c
123 to 124 *
0.7995 6
1.4442 1 6
6C-C
x
157
Name and Carbon Skeleton
A/. JVC
(fr 760mtn
/>r
S
Additional Data
l-Cyclopentylbutene-2
(Buten-2-ylcyclopentane)
156 to 158
0.806 *
1.4482
@ 24.5
@25
C-C=C-C
1
O
l-Methyl-2-isopropyli-
denecyclopentane
c
149 to 15 1 4
0.81 04 4
1.4518 *
1 c-c
@ 755mm
D?
l-Methyl-2-isopro-
penylcyclopentane
c
141 to 143
0.8005
1.4455 <
1 c=c
@ 757mm
158
Name and Carbon Skeleton
M. P.,C
B. P. t C.
@ 760mm
tif
n*
Additional Data
l-Methylene-2,3,3-
trimethylcyclopentane
c
138 to 140 1
II c
o:
N
C
l-EthyIidene-3-iso-
propylcyclopentane
c-c
172 to 174 10
0.809 10
1.4506 10
c-c
1
c
l,2,2-Trimethyl-3-
ethenylcyclopentane
c
155 to 156 2
0.8024 s
1.4439 2
A/ c
24
@25
OS
c=c
159
(a) K. v. Auwers and P. Ellinger, Ann. 387, 201 (1912).
(1) L. Beauveault and G. Blanc, Compt. rend. 136, 1461, 1903.
(2) J. v. Braun and A. Heymons, Ber. 61, 2276, 1928.
(3) B. Grdy, Bull. soc. chim. [5] 2, 1029, 1935.
(4) N. Kishner, J. Russ. Phys. Chem. Soc. 44, 857, 1912.
(5) C. D. Nenitzescu and G. G. Vantu, Bull. soc. chim. [5] 2, 2209, 1935.
(6) L. Piaux and M. Bourguel, Ann. chim. [11] 4, 147, 1935.
(7) N. Speransky, J. Russ. Phys. Chem. Soc. 34, 24, 1902.
(8) A. I. Vogel, J. Chem. Soc. 1933, 1028.
(8a) A. I. Vogel, J. Chem. Soc. 1938, 1323.
(9) O. Wallach, Ann. 347, 325, 1906.
(10) O. Wallach, Ann. 384, 193, 1911.
(11) O. Wallach and A. Fleischer, Ann. 353, 304, 1907.
(12) O. Wallach and v. Martius, Ann. 365, 272, 1909.
(13) O. Wallach and N. Speransky, Nachr. Ges. Wiss. Gattingen, 1902, 92.
(14) N. D. Zefinsky, Ber. 34, 3950, 1901.
160
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
Iff
*J
Additional Data
Methylenecyclohexane
103.5
0.803 3
1.450,
^ 0.0008/-C.
d ' (0 to 60)
c
105 to 106 "
0.7704
1.4528"
770mm
61.0
1.45227 "
102 to 103
0.7867 3 *
1.4502 *
@ 764mm
41.5
{ft 3U
105tol06J^ 6 '
0.7872
40.9
3T '
1.4490"
103 to 106 ll - 37
0.7992
1.4491 to
103 to 104
0.801
1.4516"
102 to 103 "
0.8018 "
1.4486"
101 to 102 *
0.802 to
1.45092
102.5
0.804 w
17.8
@ 756mm
0.8025 "
1.45182 B
100.5 to
0.8032
16.4
101.3
0.8034 *
1.45222
756mm
0.8074
15.5
101.2 to 102
0.8034
1.45341
@ 751mm
17.8
13.2
104 M
0.8036 fl
1.44916"
749mm
17.6
""*
0.8097 35
1.44803*
17.5
wJJ- 8
0.8021 8
16.4
1. 44863 s
0.8055
* 7
15.6
1.44934
0.8056
n< H'*
15.5
1. 45053
0.8040 6
W 13.2
14
a
0.8184 w
1.45973 M
D 9
1. 45820
wg- 8
1. 45879*
1.45958"
1.46086-
-
161
C,H,,
Name and Carbon Skeleton
B. P., C.
(ft) 760mm
*
5
Additional Data
Methylenecyclohexane
(Continued)
1.46567 86
7
1.46430
*,17.8
a .
1. 46488 B
7
1. 46568
^16.6
7
1. 46696
-,13.2
n lf
7
CsH.14
Cyclohexylethylene
(Vinylcyclohexane)
131 to 132 22
0.8134 22
1. 4546 22
@ 750mm
0.8166 24
1. 4550 2 *
c=c
130 to 131 2 <
@ 19
@ 19
@, 749mm
162
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
Iff
n D
Additional Data
Ethylidenecyclohexane
137
c~c
136 to 136.4
0.8220 5
1.46299 s
JL
@ 766mm
@20.3
1.4626 44
f]
137 to 138
0.8220 4
1.4591
k^
135 to 136 13
0.8225
@ 19
134 to 136"
0.8235
1.4577 14
@19
19
0.8286 l *
1.4631 44
0.8230
1.46389'
@18
@ 17.6
0.8237 6
1. 46094
f~} 1 7 ^
]7 Q
Vj*/ 1 / . O
n H
0.8239
1.4596*
(m 1 7.3
w}J- :<
1.471398
n}}-*
1.47010 6
wJJ- 3
1.47773
7
t. 4763.3 s
n n"
7
l-Methylene-2-methyl-
cyclohexane
c
122 to 125 41
0.808 41
1.4516 41
II c
22
@ 22
0'
163
Name and Carbon Skeleton
M. P.C.
B. P., C.
760mm
iff
*
Additional Data
l-Methylene-3-methyl-
cyclohexane
0.795 8
[]-- 30.22 M
c
II
123 to 124 3 *
762mm
0.7610 38
61.9
1. 44626 36
1.4461 36
rf/ (15 to 65)
s-
C
1 23 to 124 3
0.7614 *
61.5
0.7778
42.1
0.794
0.7970
1.4466 36
18
1.44337
".
1.45336 36
0.797 *
18
H &
1.45887 36
0.8003 36
n /J
16.3
l-Methylene-4-methyl-
cyclohexane
121
0.798 6
1.446,
^ (15 to 90)
c
63 to
124 to 125 35 - 36
0.7407 36
1.4446 38 - 43
^ w
II
(\
64-18
772mm
122 to 123
87.3
0.7412 35 - 36
22
1.4483 2
^ (15 to 25)
u
c
122 2 M8
120 to 121 2
86.7
0.7634 35 ' 3fl
60.9
f35,
1.44626J 36
1.4450"
0.7925 43
22
t.4465 29
18
0.7920 37
1. 44339 M
^20
g
0.7945 2
0.7996 35 - 39
1. 45338 s6
0.7923 2B
1. 45890 M
0.8033 3 *. 39
w /5 7
15.9
164
Name and Carbon Skeleton
/.P,-C.
B. P., C.
@ 760mm
7)5
M'
Additional Data
Isopropylidenecyclo-
hexane
(2- Cyclohexylidenepropane)
160 to 161 45
0.836 45
i.4723 46
52 to 153 '
C-C-C
||
@ 740mm
ii
O
Isopropenylcyclo-
hexane
(2-Cyclohexylpropene- 1 )
157 to J58 25
C=OC
6
l-Cyclohexylpropene-2
0.816 ?
1.450.
^p= -0.0007,/C.
dt (0 to 45)
(Allylcyclohexane)
154 to 154.4 2
0.8010"
1.4483"
152 8
41.5
25
n (\C\C\A. lc*
= ~~U.UUU^j/ v>
C-OC
1
149 to 151 23
0.8117"
1.449*
rf/ (10 to 25)
O
148 to 140 "
148 to 149 M
28.5
0.808 8
21
21
1.454 M
1.4528"
0.8160 1T
15
0.8156
1.45362*
0.8196
13
13
1.452*
0.813
13
0.83 12
165
Name and Carbon Skeleton
Af . P.,C.
B. P., C.
@ 760mm
or
s
Additional Data
l-Methyl-2-ethylidene-
cyclohexane
c
158 27
0.81 27
1.47"
1 c-c
//?V Q1
OS
(gj ol
0.823 27
l-Methyl-3-ethylidene-
cyclohexane
c
153 44
0.813
1.4584 44R
152
0.8135 18
1.4590 15
vll
@19
\
c-c
l-Methyl-4-ethylidene-
cyclohexane
c
152 to 153 4B
0.810 49
1.4571 49
@21
@ 21
0.812 4
1.4574 49
II
c-c
166
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
s
Additional Data
l-Methylene-3,3-di-
methylcyclohexane
c
138 to 141"
0.7970 12
1.44837 *
II
@ 739mm
@ 16.5
@ 10
0<
0.8013 12
c
2-Methylene-l,4-di-
methylcyclohexane
c
135 to 136 fl
0.7922 6
1.446*
1 c
@ 764mm
@ 14.1
@ 14.6
^/
\
c
l-MethyleAe-3,5-
dimethylcyclohexane
c
135 to 136 4 - 6
0.7918
1.44628*
II
@ 744mm
@ 14.6
@ 14.6
A
0.7922 4 -
1. 44334 6
n a
a
c c
1.45313
1.45917
-14.6
*,
167
Name and Carbon Skeleton
M. P.C.
B. P., C.
@ 760mm
D?
8
Additional Data
l-Cyclohexylbutene-2
(Buten-2-ylcyclohexane)
177 s
0.813 8
1.453 8
66 @ 14mm 7
21
@21
C-OC-C
0.818 8
1.457 8
13
l-Cyclohexylbutene-3
(Buten-3-ylcyclohexane)
174.5 to 175 22
0.810 8
1.450*
174 8
@ 21
21
c-c-c=c
!
62 @ 14mm 8
0.8131 22
1.453"
O
1 -Cyclohexylbutene-*
0.815 8
1.454 s
13
l-Methyl-2-isopropyli-
denecyclohexane
c
160 to 162 42
0.8345 42
1.4670 42
c 1
1 c-c
a
168
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Z>f
n*
Additional Data
l-Methyl-3-propyli-
denecyclohexane
[ a ]^-34 28'
c
170 to 173 4
0.814 48
1.4591
1
@ 19
@ 19
Ox
c-c-c
l-Mthyl-4-isopropyli-
denecyclohexane
c
172 to 174
0.831 38
1.4647 38
o
@21
21
V
c-c-c
M-Methyl-3-isopro-
[^--0.51^
pylidenecyclohexane
c
173 to 175 42
0.8250 * 2
1.4569 21
Ox
1 72.5 to
174.5"
@ 749mm
0.8214 21
1.4577 21
1.4582 21
1.4670 42
c-c
1
c
169
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
Iff
n-
Additional Data
d-l-Methyl-3-isp-
l Jx ,-+9.73 e .
propenylcyclohexane
c
170 to 1 70.5
0.81 78 8i
1.4546"
a
@ 751mm
D?
c=c
1
1
c
M~Methyl-3-iso-
lJ I ,--8.06 OM
propenylcyclohexane
170 to 171 20
0.81 85 20
1.4574 M
% 749mm
tif
l-Methylene-4-iso-
propylcyclohexane
c
11
r-~-i
0.8667 18
1.4840 18
V
c-c-c
C id AH
170
Name and Carbon Skeleton
Jf. P.,C.
B. P., C.
@ 760mm
elf
-8
Additional Data
l-Methyl-4-propyll-
denecyclohexane
c
175 to 177 48
0.8110"
1.4571 40
1
173 to 174 40
0.8135
1.4516
19
@ 19
T
c-c-c
l-Methyl-4-isopropyli-
denecyclohexane
(-Menthene-4)
1 72 to
0.8189 32
1.4647 M
174 fl,3e.40
D
1.4670 40
C
170 to 172 7
0.8345
1.45922 7
169 to 170 32
0.831 3
1. 45862 7
@ 748mm
@21
1.45823 32
II
0.819 7
II
C-C-C
@21
0.8175 7
@ 20.5
l-Methyl-4-isopro-
penylcyclohexane
(Dihydrolimonene)
170 19
0.821 7 32
1. 45673 M
@ 750mrn
@21
@ 21
C
168 to 169 32
0.8142 1S
1.45662"
6
@ 750mm
1 70 to 170.5 M
@ 746mm
r-^20
0.8104 33
0.810 23
1.4523 19
1
53 to 54
D 16
c-c=c
@ 14mm
171
Name and Carbon Skeleton
M. P.C
B. P., C.
@ 760mm
DT
"S
Additional Data
l-Methylene-2,3,3*tri-
methylcyclohexane
( Methyl- Y-geraniolene)
164
@ 738mm
0.8320
1. 46274 u
C
1! c
1.464 14 12
@n
c
Ctl J120
1-Cyclohexylpentene-x
c-c-c-c-c
1
196 8
0.816 8
1.454 s
O
83 @ 14mm 8
2-Cyclohexylpentene-l
oc-c-c-c
6
198 to 199 8
85 @ 16mm 8
0.822 8
1.458 s
4-Cyclohexylpentene-2
c-c=c-c~c
6
125.3 to 126.3
@ 95mm 2
0.8322 2
@25
1.4595 2fl
@25
172
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
n D
Additional Data
l-Methyl-3-(2-methyl-
propen-2-yl)-cyclo-
hexane
c
186.5 to
0.8120 47
1.4546 47
a
c-oc
1
c
187.5 47
2-Methylene-4-methyl-
1-isopropylcyclohexane
H.-^.
c-c-c
r^r^ c
181 to 182 '
0.8273
@16
i
c
l-Methylene-3,3-di-
methyl-2-ethylcyclo-
hexane
(Ethyl-7-geraniolene)
182 to 184 12
@ 745mm
0.8160 12
1.46235 12
@ 10
c
II c-c
c
173
Name and Carbon Skeleton
/. /vc.
B. P., C.
(fr 760mm
D?
s
Additional Data
l-Methylene-2,2,3,3-
tetramethylcyclohetane
(Dimethyl-'y-
81 to 183 12
0.8246 12
1.46275 12
cyclogeraniolene)
@ 756mm
11
@12
C
||
O1
1-Cyclohexylhexene-x
c-oc-c-c~c
219 8
0.820 8
1.4S7 1
6
99 @ 16mm 8
2-Cyclohexylhexene-x
c-c-c-c-c-c
221 8
0.823 8
1.459 8
1
102 8
@ 21
@21
O
@ 17mm
174
Name and Carbon Skeleton
Of P C
JXt, JTtf L/.
B. P., C.
@ 760mm
Iff
-B
Additional Data
5-Methyl-l-ethylidene-
Wg +34.79
2-isopropylcyclo-
hexane
c-c
58 to 59 J
0,8304 '
@ 4mm
@ 16
-c-c
1
c
c
l-Methylene-3,3-di-
methyl-2-propylcyclo-
hexane
(Propyl-7-cyclogeraniolene)
200 to 202 12
0.8126 12
1.46176"
@ 741mm
@ 10
@ 10.5
C
83 to 85 12
II c-c-c
@ 12mm
4-Cyclohexylheptene-2
c-o=c-c-c-c-c
135.6 to
0.8355 2 <
1.4630 24
1
136.6 24
@25
25
0'
@45mm
175
C it
Name and Carbon Skeleton
l.f n 0/"
M. r , t C.
B. P., C.
@ 760mm
D?
Additional Data
4-Cyclohexylheptene-x
c-c-c-c-c-c-c
226 to 228 *
0.8441 3
1.467 3
6
@ 755mm
@21
1-MethyW-propyU-
dene-4-isopropylcyclo-
hexane
c
0.8129 l
A
@ 16.5
I c-c-c
c-c-c
l-Methylene-3,3-di-
methyl-2- (2-methyl-
propyl)-cyclohexane
(Isobutyl-7-cyclo-
212 to 213
0.8112
1. 46086 12
geraniolene)
@ 742mm
@ll
11
C
c I
|| c-c-c
_
176
Name and Carbon Skeleton
(ft) 760mm
iff
*
Additional Data
l-Methyl-4-isopropyl-
2-(3-methylbuten-2-
yl)-cyclohexane
c
127 to 128
0.8418
1.4702'
| c-o=c-c
@ 19mm
pS5
@ 25
O/ 1
c-c-c
C 19 Has
2-Methylene-l,l,3,3-
tetrapropylcyclohexane
c-c-c c-c-c
165 10
0.861 8 10
1.4800 10
c
@ 15mm
@ 16 P
@ 16
c-c-c
177
(1) Akira Ogata and Chuji Mizashita, J. Pharra. Soc. Japan, 1922, No. 484, 4.
(2) N. Alexandrovitch, J. Gen. Chem. (U.S.S.R.) 3, (65) 48, 1933.
(3) G. Amouroux and M. Murat, Compt. rend. 154, 994, 1912.
(4) K. v. Auwers and 'P. Eliinger/ Ann. 387, 200, 1912.
(5) K. v. Auwers and P. Ellinger, Ann. 387, 219, 1912.
(6) K. v. Auwers, R. Hinterseber, and W. Treppmann, Ann. 410, 257, 1915.
(7) A. Belial, Compt. rend. 150, 1764, 1910.
(8) M. Bourguel, Bull soc. chim. [4] 41, 1475, 1927.
(9) A. E. Bradfield, E. R. Jones, and J. L. Simonsen, J. Chem. Soc. 1934, 1810.
(10) R. Cornubert, C. Borrel, M. De Demo, J. Gamier, R. Humeau, H. Le Bihan, and G. Sarkis, Bui!
soc. chim. [5] 2, 195, 1935.
(11) P. Ebel, R. Brunner, and P. Mangelli, Helv. Chim. Acta 12, 19, 1929.
(12) R. Escourrou, Bull. soc. chim. [4] 39, 1460, 1926.
(13) A. Favorsky and I. Borgmann, Ber. 40, 4863, 1907.
(14) M. M. Godchot and G. Cauquil, Compt. rend. 186, 375, 1928.
(15) W. N. Haworth, W. H. Perkin, and 0. Wallach, Ann. 379, 144, 1911.
(16) C. Hell and O. Schaal, Ber. 40, 4162, 1907.
(17) C. D. Kurd and H. T. Bollman, J. Am. Chem. Soc. 55, 699, 1933.
(18) M. A. Iskenderov, J. Gen. Chem. (U.S.S.R.) 7, 1435, 1937.
(19) N. Kishner, J. Russ. Phys. Chem. Soc. 43, 951, 1911.
(20) N. Kishner, J. Russ. Phys, Chem. Soc. 43, 1560, 1911.
(21) N. Kishner and Sawadowski, J. Russ. Phys. Chem. Soc. 43, 1139, 1911.
(22) R. Y. Levina and A. A. Potopova, J. Gen. Chem. (U.S.S.R.) 7, 353, 1937.
(23) R. Y. Levina and D. M. Trakhtenberg, J. Gen. Chem. (U.S.S.R.) 6, 764, 1936.
(24) R. Y. Levina and F. F. Zurikow, J. Gen. Chem. (U.S.S.R.) 6, 1250, 1936.
(25) K. Matsubara and W. H. Perkin, J. Chem. Soc. 87, 661, 1905.
(26) S. P. Mulliken, R. L. Wakeman, and H. T. Gerry, J. Am. Chem. Soc. 57, 1605, 1935.
(27) M. Murat and G. Amouroux, Bull. soc. chim. [4] 15, 159, 1914.
(28) W. H. Perkin and S. S. Pickles, J. Chem. Soc. 87, 639, 1905.
(29) W. H. Perkin and W. J. Pope, J. Chem. Soc. 99, 1514, 1911.
(30) B. de Resseguier, Bull. soc. chim. [4] 7, 432, 1910.
(31) N. A. Rosanow, J. Russ. Phys. Chem. Soc. 48, 316, 1916.
(32) F. W. Semmler and J. Feldstein, Ber. 47, 384, 1914.
(33) F. W. Semmler and C. Rimpel, Ber. 39, 2582 r 1906.
(34) A. I. Vogel, J. Chem. Soc. 1933, 1028.
(35) A. I. Vogel, J. Chem. Soc. 1938, 1323.
(36) 0. Wallach, Ann. 347, 342, 1906.
(37) O. Wallach, Ann. 359, 291, 1908.
(38) 0. Wallach, Ann. 365, 255, 1909.
(39) O. Wallach, Ber. 39, 2504, 1906.
(40) O. Wallach and L, Augsperger, Ann. 414, 212, 1918.
(41) 0. Wallach and E. Beschke, Ann. 347, 338, 1906.
(42) 0. Wallach and J. B. Churchill, Ann. 360, 80, 1908.
(43) 0. Wallach and E. Evans, Ann. 347, 345, 1906.
(44) 0. Wallach and E. Evans, Ann. 360, 45, 1908.
(44a) O. Wallach and E. Evans, Ann. 360, 51, 1908.
(45) 0. Wallach and H. Mallison, Ann. 360, 68, 1908.
(46) 0. Wallach and P. Mendelsohn-Bartholdy, Ann. 360, 48, 1908.
(47) O. Wallach and W. v. Rechenberg, Ann. 394, 362, 1912.
(48) O. Wallach and M. Rentschler, Ann. 360, 60, 1908.
(49) O. Wallach and M. Rentschler, Ann. 365, 269, 1909.
178
Name and Carbon Skeleton
M. P.,C.
B. P., C.
% 760mm
Iff
*S
Additional Data
Methylenecyclo-
heptane
c
6
138 to 140'
0.824 l -
1.461 1 1
(1) 0. Wallach, Ann. 345, 139, 1906.
(2) O. Wallach and van Beeck-Vollenhoven, Ann. 314, 156, 1900.
179
3. CYCLANES WITH TWO ALKENYL OR TWO OLEFIN
SUBSTITUTIONS, C.H,._,
C.H,
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D?
w"
Additional Data
1 ,2-Dimethylenecyclo-
butane
c
<>
63 to 65 4
0.7698
1.42317 <
1 ,2-Diisopropylidene-
cyclobutane
dt (0 to 20)
c-c-c
II
179 to 181 2
61 to 62 2
0.8422 2
0.8571 2
1. 50086 2
@ 19.7
r
@ 9mm
@0
1. 50622 2
a
1.51251 s
1. 52345 s
**19 7
2-Methylene-l,l-di-
methyl-3-isopropyli-
denecyclobutane
dt (0 to 20)
c c
V
149 to 150
@ 752mm
0.7982 2
0.8143 *
1.46769 2
@ 19.7
.
37 to 39 '
@0
1.46319*
-c
@9mm
W U' 7
c-c-c
1.47729*
ngjj
180
Name and Carbon Skeleton
2lf, P,,C.
J5. ?., C.
@ 760mm
iff
-!
Additional Data
l,2-Dimethyi-3,4-di-
ethylideaecyclobutane
c
163 7
0.8113 7
.47850 7
i
@ 762mm
1. 47423 T
c-c-A-c
65 @ 22mm 7
nj^
v
1.4891 3 7
II
n-
c-c
H ft
1.49838 7
7
l,2-Dimethylene-3,3,4,
4-tetramethyl-
cyclobutane
c
140 to 141 *
0.7927 6
1.4606 6
II
66 to 67 5
1.4570 5
C \/\ n
@ 55rnrn
w 20
y\ y^
a
c^XX
1.4699 5
/\
20
c c
"ft
1.4781 '
1 ,2-Dimethyl-3 ,4-di-
isopropylidenecyclo-
butane
c
190 to 191
0.8247
1.48337*
c 1
@ 754mm
1.47946*
'/ /s \
69 to 70
g
c-o^ y c
@ llmm
\/
1.49282*
II
n%
c-c-c
ft
1.50297
181
Name and Carbon Skeleton
B. P., C.
760mm
Iff
n*
Additional Data
1 ,2-Di-(l-ethylpropyli-
dene)-cyclobutane
c-c
1
c-c-c
II
102 to 104 8
@ 10mm
0.8569 8
16.5
1.48643
16.5
Or
c-c
1 , 1 ,2 ,2-Tetramethyl-3 ,
4-diisopropylidene-
cyclobutane
dt (0to20)
c c
86 to 88
0.8457 '
1. 49535 8
c ^^^
9mm
15.6
@ 15.6
' ' >^ /c
0.8563 8
C ~ C ~\/ ^c
II
c-c-c
c?- l-Methylene-4-iso-
propylidenecyclohexane
W.-r.
c
69 to 73
0.8515
1.4785
II
20mm
DZ
18
c-c-c
182
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
D ?
-s
Additional Data
l-Methylene-4-iso-
propenylcyclohexane
c
65 to 66
0.8735
1.4870 >
A
@ llmm
K
ooc
(1) M. A. Iskenderov, J. Gen. Chem. (U.S.S.R.) 7, 1435, 1937.
(2) S. Lebedev, J. Russ. Phys. Chem. Soc. 43, 820, 1911.
(4) S. Lebedev, J. Russ. Phys. Chem. Soc. 45, 1357, 1913.
(5) S. Lebedev, J. Russ. Phys. Chem. Soc. 45, 1373, 1913.
(6) S. Lebedev and B. Mereshkowsky, J. Russ. Phys. Chem. Soc. 45, 1348, 1913.
(7) S. Lebedev and B. Mereshkowsky, J. Russ. Phys. Chem. Soc. 45, 1354, 1913.
(8) B. Mereshkowsky, J. Russ. Phys. Chem. Soc. 45, 1940, 1913.
(9) P. Richter and W. Wolff, Ber. 60, 477, 1927; 63, 1714, 1930.
(10) O. Wallach, Ann. 359, 283, 1908.
183
4. CYCLANES WITH AN ALKADIENYL OR DIOLEFIN
SUBSTITUTION C.H,^
C.H,,
Name and Carbon Skeleton
TUT p r
JYL . JT . } {s
B. P., C.
@ 760mm
Iff
*8
Additional Data
Ethenylidenecyclo-
~-~ -0.0008 7 /C.
hexane
d ' (0 to 20)
c=c
138 to 141 l
0.8508
1.4826 1
O
0.8682 1
Dl
Propadienylcyclo-
hexane
c=c=c
155 to 156 '
0.8239 8
1.4658 8
1
@ 755mm
O
l-Methyl-4-isopropyl-
2-buten-2-ylidene-
cyclohexane
c
108 to 109 *
| c-c=c-c
@ 12mm
a
\
c c~c
184
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
^
n D
Additional Data
l-Methyl-4-isopropyl-
3-buten-2-ylidene-
cyclohexane
c
1
99(&12mm 4
Ox
| c-c=c c
c-c-c
M,7-Dimethyl-l-cyclo-
hexyloctadiene-1 ,6
c c
142 to 143 3
0.8468 3
1 1
@ 9mm
c=c-c-c-c-c=c-c
1
o
(1) W. Jegorowa, J. Russ. Phys. Chem. Soc. 43, 1119, 1911.
(2) R. Y. Levba and D. M. Trakhtenberg, J. Gen. Chem. (U.S.S.R.) 6, 764, 1936.
(3) H. Rupe, Ann. 402, 176, 1913.
(4) H. Rupe and A. Gassmann, Helv. Chini. Acta 12, 193, 1929.
(5) H. Rupe and Fr. Kuenzy, Helv. Chim. Acta 14, 708, 1931.
185
5. CYCLANES WITH AN ALKYNYL OR ACETYLENE
SUBSTITUTION, C.H,_,
Name and Carbon Skeleton
Tif p r
JXL (
B. P., C.
@ 760mm
D?
"S
Additional Data
Ethynylcyclopentane
c=c
107 to 109
0.825
1.4505 4
6
@22
@18
CTT
8 "42
1-Cyclopentylpropyne-l
(Propyn- 1 -ylcyclopentane)
142 to 143 4
0.843 4
1.4636 4
c=c-c
@22
22
6
3-Cyclopentylpropyne-l
(Propyn-2-ylcyclopentane)
132.5 to
0.828 5
1.4494 6
133.5 *
@24
@24
c-c=c
O
C,H,
186
Name and Carbon Skeleton
M. P.,C
B. P., *C.
760mm
Iff
g
Additional Data
l-Cyclopentylbutyne-2
(Butyn-2-ylcyclopentane)
164 to 165 6
0.842 *
1.462 1 6
@26
@ 26
C-C^C-C
6
C,H ia
Ethynylcyclohexane
=-0.00089/C.
c^c
130 to
0.832 *
1.4558 4
^ (0 to 20)
132
@23
23
0.8424
1.4597
0.8602
1-Cyclohexylpropyne-l
(Propyn- 1 -ylcyclohexane)
162 to 164*
0.85 1 4
1.4682
@ 22
22
C=C-C
1
O
187
Name and Carbon Skeleton
AT. P.,C.
B. P., C.
@ 760mm
iff
ng
Additional Data
3-Cyclohexylpropyne-l
C5C-C
157.5 to
0.836 '
1.459 1
1
160
0.8449
1.4605
@ 762mm
0.844
1.4603*
157 to 160 7
@18
@ 18
157 to 158
157 l
55 @ 17mm s
48 @ 12mm l
48 llmm 8
C 10 His
4-Cyclohexylbutyne-l
c=(>c _ c
70 @ 17mm*
0.8462 8
1.4614"
"6
61 to 62
@ 7mm
l-Cyclohexylbutyne-2
c-c=c-c
79 @ 17mm 3
1
O
188
Name and Cafbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D;
8
Additional Data
4-Cyclohexylpentyne-2
C-CSC-G-C
6
93 @ 17mm*
5-Cyclohexyl-
pentyne-1
C3C-C-C-C
84 @ 16mm 2
1
o
(5-Cyclohexyl-
hexyne-1
I
101 @ 16mm 2
O
189
Name and Carbon Skeleton
Af. P.,C.
fi. P., C.
($ 760mm
D?
n 20
Additional Data
6-Cyclohexyl-
hexyne-2
c-c=c-c-c-c
109 to HO 2
1
@ 17mm
O
(1) M. Bourguel, Compt. rend. 177, 688, 1923.
(2) M. Bourguel, Compt. rend. 179, 686, 1925.
(3) M. Bourguel, Ann. chim. [10] 3, 191, 1925.
(4) B. Gr&iy, Compt. rend. 199, 153, 1934.
(5) B. Gr&iy, Compt. rend. 199, 1129, 1934.
(6) W. Jegorowa, J. Russ. Phys. Chem. Soc. 43, 1119, 1911.
(7) R. Lespieau, Bull. soc. chim. [4] 29, 528, 1921.
(8) R. Levina and A. Ivanov, J. Gen. Chem. (U.S.S.R.) 7 (69), 1866, 1937.
(9) R. Levina and D. M. Trakhtenberg, J. Gen. Chem. (U.S.S.R.) 6, 764, 1936.
190
6. CYCLANES WITH A CYCLOALKENYL OR CYCLOOLEFIN
C, H,, SUBSTITUTION, CJ-U-i
Name and Carbon Skeleton
it/f n or*
JNL, M t L>
B. P., (> C.
@ 760mm
Iff
5
Additional Data
1-Cyclopentylcyclo-
pentene-1
o-o
189 to 191 "
@ 744mm
190
0.8898 18
1.499
1.50047
@ 730mm
n
l-Cyclopentylcyclo-
pentene-1 or -2
o-o
196.5 to 198
190*
83 to 85 3
0.8593 4
@ 22.5
0.9080 l7
1.4863
@22.5
1.4938 "
or
@ 20mm
@ 19.5
@ 19.5
o-o
82 to 83 <
@ 17mm
0.9183 *
18
1.4953 3
79 13mm*
1. 48284*
1. 49979 4
7
1-Cyclopentylcyclo-
pentene-2
o-o
63 @ 9mm l
0.8838 >
191
C ii
Name and Carbon Skeleton
M. /vr
B. P., C.
< 760mm
/>r
%
Additional Data
1-Cyclohexylcyclo
pentene-2
(Cyclopenten-2-ylcyclo-
80 to 85
0.8995 >
1. 48698
hexane)
@ 12mm
@18
o-o
C, 2 H 20
1-Cyclohexylcyclo-
hexene-1
(Cyclohexen- 1 -ylcyclo-
-41 8
238.5 18
0.9010 M
1.4910 1B
hexane)
237"
0.9086
1.4916 18
110 B
0.906 1S
1.4969 13
o-o
@13mm
100"
D 20
^20
0.9071
1. 49556 6
*!;:
@ 8.5mm
19.4
85 to 88 "
@4mm
Cyclohexylidenecyclo-
hexane
or
1-Cyclohexylcyclo-
hexene-1
oo
or
241"
124
@20mm
0.923
OO
C n HJO
192
Name and Carbon Skeleton
M. P.C.
B. P., C
760mm
DT
8
Additional Data
Cyclohexylidene-
cyclohexane
0=0
240 12
236 to 237
@ 742mm
1.0109 18
@15
1.4955 18
Cyclohexylcyclo-
hexene-x
o-o
-45 H
238 to 239 l4
103 to 105 14
@ 12mm
0.904 14
1.493 14
4-Methyl-l-cyclo-
hexylcyclohexene-1
or
4-MethyH-cyclo-
hexylidenecyclohexane
-o-o
158 8
@ 35mm
0.901 8
@10
1.489 8
@10
or
193
U [34
Name and Carbon Skeleton
M p r
Ml * j w<
B. P., C.
@ 760mm
D?
Additional Data
6-Ethyl- 1-cyclohexyl-
cyclohexene-1
dt (0 to 20)
Or~\
141 to 143 2
0.9274 2
1.5108*
~\-)
@ 20mm
0.9406 2
\
@o
c-c
d -3-Me thy 1- 1 - (5-meth-
ylcy clohexy 1) -cy clo-
[ a j, D = 4-0.28 8
hexene-1
c
257 to 259
0.9119 6
\
D 20
oo
0.9128 fl
Dl
\
c
Ci MSI
194
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
5
Additional Data
3-Methyl-6-isopropyl-
1-cyclohexylcyclo-
hexene-1
[a] D = -+-6.2 '
or
5-Methyl-2-isopropyl-
1-cyclohexylcyclo-
hexene-1
c
q-o
oc
1
c
265 7
260 7
@ 756mm
0.9198 '
14
0.9897 7
1.498 7
or
C
1
c-c
OO
C
(1) J. v. Braun, E. Kamp, and J. Kopp, Ber. 70B, 1750, 1937.
(2) C. E. Garland and E. E. Reid, J. Am. Chem. Soc. 47, 2333, 1925.
(3) M. Godchot and F. Taboury, Compt. rend. 154, 1626, 1912.
(4) C. Harries and H. Wagner, Ann. 410, 29, 1915.
(5) W. Huckel, O. Neunhoeffer, A. Gercke, and E. Frank, Ann. 477, 99, 1929.
(6) W. Markownikow, J. Russ. Phys. Chem. Soc. 35, 1069, 1903.
(7) M. Murat, J. pharm. chim. [7] 4, 297, 299, 1911.
(8) P. Sabatier and A. Mailhe, Ann. chim. [8] 10, 563, 1907.
(9) P. Sabatier and A. Mailh<, Compt. rend. 138, 1323, 1904.
(10) P. Sabatier and A. Mailhe*, Compt. rend. 139, 343, 1904.
(11) P. Sabatier and M. Murat, Compt. rend. 154, 1390, 1912.
(12) J. B. Senderens and J. Aboulenc, Compt. rend. 183, 830, 1926.
(13) F. K. Signaigo and P. L. Cramer, J. Am. Chem. Soc. 55, 3326, 1933.
(14) R. Truffault, Compt. rend. 200, 406, 1935.
(15) E. D. Venus-Danilova, J. Russ. Phys, Chem. Soc. 61, 1479, 1929.
(16) 0. Wallach, Ann. 381, 95, 1911.
(17) O. Wallach, Ann. 389, 181, 1912.
(18) N. D. Zelinsky, N. Shuikin, and L. Fatejev, J. Gen. Chem. (U.S.S.R.) 2, 671, 1932.
195
7. CYCLANES WITH A BICYCLENYL OR BICYCLOOLEFIN
SUBSTITUTION, C,,H 2 ,,,
Name and Carbon Skeleton
M, P.,C.
B. P., *C.
@ 760mm
D?
n i>
Additional Data
3-CyclohexyHO,4,4]-
bicyclodecene-3
(2-Cyclohexyl-A 2 -octahydro-
163 to 164 '
0.9422 *
1.51029 '
naphthalene)
^XX^X\/
^Sk. ^^*^- ^T
@ 13mm
2-Cyclohexyl-[0,4,4]-
bicyclodecene-(5-6)
162 to 163 >
0.9546
1.51754
@ 12mm
CO
(1) B. Albert!, Ann. 450, 304, 1926.
III. DICYCLANES OR DICYCLOPARAFFINS
1. Dicyclanes With Alkyl Substitutions, C n H 2 _j
199
1. DICYCLANES OR DICYCLOPARAFFINS, C.H,._,
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
tif
*8
Additional Data
Cyclopentylcyclo-
0.8616
1.4640
dv _ oooo756 OG
pentane
rf< (20 to 50)
(Dicyclopentyl)
189 to 191 l2 - 37
0,8389
1.4652
188 to 189 67
@50
1.4640
o-o
@ 753mm
189 to 190 M
0.8648 w
0.8612 12
1.4638"
1.4660 12
@ 750mm
0.8604 M
@15
CuH.20
Dicyclopentylmethane
o-o
208 to 2 10 42
0.8710 42
1. 46974
1 ,2-Dicyclopentylethane
OX\
206 to 207
0.8583
1.465 1 62
c c r j
@ 748mm
@22
@22
\ 1
109 to HO 44
0.8633 "
1.4657 44
@ 17mm
3-Methyl-l-(3-methyl-
cyclopentyl)-cyclo-
pentane
(3,3' Dimethyldicyclo-
46 to
218 to 219 M
0.8784 66
1.4755 66
pentyl)
47
213 to 215 M
0.8751 M
1.4755 66
213 to 214 M
@ 18.5
@18.5
YXT
@ 738mm
200
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
iff
-B
Additional Data
3-Ethyl-l-(3-ethylcyclo-
pentyl)-cyclopentane
(3,3' Diethyldicyclopentyl)
125 6
0.8757 6
1.47097 6
@ 15rnm
@ 15
c-c c-c
4,9-Dimethyl-5,8-di-
cyclopentyldodecane
(C) 8 -C-O-C-C-C-C-(C) 3
172 7
0.8690 7
1 1 1
@ 0.2mm
c 1 c
oo
201
w d
O\ oo O\ "^
rji CN rji -H
00
o
Ss3> < .CAS **
(2) oo (2) oq
odd
8 a Si
3 o 3 o *^
10 ^J ^ @
CM CS <N 00
Skel
and Ca
Na
s
B
o
202
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
t
Additional Data
Cyclopentylcyclo-
hexylmethane
oo
225 to 227 w
223 to 225 42
224to226 9 -
@ 750mm
0.872 !",
23
0.8681 42
0.8789 6
1.4671 "
@23
1.47131
1.4775
19
(2-Methylcyclopentyl)-
cyclohexane
( 1 -Methyl-2-cyclohexyl-
cyclopentane)
225.5 to 227 64
@ 744mm
0.8680 64
1.4701 64
C
/
0-0
(3-Methylcyclopentyl)-
cyclohexane
( 1 - Methyl -3 -cy clohexyl-
cyclopentane)
231 to233 61
0.8902 81
1.4787 61
\>o
203
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
Df
ft 20
Additional Data
(2-Methylcyclopentyl)-
cyclohexylmethane
c
1
239 to 241 *
0.8712 42
1.47369 42
oo
l-Cyclopentyl-2-cyclo-
hexylethane
o~o
251 to 252 10
@ 752.5mm
74 to 76
0.8780 10
0.8746
1.4775 10
@21
1.4723 45
@ 2mm
26
l-Cyclopentyl-3-cyclo-
hexylpropane
r"\ j^\
268 to 270 l
0.8751 10
1.4765 10
@ 748.2mm
204
Name and Carbon Skeleton
TUT P Q/~*
M. Jr., C.
B. P., C.
@ 760mm
D?
<
Additional Data
Cyclohexylcyclohexane
235
0.8846
1.4796
^=-0.000485/C.
(Dicyclohexyl)
_ 1 &7
233.5 to 235 41
0.8833 27
1.4772 27
(15 to 25)
]9
@ 762mm
@25
@25
o-o
2"
2.25 19
240 to 241 20
239.5 to 240 M
0.8947 "
@21.8
1.4740 39
1.4766 69
2.75 35
238 to 239 12
0.8862 "
1.4785 67
4 18,60
236.5 to
@ 20.6
1.4792 8 . 41
237.5 "
0.8790 39
1.4795 12
236 to 237.5 23
0.8804 6
1.4798"
235 29
0.8835 23
1.4800 14 - 66
234 to 236 4fl
0.8845 41
1.4842**
234 to 235 4
0.8847 M
1.47749.50
234 3 - 18
0.8848 12
@19
233 to 234 B0
0.8912 4
1.4815 22
233 49
0.8919 23
@18
231 to 233 27
0.877 M
1.4817 12
227 69
n 20
^20
@15
220 to 228 6
0.880 14
1. 47967 19
236 to 238 35
Dll
H H
@ 757. 5mm
0.8644 30
1.47977 l9
237 to 238.5 23
Dl Q
9)21.1
@ 757mm
0.8876
1.4795 19
236 to 238 64
@ 19.6
@ 754mm
0.873 49 - 50
H
234 to 236 80
Dl 9
1.4802"
@ 752mm
0.8777 30
U H
216 to 219 40
@0
1.4803"
@ 739mm
0.923 48
M 20
234"
D
@ 736mm
233"
@ 736mm
232.5 "
@ 736mm
124
@ 20mm
105"
@ 15mm
205
C 18 H 24
Name and Carbon Skeleton
M p r
JLKl * *) V"
B. P., C.
760mm
D?
<
Additional Data
Dicyclohexylmethane
251
0.8808
^= S ~0.000783/C.
oo
250 to 252 24
@ 763mm
251.5 13
0.8342 1S
@ 79.5
0.8884 J
1.4755 21
1.4752 7
(20 to 80)
250 to 252 7
0.8750 7
1.4875 J
250 to 25 1 49
0.8851 21
1.4786 2l
150 13
D 80
1.45053"
@45mm
0.8829 "
w 7 ^- 5
110 to 110.5 i
D 20
1.47475 13
@ 18mm
0.8743 21
n J
a
Dj
1.45862 l3
0.8765 13
n 70 - 5
H
@ 19.7
8
1.48328 13
1. 46336 13
7
1. 48828 13
7
2-Methyl-l-cyclohexyl-
cyclohexane
(2-Methyldicyclohexyl)
131 to 133.5 17
0.9058 17
1.4968 17
@ 20mm
0.9203 17
C
o-b
@0
3-Methyl-l-cyclohexyl-
cyclohexane
(3-Methyldicyclohexyl)
243 to 243.5 43
0.88668 43
1.4840
240 34
0.9138
1.492 34
C
@ 18
o-o
0.9634 34
@0
206
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
-s
Additional Data
1 ,1-Dicyclohexylethane
O
h
256 to 257] 60 -
I"
0.9070 l
0.9271 "
1.4887 >
@25
1.500 49
1
264 to 265 *
0.9130 49
1.511"
oc
@ 740mm
tif
112 7mm 1
1 ,2-Dicyclohexylethane
0.877
1.4768
dn
dt (15 to 25)
o-o
263 to 264 16
274 to 275.5 20
273 12
0.8758 8
0.8795 45
1.4749 8
1.4765
270 to 271 49 60
0.8760 12
1.480 49 - 60
266 to 268 M
0.8772 M
@ 18
@ 748mm
n 20
1^20
1.4760
@ 18
145 to 150
@ 20mm
0.8838 49 - BO
1.4790"
133 to 134"
0.8774
@15
@ 13.5mm
147 to 148.5 l
@ 12mm
132
93 to 94
(^ 2mm
207
Name and Carbon Skeleton
B. P., C.
(']) 760mm
iff
"7.
Additional Pata
2-Ethyl-l-cyclohexyl-
cyclohexane
(2-Ethyldicyclohexyl)
141 to 142.5
0.9126
1.4964
@ 20mm
0.9240
C-C
\
@0
o-o
J-3-Methyl-l-(3-
methyl-cyclohexyl)-
cyclohexane
(3,3' Dimethyldicyclo-
264 3l
0.8803 3l
hcxyl)
@ 761mm
Dll
148 to 149 31
0.8789 31
C C
@30mm
D?
o-o
0.8924 3l
4-Methyl-l-(4-methyl-
cyclohexyl)-cyclohexane
(4,4' Dimethyjdicyclohexyl)
C \ / \ /~ C
240 to 242 6
C 16 XI 2 1
208
Name and Carbon Skeleton
Tuf p r
JVJL. Jr., C'.
B. P., C.
@ 760mm
Iff
-8
Additional Data
1 ,1-Dicyclohexyl-
propane
dt (0 to 20)
270 to 271 - 62
0.8887 49 - M
1.485 41 - 12
Dl*
@23
0.9038 49 - 62
c-c-c
6
Do
1,2-Dicyclohexyl-
propane
^ (0 to 20)
Q-c-c-c
272 to 273 49 - 62
0.8725 49 - 62
0.8891 49 - 62
21
til
1,3-Dicyclohexyl-
propane
dt (0 to 20)
o~o
~30 lfl
291 to 292
289 to 290 49 - 62
0.8752
n 24
^24
0.8701 49 - 62
1.4736"
l.47S- w
0.8874 49 - 52
Dl
209
Name and Carbpn Skeleton
AJT. P.,C
B. P., C.
760mm
D?
"S
/I dditional Data
2,2-Dicyclohexyl-
dD__ om6 OG
propane
*" (0 to 20)
O
273 to 274 49 - 62
0.9002 49 - 62
D n
0.9158 49 - 62
1.490 "
c-c-c
Dl
1
O
1,1-Dicyclohexyl-
butane
280 to 282 ' 6
0.8842 - 53
1.485 49 - 63
r> 16
//o
@16
|
0.8922
oc-c-c
Dl
1
1,2-Dicyclohexyl-
butane
/ Vc-c-c-c
276to278 49 -"
0.9084 49 - 63
Dl*
1.500."
O
0.9104 ."
C,,H
210
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
Iff
;
Additional Data
1,4-Dicyclohexyl-
butane
Q-C-C-C-C-Q
9 68
304 to 306
294 M
@ 725mm
0.8772 M
.475
2-Methyl-l,l-dicyclo-
dP --00007 4 /C
hexylpropane
dt (0 to 15)
278 to 279 49 - 63
0.8906 "
1.492 49 - 63
Dl*
@15
0.9017 4fl - 63
c-c-c
II
Dl
1
c
O
2-Methyl-l ,3-dicyclo-
hexylpropane
c
290 to 292
0.8840 49 - 53
1.484 49 - 63
Ol / \
- C ~ C - C :<L/
Dl 9
0.8916 - B
19
Dl
211
C 17X1)1
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
iff
s
Additional Data
1,5-Dicyclohexyl-
^--oooos c
pentane
d<
/ Vc-(0 3 -o/ \
3 IS 25
0.8719 - 53
0.8836
1,47949,53
@21
1.478 25
@0
0.8832 4 - M
3-Methyl-l,l-dicyclo-
dD
hexylbutane
d ' (0 to 20)
290 to 291 < 9 - 63
0.8940 .
! >48 94,M
D! 1
@21
0.9058 49 - 63
c-c-c-c
Dl
1 1
o c
2-Ethyl-l,3-dicyclo-
dD
hexylpropane
dt (0 to 20)
c
296 ."
0.8846 ."
1.483 49 - 63
1
0J 1
@ 21
OK3
0.8966
212
Name and Carbon Skeleton
M. P.,*C.
B. P., C.
% 760mm
iff
-B
Additional Data
1,6-Dicyclohexyl-
hexane
o~o
212
@ 14mm
2,4,6-Trimethyl-l-(2,4,
6-trimethylcyclohexyl) -
cyclohexane
(2,4,6,2',4',6' Hexamethyl-
123 to 126 2
0.8932
1.4873*
dicyclohexyl)
@ 3mm
Dli
@25
C C
/ \
\ /
c c
1 ,8-Dicyclohexyloctane
O-*W~>
VV \/
26 !8
213
C to XI si
Name and Carbon Skeleton
M. P. t C.
B. P. t C.
760mm
Of
n-
Additional Data
Bis-(l-Methylr
4-isopropyl)-
cyclohexane
(Dimenthyl)
105.5 to
217 to 220 2
0.8925
106"
@40mm
^2?
195 to 197
0.891 1
@ 30mm
/; 2r
185 to 186 M
@ 21mm
199 to 202
@21mm
C24 H.46
5,8-Dicyclohexyldo-
decane
O(C) 3 -C-C-C-O (C) 8 -C
170 7
0.8823 7
66
@ 0.2mm
214
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
n D
Additional Data
1 ,1-Dicyclohexylhexa-
decane
18.5 to
269 to 27 1 32
0.8791
1.48620"
19.5 M
@ 15mm
@ 17.5
260 to 264
C-(C)ir-C
1
@ 10mm
O
1,3-Dicyclohexyl-
2-pentadecyl-
propane
( 1 -Cyclohexyl-2-hexa-
288 to 290 32
0.8860 32
t.4911 32
hydrobenzylheptadecane)
@ 17mm
@15
279 to 281 M
OrO
@ 10mm
(C), 4
1
c
3
1
ttj<)
<J
o ^
0.'
8 o
o
215
1
a
1
O
u
u
I
o
i-0
U
216
Name and Carbon Skeleton
M. P.,C.
B, P., C.
@ 760mm
i?r
B
Additional Data
Cycloheptylcyclo-
^--0.0006,rC.
heptane
* (0 to 20)
(Dicycloheptyl)
290 to 291 83
0.9069 3
290 to 29 1 36
Dl*
O-O
@ 728mm
0.9195 3
Cyclooctylcyclo-
octane
(Dicyclodctyl)
140
0.9277 47
1.5018 47
@ 1mm
0.9292 * 7
f^\ f*\
w W
@ 18.2
L Cyclopentadecylcyclo-
pentadecane
dD
_. _n nnn/w (
dt (85 to 100)
(Dicyclopentadecyl)
4447
0.866 < 7
1.4748 47
@100
100
0.8728 * 7
@ 88.6
217
(1) R. Adams and J. R. Marshall, J. Am. Chem. Soc. 50, 1970, 1928.
(2) H. Adkins, W. Zartman, and H. Cramer, J. Am. Chem. Soc. 53, 1425, 1931.
(3) K. Adier and H. Rickert, Ber. 71, 373, 1938,
(4) W. Borsch and W. Lange, Ber. 38, 2766, 1905.
(5) J. v. Braun, N. Durand, and C. S. Marvel, J. Am. Chem. Soc. 58, 1594, 1936.
(6) J. v. Braun, E. Kamp, and J. Kopp, Ber. 70, 1750, 1937.
(7) J. v. Braun and P. Kurtz, Ber. 70, 1224, 1937.
(8) J. S. Buck and W. Ide, J. Am. Chem. Soc. 53, 3510, 1931.
(9) J. Denissenko, Ber. 69, 1668, 1936.
(10) J. Denissenko, Ber. 69, 2183, 1936.
(11) J. Denissenko, J. Gen. Chem. (U.S.S.R.) 6 (68), 1263, 1936.
(12) E. B. Evans, J. Inst. Petr. Tech. 24, 537, 1938.
(13) J. Eykman, Chem. Weekblad 1, 7, 1903.
(14) D. Frederick, H. Cogan, and C. S. Marvel, J. Am. Chem. Soc. 56, 1815, 1934.
(15) P. Freundler, Compt. rend, 142, 343, 1906.
(16) J. Frezouls, Compt. rend. 155, 42, 1912.
(17) C. E. Garland and E. E. Reid, J. Am. Chem. Soc. 47, 2333, 1925.
(18) C. Hell and O. Schaal, Ber. 40, 4162, 1907.
(19) W. Huckel, O. Neunhoffer, A. Gercke and E. Frank, Ann. 477, 99, 1929.
(20) V. N. Ipatieff?Ber. 40, 1281, 1907.
(21) V. N. Ipatieff and B. Dolgov, Compt. rend. 185, 210, 1927.
(22) V. N. Ipatieff and V. I. Komarewsky, J. Am. Chem. Soc. 56, 1926, 1934.
(23) V. N. Ipatieff and N. Orlov, Compt. rend. 181, 793, 1925.
(24) V. N. Ipatieff and N. Orlov, Compt. rend. 183, 973, 1926.
(25) V. N. Ipatieff and N. Orlov, Compt. rend. 184, 751, 1927.
(26) P. Karrer, H. Salomon, R. Morf, and 0. Walker, Helv. Chim. Acta 15, 878, 1932.
(27) I. Kagehira, Bull. Chem. Soc. Japan 6, 241, 1931.
(28) R. Kuhn and A. Winterstein, Helv. Chim. Acta 11, 123, 1928.
(29) N. Kursanoff, Ann. 318, 327, 1901.
(30) N. Kursanoff, J. Russ. Phys. Chem. Soc. 34, 222, 1902.
(31) N. Kursanoff, J. Russ. Phys. Chem. Soc. 34, 224, 1902.
(32) S. Landa and J. Cch, Collection Czechoslov. Chem. Commun. 6, 423, 1934.
(33) J. Loevenich, H. Utsch, P. Moldrikx, and E. Shaefer, Ber. 62, 3084, 1929.
(34) A. Mailhe and M. Murat, Bull. soc. chim. [4] 7, 1083, 1910.
(35) Mascarelli and Vecchiatti, Atti R. Acad. dei Lincei Roma [5] 19, II, 410, 1910.
(36) W. Markownikow and L. Jakub, J. Russ. Phys. Chem. Soc. 34, 912, 1902.
(37) W. Meiser, Ber. 32, 2049, 1899.
(38) L. A. Mikeska, C. Smith, and E. Lieber, J. Org. Chem. 2, 499, 1938.
(39) S. S. Nametkin and L. Abakumowskaja, Ber. 66, 358, 1933.
(40) S. S. Nametkin and L. Abakumowskaja, J. Gen. Chem. (U.S.S.R.) 2, 608, 1932.
(41) S. S. Nametkin, L. Abakumowskaja and M. Rudenko, J. Gen. Chem. (U.S.S.R.) 7, (69), 763,
1937.
(42) C. Nenitzescu and E. Cioranescu, Ber. 69, 1820, 1936.
(43) A. Petrov and L. Angus, Ber. 66, 420, 1933.
(44) P. S. Pinkney and C. S. Marvel, J. Am. Chem, Soc. 59, 2669, 1937.
(45) P. S. Pinkney, G. A. Nesty, R. Wiley, and C. S. Marvel, J. Am. Chem. Soc. 58, 972, 1936.
(46) Ranendo and Leon, Anales soc. espan. Fis. Amin. 21, 270, 1923.
(47) L. Ruzicka and H. Boekenoogen, Helv. Chim. Acta 14, 1319, 1931.
(48) P. Sabatier and A. Mailhe, Compt. rend. 138, 1321, 1904.
(49) P. Sabatier and M. Murat, Ann. chim. [9] 4, 253, 1915.
(50) P. Sabatier and M. Murat, Compt. rend. 154, 1390, 1912.
(51) P. Sabatier and M. Murat, Compt. rend. 154, 1771, 1912.
(52) P. Sabatier and M, Murat, Compt. rend. 155, 385, 1912.
218
(53) P. Sabatier and M. Murat, Compt. rend. 156, 1431, 1951, 1913.
(54) J. Salkind and N. Schuwalow, J. Gen. Chem. (U.S.S.R) 7 (69), 1235, 1937.
(55) J. Schmidt and A. Segwart, Ber. 45, 1779, 1912.
(56) F. K. Signaigo and P. L. Cramer, J. Am. Chem. Soc. 55, 3326, 1933.
(57) R. Truffault, Compt. rend. 200, 406, 1935.
(58) A. Tschitschibabin and S. Jelgasin, J. Russ. Phys. Chem. Soc. 46, 812, 1914.
(59) O. Wallach, Ber. 40, 70, 1907.
(60) W. Zartman and H. Adkins, J. Am. Chem. Soc. 54, 1668, 1932.
(61) N. D. Zelinsky, Ber. 58, 2755, 1925.
(62) N. D. Zelinsky, S. Michlina, and M. Eventowa, Ber. 66, 1422, 1933.
(63) N. D. Zelinsky and N. Schuikin, J. Russ. Phys. Chem. Soc. 62, 1343, 1930.
(64) N. D. Zelinsky, N. Schuikin, and L. Fateev. J. Gen. Chem. U.S.S.R. 2, 671, 1932.
(65) N, D. Zelinsky and I. N. Titz, Ber. 64, 183, 1931.
(66) N. D. Zelinsky, I. N. Titz, and L. Fateev, Ber. 59, 2580, 1926.
(67) N. D. Zelinsky, I. N. Titz, and M. Gaverdovskaja, Ber. 59, 2590, 1926.
IV. TRI-, TETRA-, AND PENTACYCLANES, C n H 2n -4, C,,H 2n _ 6 , C ft H 2n _g
221
TRICYCLOPARAFFINS, C n H 2n ,_ 4 d,H 8 ,
^~1
*i* t*s
rS-a ?&*
^ <* . P g ^
I ^P 8
>^ JG w
JD o -^
13 -S-"-!
|B3 |ll'
2-
Q
ft
si
00
ON
O\
O
5 3 02 o|
S 3
45
OS
2 3
a
1
-9 jd
i P i
to
O
o
&r
to o\
44 cs
CO *>
a s
oo
*
S S
222
3
i;
o
o>
! f-O
to
f O
} 0-^-0
O
223
*" 3:
: vo
"
ON
O
224
C 8 ,H TETRACYCLOPARAFFINS, C.H, _,
CV| 00
ON *"
* a
8 1 3
3 oi ,2
o
Co
19
I yk
19
19
lo
?
I
1
5 a
+3 OO '
00 S
o X o
-M O 4J
ON 2 3
225
P
fr
1 o-o
a
o 8
C M H
226
I
oq
+
f
a
<3
<D
I
O
227
PENTACYCLOPARAFFINS, C n H 2 .. 8
I
X
PC)
$
T-t
ON
1
o
o
o
V. BICYCLANES OR BICYCLOPARAPFINS
1 . Bicyclanes with an alkyl substitution, CnH 2n -2
2. Bicyclanes with an alkenyl or olefm substitution, CnH 2n _4
3. Bicyclanes with two alkenyl or one alkadienyl substitution.
231
1. BICYCLANES OR BICYCLOPARAFFINS WITH
ALKYL SUBSTITUTIONS, C.H,._,
C,H 1(
Name and Carbon Skeleton
M. P.,C.
B. P M C.
@ 760mm
D?
n-
Additional Data
[0,l,3]-Bicyclo-
hexane
78 to 79.5 117
0.8144 117
1.4309 l17
@ 750mm
21.5
80 to 8 1 116
1.4320 " 7
@ 748mm
1.4337
17
[0,2,2]-Bicyclo-
hexane
78.5 to 79.5
@ 732mm
0.8245 86
1.4475 80
5,5-Dimethyl-
[0,l,3]^- 3 >-bicyclo-
hexane
c r^^Vi
115.2 to
0.8125 M
1.4385 98
115.4 98
0.7962 124
1.4331 124
c
115 124
114.0 to
fl8.
0.7929| ]24
fl23,
1.4329{ 124
114. 1 77
0.7976 12 *
@ 740mm
n 20
^20
232
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
s
Additional Data
2,2,4-Trimethyl-
[0,1,3^^-bicyclo-
hexane
c
137 to 138 4l
0.8223 39
1.4465 a ' J
Q<
138.5 to 139 a "
D?
@18.5
\
@ 759mm
140.5 39
c
@ 752mm
4-Methyl-l-isopropyl-
[0,l,3]<''>-bicyclo-
.*-
hexane
(Thujane)
158 to 159 lu
0.8143 18
1.440 18
(Tanacetane)
765mm
[)H
@26
C-C-C
157 to 160 22
157 to 158 22
0.8158 l8 - 91
1.4412lp
156 to 157 l8 - 19
0.8140"
22
155 to 156 18 - 19
1.43939"
157 38
0.8181 22 - 97
@20.2
1
C
@ 759mm
0.8139 97
1.4440 22
157 97
0.8171 38
.4435 19
@ 758mm
D?
.4410 19
156.2 to
0.8161 37
.4400 38
156.8 73
.4399 n4
@ 756mm
Do 20
.4398 37
156 to 157 91
@ 747mm
0.8142 70
@ 19.5
1.43759 97
{22
157.5 to 158 37
0.819022,97
97*
@ 741mm
@ 17
@ 17
0.8191 97
@16
1.44102"
0.8161 97
@ 16
1.43 70S 73
a
1.44495"
1 .44983 n
n H
7
233
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D?
3
Additional Data
[0,l,4]-Bicyclp-
heptane
(Norcarane)
111 to 112 12
0.8391 l2
1.4544 13
O
23
23
[l,2,2]-Bicyclo-
heptane
( Norbornylane)
86 to
CD
3743
2-Methyl-[l,2,2]<i.<).
bicycloheptane
c I
125 to
126.5
0.8532 113
@ 20.5
1.4535 ll3
@ 20.5
ItJ
@ 761mm
0.8561 113
1.4553 113
124.5 to
@ 16.5
@ 16.5
126
@ 745mm
II
121 to
0.8537 113
1.4545 113
123.5 m
@ 16.5
<& 16
@ 745mm
234
Name and Carbon Skeleton
M. P.,C.
B. P. t C.
760mm
iff
g
Additional Data
2,2-Dimethyl-[l,l,3]<.'>-
bicycloheptane
(Nopinane)
149 91
0.8611 M
1.46141
@ 747mm
Dll
@22
C
2,2-t>imethyl-[l, 2,2] <>-
bicycloheptane
(Camphenilane)
15 to
142 44
0.8547 64
1. 4555 M
16 64
142.5 64
0.8539 44
1.4534 44
C
Xf\<^
17 44
@ 753mm
L ? J c
2,3-Dimethyl-[l,2,2]<'. 4 >
bicycloheptane
( Dihy drosantene)
0.8712 10
1.4636 "
@ 18.5
@ 18.6
C
CK-
C
235
Name and Carbon Skeleton
M. P.C.
B. P., C.
760mm
Iff
w 20
Additional Data
7,7-Dimethyl-[l,2,2]-
bicycloheptane
(Apofenchane)
17 to
143.5 44
0.8538 44
1.45414**
17.5 44
C-C-C
CTT
10 **18
2,2,5-Trimethyl-
lJ =-34"
heptane
(Carane)
169.5 40
0.836 20
1.455 20
759mm
Dll
26
/c
165 to 166 91
0.8410 40
1.4551 114
O^
750mm
jfn
24
c
168 to
168.5 114
0.8381 91
D 20
f40,
1. 45823 j 1
@ 748.5mm
20
1.4573 114
162 20
19
@ 684mm
105 to 106 47
@ 116mm
49 to 50 91
@ 9mm
236
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
iff
s
Additional Data
2,2,4-Trimethyl-
K, 8 =+23.8-
heptane
[a]^- 4-23.08 .
(Pinane)
__ 45 u'j.ioo
166^
fl7,
(,
Wi>==+ 22.7 w ^
d form
166"
JM.
u.
1.4624J ,
c
@ 755mm
|"
85,
*Lipp 62 states that h<
163 to
164* 55,85,125
0.861 ". 100
L,
has determined tha
this is the cis isomei
k/x c
@ 720mm
D\l
of pinane. He alsc
1
states that the a\
C
compound is whal
Sabatier and Sen
derens 79 have iso
lated.
237 C H
Name and Carbon Skeleton
M. P.C
(fy 760tnin
iiT
;:
A dditiowl Data
2,2,4-Trimethyl-
lal^-1.25--
heptane
[a] D --9.58 0|
(Pinane)
- 50 "
168 to
0.8550 87
1.4620 S6 - 108
[1 I) =-13.3 CIW
/ form
168.5 109
@20.5
1.4605 109
166 85
0.8567 l
1.4601 i
[ot]^=-i6.r M . iofl
164.8 to
165.8 66 -
0.8562 "."
0.8542 09
1.4580 109
1.4540
[a]^-- 17.62 w
163. 5 to
0.8512 i 9
1.4648 107
[a] -18.9 M '"
165 1OT
758mm
0.8390
0.8607 107
1.4630"
[a] D ** -19.84
166"
20
/75\ in
755mm
163.5 to
165 109
0.8519 M ' 106
17.5
1.45952"
17.5
[a]g-- 20.55 l07
I] IJ --21.3 OM
750mm
168 to
0.8620 86
1.4595 10 *
@17.5
169 M
@ 748mm
167.5 to
168 109
@ 748mm
165.5 to
166 M
@, 721mm
162 to
164 55,108
@ 720mm
162 to 164 87
@ 7 19mm
164.8 to
165.8 1M
@ 716mm
238
Name and Carbon Skeleton
\/f P f
a. Jr., C.
B. P., C.
@ 760mm
z>r
B
Additional Data
2,2,4-Trimethyl-
heptane
(Pinane)
169tol70 118
0.8467 m
1.4605 114
Unspecified optical activity
@ 768mm
@21
@21
164.5 to
0.8558 8
1.4554 115
165"
0.8551 w
@21
@ 763mm
0.8521 lu
1.461 l w
166tol68 118
0.8430 M
1.4609 M
@ 752mm
0.8402 9
1.4572 M
165 to 169 M
@ 752mm
0.8453 l18
1.4559' 9
1.4589 115
165 to 169.5 M
@ 752mm
0.8470 115
18
168.5 1I6
@ 748mm
163.5 to 164 68
@ 747mm
167 to 167.5 114
@ 737mm
1,2,2-Trimethyl-
heptane
c
116 to
1 c
117 flfl
239
C 10 flu
Name and Carbon Skekton
M. P. t C
B. P., C.
@ 760mm
D?
n$
Additional Data
1,2,3-Trimethyl-
[1,2,2] <i.>-bicyclo-
heptane
( 1 -Methyldihydrosantene)
159 to 160 <
0.8520
C
f^lN/
C
/-1,3,3-Trimethyl-
[a] D =- 18.11
heptane
W fl --18 Q
(Fenchane)
151 to 152 44
0.8345 44
1. 44752 78
Mj,-- 16.53 38
@ 765mm
0.8337 7
1.447 14 44
C
151.5 38
0.83 1 7 62 - 66
1.4463 38
[aj^^- 15.22 72
xTv.
@ 763mm
0.8316"*
1.4462 104
II ^
145 to 147 76
0.8326 38
! .4459 62 ,65
\LX'\
149.2 to
/} 20
c
149.5 fl2 ' 66
@ 753mm
0.8471 2
149 104
o
@ 750mm
149 to 149.3 47
@ 749mm
240
Name and Carbon Skeleton
M. P.?C.
B. P., C.
(rf)/ 760mm
D?
%
A
d-l,3,3-Trimethyl-
[!,2,2]<' 4 >-bicyclo-
heptane
(d-/--Fenchane)
161 to 163 42
0.861 2
1.46152 42
@ 755mm
1.45921
1.46741 42
1. 46740 42
nf f
<fM,3,3-Trimethyi-
heptane
(d-/-|8-Fenchane)
158 to 160
0.8553 42
1 45744 42
@ 752mm
1.455 II 42
1. 46304 42
1. 47208 42
2,2,3-Trimethyl-
[1,2,2] < l 4 >-bicyclo-
heptane
M D
(Isocamphane)
d form
62 to
63 64
166 to 166.5 M
61.5 to
rtYc
63 M
c
idditional Data
241
io XI 18
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
Iff
8
Additional Data
2,2,3-Trimethyl-
M fl =-8.5
[l,2,2]<i.-bicyclo-
heptane
/ form
63 to
164"
64.5 64
@>, 757mm
2,2,3-Trimethyl-
[l,2,2]<M>4>icyclo-
heptane
optical activity unspecified
65 to
163 64
0.82757 "
1. 44186 M
66 64
164.5 M
@67
@67
60 to
@ 709mm
1.43982"
61 108
n a
a
1.45239"
;
V
1,4,7-Trimethyl-
heptane
(4-Methylsantenane)
152 to 154
0.8531 4fl
C
1
1
C
242
Name and Carbon Skeleton
M. P./T.
D o/^
/5. X^., C.
< 76()mm
D?
"8
Additional Data
1,7,7-Trimethyl-
[l,2,2]<'*>-bicyclo-
heptane
(Camphane)
145 < 8
160 to 161 38
0.7458 48
153 to
@ 763mm
@ 152
C
{96,
1.
160 to 161 "
161 to 162 21
lc xC I
156 to
161 W ' 1W
M^ .
fl04,
Itfju.
@ 757mm
157 to
158"
158 to
159"
151 4
151 to
152
ISO 21
2,7,7-Trimethyl-
[l,2,2]< l ' 4 >-bicyclo-
heptane
[1 4 1 1/C Rfi
alj, 53 ~ 12,5o B6
[] .-8.16i
(Isobornylane)
163,5 to
0.8579 w
1.4590 65
C
164.5 "
@ 753mm
fl08,
0.8566J 1U
1.4577 114
1.4560 108
r x t^i /
162 to
1.4559 1 "
\c'*? J
163.5 114
(& 19 5
SJX
@ 753mm
162.5 to
163.5 1M
@ 751mm
243
Name and Carbon Skeleton
AI. P. t n C.
B. P., 9 C.
(m 760mm
Iff
;
Additional Data
1 ,2,7,7-Tetramethyl-
heptane (?)
(Methylcamphane)
C
1 c
138 to
139 w - 7
170 to
@ 752mm
0.81 60 6
1. 46235 M
l,7,7-Trimethyl-2-
propyHl,2,2]<>.<>-
bicycloheptane
(2-Propylcamphane)
C
| c-c-c
32 to
32.5
223 to 223.5 70
l,7,7-Trimethyl-4-
propyHl,2,2]<>.<>-
bicycloheptane
(4-Propylcamphane)
C
32 to
32.5 70
223 to 223.5 70
1
C-C-C
244
Name and Carbon Skeleton
M. P.,C.
@ 760mm
DT
s
Additional Data
[0,3,3]-Bicyclooctane
cis
127 to 135 ll2
0.8241 *
1.447 1 112
CO
[0,3,3]-Bicyclo6ctane
trans
-30 <
132 4
0.8626
1.4625
($ 762mm
@ 18
18
0.867
1.4651 4
@U
14
[l,2,3]-Bicyclooctane
0)
141 2
[2,2,2]-Bicyclooctane
f^N
168"
II
16$ to
170 *
245
Name and Carbon Skeleton
M. P.,C.
B, P., C.
@ 760mm
tit
<
Additional Data
[0,x,x]-Bicyclooctane
139.5 to
0.8604 1M
1. 46148 l03
140.5 1W
0.8775 103
l-Methyl-[2,2,2] <><>-
bicyclooctane
c
1
149 to 151 89
0.875 80
1.46900*
2-Methyl-[2,2,2].<>-
bicyclooctane
c
33 to
157 to 158.5 3
0.8674 36
1.4613*
S\^./
3436
@ 760.8mm
@40.5
@40.5
246
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
Iff
s
Additional Data
3,7-Dimethyl-
[0,3,3] < '*>-bicycloSctane
-CO-
165 to 167 "
0.8341 3
24
1.4481 34
5,5-DimeihyHl, 2^] <*>-
bicyclooctane
(Dihydroendocamphene)
171.5 to 173"
0.87706 M
1. 46847 N
^Tx
@ 17.4
@ 17.4
GD
C C
[0,3 ,4]-Bicyclononane
0.881g
1.471 4
= 0.00064/C.
(10 to 20)
(Hydrindane)
166 80
0.8783 29
1.4683 12
cis
166 120
@25.1
1.4716 30
/X^^x
@ 758mm
0.8815 30
1.4714 3 o
1 I/
166 29
@ 20.7
1.4713 30
^sS^S
@ 734mm
0.880 30
1.47270 30
0,879 30
@16.8
0.8849 M
1. 47500 30
@15.3
@ 12
0.8872 80
1. 46897 29
247
Name and Carbon Skeleton
M p r
JxL, JT.| v/.
B. P., C.
@ 760mm
tif
B
Additional Data
[0,3,4]-Bicyclononne
[al w --10.8*
/ trans
159 30
0.8630
1.4655 4
156*
0.865 4
@ 18.2
@ 747mm
dl tram
159 to 160 80
0.863
1.4643 86
158 "
0.8645 30
1.46630*
@ 18.3
n 14 - 6
[0,3 ,4]-Bicyclononane
(Hydrindane)
165 to 166 83
0.8284 l8
1. 46897 4
with no specification of
@ 767mm
@81.2
24.9
cis and trans forms
163.5 to
0.8759 lfl
1.4696 118
164.5 "
@23
1. 46287 3S
166 to
0.8334 83
1.4711 m
167 28 - 118
0.8790 ul
@15.5
@15.5
1.4750 4 - 28
0.8872 28
cis-1-Methyl-
[0,3,4] o,5)-bicyclo-
nonane
(8-Methyl hydrindane)
12 to
69 @ 19mm 14
0.8778 4
1.4707"
13 "
56
@16
@16
C
@ 10.5mm
0.8754
1.4699
O>
@ 13.5
@ 13.5
CioH.it
248
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D?
^
Additional Data
l-MethyHO,3,4]<'.>>-
bicyclononane
(8-Methyl hydrindane)
159 to 160 7
80 to 82 6
(& 50mm
2-Methyl-[0,3,4]<i.'>-
bicyclononane
(1 -Methyl hydrindane)
182 to 183 7 '
0.8763 71
1. 46934 7l
C
00
2-Methyl-3-isopropyl-
[0,3,4]^-bicyclononane
c
127 to 137"
0.8715 "
1.4660 11
^x\jl
@28mm
1 | \-c-c
249
Name and Carbon Skeleton
Mp r
. JT 4, lx.
B. P., C.
@ 760mm
/)!
5J
Additional Data
l-Methyl-[l,3,3]<'.*>-
bicyclononane
c
176 to 178 n
0.8416 77
1.4529 77
1
@ 751mm
l,3-Dimethyl-[l,3,3]<i >-
bicyclononane
c
195 to 200 78
1
@ 750mm
/ fj \ , X-N
CTT
13*124
9-Methyl-3-isopropyl-
bicyclononane
rTA
232 to 233 79
0.8643 7ft
1.4660 79
/c-c y-c-c
@ 755mm
c
132 7
@ 28mm
250
Name and Carbon Skeleton
U. P.,C.
B. P., C.
@ 760mm
Iff
<
Additional Data
[0,4,4]-Bicyclodecane
0.895 y
1.480,
(Decahydronaphthalene)
-43.26
193"
0.898 24
1.4773
(Decalin)
31,98
@ 768mm
0.8963 M
@22.5
-45 2
190.4 to
0.8962 81
1.4823 M
CIS
CO
191.2 8
@ 764mm
190.2 to
190.4 M
@ 763mm
193.8 8l
0.8957 13
0.8953 "
[26,
0.8952j na
0.8951 8
1.481 13 w
1.48054"
1. 48035 3
@ 763mm
0.895 27
1.4803 81
194.6 w
0.8838 76
1.4741 76
193 18,26,110,111
0.8805 76
1. 48279 26
192 to 193.6 122
0.8986
@ 19
.~ J Q
1.4815 120
189 to 191
(^17.5
188 to 192 75
1.47789 3
187 to 188
w //
186 to 190 76
a
1.48638 3
188.5 to
190.5 l02
ff fl
@ 717mm
1.49154 8
@ 12mm
1. 48068 "
68 to 70 8l
W 20
@ 12mm
251
Name and Carbon Skeleton
M. P. t C.
B. P., *C.
760mm
fiT
H D
Additional Data
[0,4,4]-Bicyclodecane
1.469.
(trans)
- 31.47
185 13
0.8641 S6
1.4871 m
-33 2 '
@ 765mm
@30
@ 20.5
-36 26
187 to 188 49
0.87 14 121
1.4713 24 - 2i
186 to
@21
1. 46968
186.5 m
0.8704 122
1.4696 119
185
@21
1.46958
184 to
0.8715 26
1.4695 27 - n
186.5 m
@ 20.5
1.4691 M
182 to 184.5 75
185.5 W
0.8823 18
0.8820 13
1.4675 *
1.46994 27
185 l3
0.87 7
@ 18.2
@ 756mm
0.872
1.47225 M
63 2I
0.8709 2
@ 18
@ 12mm
0.8699
1.46720
62 to 63 81
0.8695 26
W 55
@ 12mm
0.8667
a
1.46728 27
0.8657 75
n-' 2
0.8734 26
1.47572 27
0.8703 27
" l l
@ 18.2
1.48727 M
0.8783 2
wg
@10
1.48060"
0.893 49
W 18.2
@o
y
1.47461
w 20
1.47442"
C 10 HIS
252
Name and Carbon Skeleton
M. P. t C.
B. P., C.
760mm
Iff
S
Additional Data
[0,4,4]-Bicyclodecane
cis and trans
185 to 193 M
0.8609 "
1.4965 16
188 to 191
@50
23
191.6 1
0.9134
1.4750 "
195 to 196
@23
1.4753 86
189 to 191 36
0.8881 w
1.4771 84
189 to 190 74
0.884 "
1.4773 15
0.8833
15
0.8781 4
Cll JUL20
ciVl-Methyl-[0,4,4]<i.>-
bicyclodecane
c
82 @ llmm 24
0.8909 24
1.4813 24
r^T^i
79 llmm 63
16.1
16.1
kJkJ
0.8994 63
1.4844 68
^N-^ ^NX^
12.5
12.5
frans-1-Methyl-
[0,4,4] o 6 >-bicyclodecane
75 @ 14mm 81
0.8633
1.4631"
70 to 71 8l
0.8583 8l
1.4702 81
@ 12mm
0.8654 2 *
17.6
17.6
1.4697 M
17.6
253
Name and Carbon Skeleton
\r D O/* 1
M. Jr., L.
B. P., C.
@ 760mm
D?
nj
Additional Data
l-Methyl-[0,4,4]c' : >-
bicyclodecane
(Mixture of cis and trans
isomers)
0.892 M
1.481
2-Methyl-[0,4,4]a.>-
bicyclodecane
c
GO
205 lot
0.885 101
frans-3-Methyl-
0,4,4] ('.^-bicyclodecane
CO'
78 @ 14mm
76 @ 12mm 81
0.8670 81
1.4681 81
3-Methyl-[0,4,4]-
bicyclodecane
201 lfll
0.876 101
^20
254
Name and Carbon Skeleton
M. P.,C.
B, P., C.
@ 760mm
Iff
w z>
Additional Data
2-EthyHO,4,4]<">-
bicyclodecane
c-c
222 fij
0.8843 6l
1.4764"
CO
@23
0.8985 6l
3-Ethyl-[0,4,4]<M>-
bicyclodecane
c-c
222 M
0.8763 M ."
1.4746."
r XSs Y xx i //
221 w
@ 13.2
@ 13.2
^XX^NX^
92 @ 13mm 60
0.8857
cf*s-l,5-Dimethyl-
[0,4,4] < l ->-bicyclo-
decane
c
85 ."
0.8896
1.4812 - 82
l^^k^^
@ 12mm
0.8847 M
1.4787 53
L JL J
84 to 85 M
@16
@ 16
^^^^ II
@ 10mm
c
255
~D T) O/^
Name and Carbon Skeleton
M. P.,C.
@ 760mtn
/;5
W 2
Additional fiala
trans-1 ,5-Dimethyl-
[0,4,4] <M>-bicyclo-
decane
77 to 78 81
0.8633 81
L4659 81
@ 12mm
0.8544 M
1.4658"
76 to 78 M
@ 15
@ 15
% 10mm
1
2,8-Dimethyl-
[0,4,4] < l 6 >-bicyclo-
decane
c
1
f xX \T'X\)
218
0.880 lfll
/\x\/
c
3,8-Dimethyl-
[0,4,4] u^-bicyclo-
decane
c
216 to 217
0.872 i
S^Y^^ //
208 l
I
/ \x\x^
c
256
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
s
Additional Data
3,9-Dimethyl-
[0,4,4] <i.)-bicyclo-
decane
c c
216 to 218
0.851 8 119
XXT
cis-l-Methyl-4-
M55-~o.85 8
ethyl-[0,4,4] <*>-
bicyclodecane
c
-112^8
102 to 103 82
0.8912 88
1.4819 82
rXXixx^
@ 12mm
0.8903 82
1.481 1 83
III
101 to 102 83
^>v^^ ^\
@ 12mm
c-c
<rans-l-Methyl-4-
ethyl-[0,4,4]<'.>-
bicyclodecane
97 to 98 81
0.8630 81
1.4665 81
@ 12mm
257
Name and Carbon Skeleton
1/f D o/'*
M. f. t G.
B. P., C.
% 760mm
Iff
s
Additional Data
cis-l,5-Dimethyl-8-
ethyl-[0,4,4](">-
bicyclodecane
c
115 to 116 82
0.8904 82
1.4815 82
nr^i
@ 12mm
c-c |
c
1 ,5-Dimethyl-8-ethyl-
[0,4,4]-bicyclodecane
112 to 113 8l
0.8703 81
1.4727 81
@ 14mm
l,5-Dimethyl-8-ethyl-
[0,4,4] <M>-bicyclo-
decane
(1,4(a)-Dimethyl-7-
120 to 125 s
ethyldecalin)
@ 20mm
H^i
/UJ
c-c I
c
258
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760inm
7)5 *
s
Additional Data
2-Ethyl-3-propyl-
[0,4,4] < l .>-bicyclo-
decane
c-c
1 c-c-c
ca
79 to 89 72
@ 2mm
0.8839 72
1.4778 72
1 ,5-Dimethyl-8-iso-
propyl-10,4,4]^ fl) - .
bicyclodecane
[]= + 10.2 '<
c
126 to 128 M
0.8896 M
1.48471 w
M D =+1 V "
x^XiX^
10.5mm
0.8893 M
1.483 M
/^^^^
c-c |
1 c
c
122 to 122.5 *
@ 7.5mm
116 to 117 M
@ 6.5mm
0.8881 M
0.891 1 8 *
1. 48278 4
1. 48259 N
2 ,8-Dimethyl-5-iso-
propyHO,4,4]<'- 6 >-
bicyclodecane
H.--
(Tetrahydrocadinene)
125 to 128
@ 10mm
0.8838 w
1.4805
C
i^V^i
/CO
c 1
c-c-c
259
Name, and Carbon Skeleton
M. P.,(\
B. P., C.
@ 760mm
//;"
"S
Additional Duta
2,9-Dimethyl-5-iso-
H tf -H4.6""
propyl-[0,4,4] <'>-
bicyclodecane*
*Correct structure of
(Tetrahydroisozingiberet?e)
123 to 123.5 90
0.8822
1.479 1 90
this seems to be 2,8-
Dimethyl-5-iso-p r o -
@ 10mm
ovl-fO 4 41^ 1|8 ^-bic v-
C
C |
clodecane. See Sim-
\-XXXX.
onsen, "The Ter-
penes," p. 498. Cam-
\x\/
bridge Press, Lon-
\
don (1932).
c-c-c
C 17 H 32
2-Propyl-3-butyl-
[0,4,4] (1 ^-bicyclo-
decane
c-c-c
98 to 100 72
0.8796 "
1. 4790 72
I c-c-c-c
@ 2mm
CO"
2,2-Dimethyl-9-(l,5-
dimethylhexyl)-
[0,4,4] >-bicyclo-
decane
(Hexahydroiso-a-
180 to 186 92
0.8588
1.46800"
camphorene)
@ 14mm
21
C C
T>1x o3
M "8<
260
Name and Carbon Skeleton
M. P.C.
p p o/*
z>. -r., C.
@ 760mm
Iff
-8
Additional Data
3-Octadecyl-[0,4,4] <>-
bicyclodecane
0-(C),r-C
43 to
0.863 55>
1.4739 69
r x ^V xx i /
47 69.60
@25
@25
oo
(extrap.)
(extrap.)
3-DocosyHO,4,4]<' >-
bicyclodecane
C~(C) 2 o-C
0.8673 5
1.4759 69
or
@25
3-(2-Butyloctadecyl)-
[0,4,4] ( 1 ')-bicyclo-
decane
c
240 to 245 60
0.8615 59
1.4772"
1
@ 3mm
@25
25
(C) 3
1
C~C-(C)i5-C
or
261
(1) K. Alder and G. Stein, Ann. 514, 1, 1934.
(2) K. Alder and E. Windemuth, Ber. 71, 2404, 1938.
(3) K. v. Auwers, Ber. 46, 2988, 1913.
(4) J. W. Barrett arid R. P. Linstead, J. Chem. Soc. 1935, 1069.
(5) C. Chuang, Chi Ming Ma, Yu-Lin Tien, Ber. 68, 1946, 1935.
(6) Clemmensen through W. Hiickel, Ann. 441, 1, 1925.
(7) G. Clemo and H. Dickerson, J. Chem. Soc. 1935, 735.
(8) G. Clemo and R. Haworth, J. Chem. Soc. 1930, 2579.
(9) E. Coulson, J. Chem. Soc. 1935, 77.
(10) E. Deussen, J. prakt. Chem. [21 114, 63, 1926.
(11) M. Djakowa and A. Petrov. J. Gen. Chem. (U.S.S.R.), 3, 679, 1933.
(12) P. Ebel, R. Brunner, and P. Mangelli, Helv. Chem. Acta 12, 19, 1929.
(13) F. Eisenlohr and R. Polenske, Ber. 57, 1639, 1924.
(14) K. D. Errington and R. P. Linstead, J. Chem. Soc. 1938, 666.
(15) E. Evans, J. Inst. Petr. Tech. 24, 537, 1938.
(16) J. Eykman, Chem. Weekblad 3, 685, 1906.
(17) Fokin and Wilistatter through A. Lipp, Ber. 56, 2098, 1923.
(18) P. Guha and S. Krishnamurthy, Ber. 70, 2112, 1937.
(19) P. Guha and B. Nath, Ber. 70, 931, 1937.
(20) P. Guha and D. Sankaran, Ber. 71, 2673, 1938.
(21) G. Henderson and E. Pollock, J. Chem. Soc. 97, 1620, 1910.
(22) G. Henderson and A. Robertson, J. Chem. Soc. 123, 1713, 1929.
(23) A. Hesse, Ber. 39, 1127, 1906.
(24) D. C. Hibbit and R. P. Linstead, J. Chem. Soc. 1936, 470.
(25) W. Huckel, Ann. 441, 1, 1925.
(26) W. Huckel, Ann. 533, 1, 1937.
(27) W. Huckel, Ber. 58, 1449, 1925.
(28) W. Huckel and H. Friedrich, Ann. 451, 132, 1926.
(29) W. Huckel and E. Goth, Ber. 67, 2104, 1934.
(30) W. Huckel, M. Sachs, J. Yantschulewitsch, and F. Nerdel, Ann. 518, 155, 1935.
(31) W. Huckel, K. Kumetat, and H. Severin, Ann. 517, 184, (1935).
(32) V. N. Ipatieff, Ber. 40, 1281, 1907.
(33) V. N. Ipatieff, J. Russ. Phys. Chem. Soc. 45, 994, 1913.
(34) R. L. Jones and R. P. Linstead, J. Chem. Soc. 1936, 616.
(35) I. Kagehira, Bull. Soc. Chem. Japan 6, 241, 1931.
(36) B. A. Kazansky and A. F. Plate, Ber. 68, 1259, 1935.
(37) N. Kishner, J. Russ. Phys. Chem. Soc. 42, 1203, 1910.
(38) N. Kishner, J. Russ. Phys. Chem. Soc. 43, 586, 1911.
(39) N. Kishner, J. Russ. Phys. Chem. Soc. 44, 853, 1912.
(40) N. Kishner and Sawadowski, J. Russ, Phys. Chem. Soc. 43, 1137, 1911.
(41) G. Komppa, Ber. 68, 1267, 1935.
(42) G. Komppa and S. Beckmann, Ann. 508, 205, 1934.
(43) G. Komppa and S. Beckmann, Ann. 512, 172, 1934.
(44) G. Komppa and T. Hasselstrdm, Ann. 496, 164, 1932.
(45) G. Komppa, T. Him, W. Rohrmann, and S. Beckmann, Ann. 521, 242, 1936.
(46) G. Komppa and G. A. Nyman, Ann. 517, 105, 1935.
(47) D. Kursanoff, J. Gen. Chem. (U.S.S.R.) 4 (66), 598, 1934.
(48) M. Leffler and R. Adams, J. Am. Chem. Soc. 58, 1555, 1936.
(49) H. Leroux, Compt. rend. 139, 672, 1904; Ann. chim. [8] 21, 468, 1910.
(50) G. Levy, Compt. rend. 192, 1397, 1931.
(51) G. Levy, Compt. rend. 193, 174, 1931.
(52) G. Levy, Ann. chim. 9, 1, 1938.
262
(53) R. P. Linstead, R. Millidge, and A. Walpole, J. Chem. Soc. 1937, 1140.
(54) P. Lipp, Ann. 382, 265, 1911.
(55) A. Lipp, Her. 56, 2098, 1923.
(56) P. Lipp, A. Gotzen, and F. Reinartz, Ann. 453, 1, 1927.
(57) H. Meerwein and K. van Emster, Ber. 53, 1815, 1920.
(58) Miehr, Diss. Munich, (1913), Quoted by A. Lipp, Ber. 56, 2098, 1923.
(59) L. A. Mikeska, Ind. Eng. Chem. 28, 970, 1936.
(60) L. A. Mikeska, C. F. Smith, and E. Lieber, J. Org. Chem. 2, 499, 1938.
(61) S. S. Nametkin, J. Russ. Phys. Chem. Soc. 47, 410, 1915.
(62) S. S. Nametkin, J. Russ. Phys. Chem. Soc. 47, 1596, 1915.
(63) S. S. Nametkin, J. Russ. Phys. Chem. Soc. 51, 150, 1919.
(64) S, S. Nametkin, Ann. 438, 186, 1924.
(65) S. S. Nametkin, L. Abakumowsky, and A. Seliwanoff, Ann. 440, 60, 1924.
(66) S. S. Nametkin and L. Brussowa, J. Russ. Phys. Chem. Soc. 55, 525, 1923.
(67) S. S. Nametkin and L. Brussowa, Ann. 459, 144, 1927.
(68) S. S. Nametkin and A. Jarsev, Ber. 56, 832, 1923.
(69) S, S. Nametkin and A. Jarsev, J. Russ. Phys. Chem. Soc. 54, 77, 1922.
(70) S. S. Nametkin and A. Schawrigin, Ann. 516, 199, 1935.
(71) C. Nenitzescu and C. Cioranescu, Ber. 69, 1040, 1936.
(72) G. A. Nesty and C. S. Marvel, J. Am. Chem. Soc. 59, 2662, 1937.
(73) G. Ostling, J. Chem. Soc. 101, 468, 1912.
(74) L. Palfray, Compt. rend. 206, 1976, 1938.
(75) E. Prokopetz, J. Applied Chem. (U.S.S.R.) 8, 1214, 1935.
(76) W. Quist, Ann. 417, 278, 1918.
(77) P. Rabe, Ber. 37, 1671, 1904.
(78) P. Rabe and M. Jahr, Ann. 360, 265, 1908.
(79) P. Rabe and K. Weilinger, Ber. 37, 1667, 1904.
(80) W. Roth and K. v. Auwers, Ann. 407, 145, 1914.
(81) L. Ruzicka, D. R. Koolhaas, and A. H. Wind, Helv. Chim. Acta. 14, 1151, 1931.
(82) L. Ruzicka, D. R. Koolhaas, and A. H. Wind, Helv. Chim. Acta, 14, 1171, 1931.
(83) L. Ruzicka and P. Pieth, Helv. Chim. Acta, 14, 1090, 1931.
(84) P. Sabatier and A. Mailhe*, Ann. chim. phys. [8] 10, 527, 1907.
(85) P. Sabatier and J. Senderens, Compt. rend. 132, 1254, 1901.
(86) M. Sachs, Diss. Gottingen, 1928.
(87) Schenk, Diss. Munich, (1910), quoted by A. Lipp, Ber. 56, 2098, 1923.
(88) W. Schrauth and T. Battler, Deutsche Hydrierwerke, A-G. Ger. 663, 963, Aug. 1938.
(89) F. W. Semmler and K. Bartelt, Ber. 40, 4846, 1907.
(90) F. W. Semmler and A. Becker, Ber. 46, 1814, 1913.
(91) F. W. Semmler and J. Feldstein, Ber. 47, 384, 1914.
(92) F. W. Semmler and K. G. Jonas, Ber. 47, 2068, 1914.
(93) F. W. Semmler and F. Risse, Ber. 45, 3301, 1912.
(94) F. W. Semmler and F. Risse, Ber. 46, 2303, 1913.
(95) W. Seyer and R. Walker, J. Am. Chem. Soc. 60, 2125, 1938.
(96) J. L. Simonsen, "The Terpenes," vol. 2, p. 222, University Press, Cambridge, 1932.
(97) L. Tschugaev and W. Fomin, Compt. rend. 151, 1058, 1910.
(98) A. E. Uspensky, J. Russ. Phys. Chem. Soc. 51, 259, 1920.
(99) G. Vavon, Compt. rend. 149, 997, 1909.
(100) G. Vavon, Compt. rend. 150, 1123, 1910.
(101) G. Weissenberger, R. Henke, and H. Katschinka, Z. anorg. allg. Chem. 153, 33, 1926.
(102) R. Willstatter and D. Hatt, Ber. 45, 1471, 1912.
(103) R. Willstatter and T. Kametaka, Ber. 41, 1485, 1908.
(104) L. Wolff, Ann. 394, 95, 1911.
263
(105) L. Wolff, G. Weiland, and E. Thielepape, Ann. 297, 92, 1912.
(106) Wdllmer, Diss. Munich, (1913), quoted by A. Lipp, Ber. 56, 2098, 1923.
(107) Zacharewicz, Bull. Inst. Pin [3] 1935, 143.
(108) N. D. Zelinsky, J. Russ. Phys. Chem. Soc. 36, 768, 1904.
(109) N. D. Zelinsky, Ber. 44, 2784, 1911.
(110) N. D. Zelinsky, Ber. 57, 2062, 1924.
(111) N. D. Zelinsky and P. Borissow, Ber. 57, 2060, 1924.
(112) N. D. Zelinsky and M. Friemann, Ber. 63, 1485, 1930.
(113) N. D. Zelinsky, B. A. Kazansky, and A. F. Plate, Ber. 66, 1415, 1933.
(114) N. D. Zelinsky and R. Levina, Ann. 476, 60, 1929.
(115) N. D. Zelinsky and R. Levina, Ber. 62, 339, 1929.
(116) N. D. Zelinsky, S. E. Michlina, and M. Eventowa, Ber. 66, 1422, 1933.
(117) N. D. Zelinsky and M. Ouchakoff, Bull. soc. chim. [4] 35, 484, 1924.
(118) N. D. Zelinsky and I. N. Titz, Ber. 62, 2869, 1929.
(119) N. D. Zelinsky, I. N. Titz, and L. Fatejev, Ber. 59, 2580, 1926.
(120) N. D. Zelinsky and M. B. Turova-Pollak, Ber. 62, 1658, 1929.
(121) N. D. Zelinsky and M. B, Turova-Pollak, Ber. 65, 1299, 1932.
(122) N. D. Zelinsky and M. B. Turova-Pollak, Ber. 58, 1292, 1925.
(123) N. D. Zelinsky and A. E. Uspensky, Ber. 46, 1466, 1913.
(124) N. D. Zelinsky and A. E. Uspensky, J. Russ. Phys. Chem. Soc. 45, 834, 1913.
(125) Zwanziger, Diss. Munich, (1917), quoted by A. Lipp, Ber. 56, 2098, 1923.
C..H,, 264
2. BICYCLANES WITH AN ALKENYL OR OLEFIN SUBSTITUTION, C.H
Name and Carbon Skeleton
i(jf p r
JXL -* *-'
B. P., C.
760mm
iff
-8
Additional Data
d-4-Methylene-l-iso-
propyl-[0,l,3]<i.>-
bicyclohexane
[ a ] D = +80.17 60 ' 64
(Sabinene)
163 to
0.8430 *
1.4660 36
[ a ] D = 4- 80.07
155 50,54,64
@30
@30
OC-C
162 to 166 48
0.840 48 - 54
1.465 60
163 to 165 4
0.842 ""
1.466 48
@ 757.6mm
0.8422 4
1.4678 64
66
@ 17
1. 46738 4
II
@ 30mm
(^ 17
c
My
1. 46428 4
1.47514 *
1.48196*
7
J-4-Methylene-l-iso-
propyl-[0,l,3]< l .*>-
bicyclohexane
WS-42J-
162 to 166
0.8407 *
1.465 60
161. 5 to 163 60
Z>3 8 J
@30
@ 705mm
0.8468 '
265
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
*3
Additional Data
3-Methylene-2,2-di-
methyl-[l,2,2]<i.>-bi-
0.845
50
[]g=+ 103.89 *
cycloheptane
[]g- +74.55
(d-Camphene)
42.7 53
160 to
0.8446 3
1.45641 3
43 to
161 36,59,68
50
50
f xTx/ C
43.5 3
158 to
0.8450 3fl
1.4581 60
I J
46 to
158.5
50
48
^sU^\
473
157 41
0.8456 7
1.4533 7
c
46 36
157.6 53
50
25
48 41
745mm
0.8486 3
1.4570 88
48 to
157.2 to
50
25
4959
159.9 3
0.850 60
1. 46048 3
50 7 - 68
@ 742mm
48
H H\
160 to
51.2 21
!62 ".so
739.9mm
0.854 7
W5--95.7
40
[ajg= 92.37 16
/-Camphene
39 68
160 to 161 8
0.8062
1. 45085 8
4432
159 to 160 18
97.7
63
fa]J5=~80.7 2
45 to
48 15 - 41
158.5 to
159.5 6
0.82 II 41
79.7
1.455 14
Hg-51.88
4920
50"
158.5 to
159 32
0.83473
63.4
1. 46207 e*
40
[]j>=- 84.9 fi8
51 to
156 to 157 41
0.8387 41
[J =~80 66
52
158 to 158.8 4
58.9
D
55 B6
759mm
0.84224
=* -0.0008 5 /C.
157.8 20
54
dt (40 to 100)
743mm
0.8481 41
dn 00004 C
47.7
dt (40 to 65)
0.8555 M
40
266
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
nl
Additional Data
3-Methylene-2,2-di-
methyl-[l,2,2]<'.<>-bi-
cycloheptane
(Continued)
^/-Camphene
41 to 42 2
160 to 161 *
0.8223 13
1.44115 >3
44.5 to
160 18
@78
W ^
46
159.5 to
0.8524
1.45061 13
45 to
160 2 - 19
n 60
^60
n 76
4630
46 to
159 to 160
158 to
0.8544 38
n 56
^65
H R
1. 45614 13
n 7 *
472
160 30 - M
0.8565 M
48 to
158tol59 2 . lfi
49 2,16
4910
157 to 157.5 **
@ 750mm
0.8586 38
49 to 51 2
49.5 to
156.3 to
156.7 31
D\l
0.8609
50.5 2
@ 712mm
n 40
i/IO
506,31,54
51 to 53 37
54 18
@ 17mm
d-5-Methylene-2,2-di-
methyl-[l,2,2]ci.<>-
bicycloheptane
[a\ D = +62.91 3
(,3-Fenchene)
151 to 153 28
0.8591 39
1.4645 39
c
150.5 to
0.8599 39
@23
153.5 39
1.4654 39
CD
150 to 153 39
@ 18.6
c
267
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
ng
Additional Data
5-Methylene-2 ,2-di-
methyl-11,2,2]" <>-bi-
cycloheptane
151 to
0.8581 2
1.4644"
153 23 - 27 > 28
0.8596 27
1.465 II 24
152 to 153 2 <
0.8597 24
1.4658 27
0.8598
1.4662 28
@17
@17
M-Methylene-7,7-di-
[jg-- 17.19 47
methyHl,l,3]<'.*>-
bicycloheptane
[a] D = -22.48 n
(Nopinene, 0-Pinene)
About
165.2
0.866 67
1.4647"
[a^-- 22.33 fl7
-50 87
164 to 166 47
@22
@22
f^Tcl
164
0.869 46 - 54
1.4724"
[],,-- 22.1
l^xl
163 to 165 54
0.8708 "
@22
014
][
162 to 164 4
0.8650 "
1.4766 70
W/) 558 -
c
162 to 163 w
15
@ 20.5
(aj =-17.8 04 ' 64
160 fll
0.8720 47
1.47548"
"
156 to 157 61
@15
0.8740 12
1.4812 n
1.478 s
[a^-- 16.24'"
164 to 166 I4
@ 15
@ 758mm
0.875 8
1.4872 12
163.5 to
15
@15
165. 5 70
@, 742mm
0.8758 81
Dl
268
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
B
Additional Data
2-Methylene-7,7-di-
I-t 32J-
bicycloheptane
[]= -32.76 3
(/-a-Fenchene)
159 to 162"
0.8616
1. 47092
[a]g= -32.12 69
157 to 159
0.865 "
@23.2
C
x .
156 to 157 M
0.8664 39
1. 46876 w
la] D --4.4 M
[c-c-cl
155 to 160 25
0.8675 39
@22.3
W
155 to 158'-' 9
0.8677 29
1.4642 33
a i>-
154 to 156 ft:)
0.869 9
1.47085 39
[]. -- 39.50 29
@ 19.5
u
153 to 155.5 35>
@ 19
152 to 157 33
0.866 Lo
1.4724"
@1 Q
@ 750mm
0.867
19
153 to 154 "
@18
1.4693 03
@i oo
@ 720mm
0.8670
lo
@ 17.5
1.46729*
@i 7 eo
0.870
i / .0
@13
1.4750 44
2-Methylene-7,7-di-
WJ-+12.76 "
methyl-[l,2,2]<>.<>-
bicycloheptane
(rf-a-Fenchene)
155 to 161 66
0.8630 66
1.4699"
140.5 to
142.5 39
@ 755mm
2-Methylene-7,7-di-
methyHl,2,2]<'.<>-
bicycloheptane
tffo-Feochene)
158 to 160
0.8660
1.47045
154 to 156
0.8656
1.4708
155 to 157
0.864 *
1.46900
269
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Of
S
Additional Data
2,2-Dimethyl-3-*thyli-
dene-[l ,2,2] <* .<>-bicyclo~
heptane
H.-+08-
(w-Methylcamphene)
178 30
0.8638 "
1.4643 71
172 to 173 7l
@27
27
f^T^<^ c
@ 743mm
0.884 to
f? 1 c
0.888 SQ
C-C
2-Methylene-l ,3,3-tri-
methyl-[l,2,2]".>-
bicycloheptane
(<a-M ethylcamphene)
170.5 to 171 34
C
1 c
@ 764mm
C
3-Methylene-l ,7,7-tri-
methyl-[l, 2,2] <i.-
bicycloheptane
(Methyl enecamphane)
28 fl5
166 to 168 w
C
1
58 to 62
@ llmm
fc-c-cj
c
270
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D?
s
Additional Data
<5-Methylene-5,7,7-tri-
methyl-[l, 1,3] <'*>-
bicycloheptane
lag =+0.2420"
(Methylpinene)
161 to 164 17
0.8363 l7
1.46362
C
@ 783mm
C
2-Methylene-l ,5,5-tri-
methyl-[l,2,2]<i.<>-
bicycloheptane
(<f/-Methyl-/3-fenchene)
160 to 162
0.85205
1.46261 22
@ 20.5
C
C
3-Methylene-2,2-di-
methyl-1-propyl-
[aJa--36.71*
heptane
(j8-Propylcamphene)
92 to 93
0.87188
1.4786
C-C-C
@ 16mm
86 to 87
0.8722
1.4770"
(Tj<
@ 12mm
C
271
Cull*
Name and Carbon Skeleton
M. JVC.
B. P., C.
(^ 760mm
;,f
nj
Additional Data
l,7,7-Trimethyl r 6-(3-
methylbuten-3-yl)-
l] fl =-29.4r 9
heptane
(-y-Dihydrocaryophyllene)
126 10
0.8872 9
1.4880 9
C
c=c~c-c |
@ 15mm
124 to 124,5 9
@ 12.75mm
13 1 50
@21
0.8893 10
@18
0.8965 60
1.4885 10
@18
1.496 60
@ llmm
@18
frans-8-Methylene-
[0,3,4]-bicyclononane
(/rans-2-Methylenehexa-
hydrohydrindene)
59 to 60 "
@ 9.5mm
0.8663 "
1.4720 62
frans-3-Methylene-
[0,4,4]-bicyclodecane
(/raw$-2-Methylenedecalin)
82 to 82.5 82
@ 10mm
0.8897 4fl
0.8928 M
1.487052,55
ay
81 to 83
272
Name and Carbon Skekton
M. P.,C.
B. P., C.
760mm
iff
"5
Additional Data
1 ,5-Dimethyl-8-isopro-
periyl-[0,4,4]-bicyclo-
W~7-
decane
(Dihydroeudesmene)
132 to 133 46
0.9067 4fl
1.4876 49
@ 15mm
0.9075 45
1.4972
C
127"
0.9080
1.5043 48
j j'^ 1
@ 12mm
x\x\/
126 to 127 < 5
oc |
@ 12mm
c
126 to 130 49
(a) 10mm
7-Methylene-l-methyl-
4-isopropyl-[0,4,4]-
bicyclodecane
( Dihydroselinene)
138tol39 46
0.8992
1.4878 tt
@ 12mm
24
@24
C
f^^4^^
II c-c
c 1
c
273
(1) J. AKIICW and R. Croad, Analyst, 37, 2<)5, 1912.
(2) O. Aschan, Ann. 383, 39, 191 L
(3) O. Aschan, Ann. 398, 299, 1913.
(4) K. v. Auwers, W: Roth, and F. Eisenlohr, Ann. 373, 267, 1910.
(5) J. Bertram and H. Walbaum, J. prakt. Chcm. [2] 49, 15, 1894.
(6) J. Briihl, Ber. 25, 142, 1892.
(7) J. Bruhl, Ber. 25, 162, 1892.
(8) M. Darmois, Ann. chim. [8] 22, 527, 1911.
(9) E. Deussen, J. prakt. Chem. [2] 90, 318, 1914.
(10) E. Deussen, J. prakt. Chem. [2] 114, 63, 1926.
(11) G. Dupont, private communication (Beilstein, suppl. Vol. 5, p. 77).
(12) G. Dupont and L. Desalbres, Bull. soc. chim. [4] 33, 1252, 1923.
(13) J. F. Eykman, Chem. Weekblad, 3, 701, 1906.
(14) E. Gildemeister, W. Muller through 0. Wallach, "Festschrifte" 1909, 416.
(15) Golubew, J. Russ. Phys. Chem. Soc. 41, 1004, 1909.
(16) C. Harries and J. Palmer, Ber. 43, 1432, 1910.
(17) T. Hasselstrom, Ann. Acad. Sci. Fennicae 30A, No. 11, 13.
(18) G. Henderson and E. Pollock, J. Chem. Soc. 97, 1620, 1910.
(19) W. Htickel, K. Kumetat, and H. Severin, Ann. 518, 184, 1935.
(20) W. Huckel and W. Tappe, Ber. 69, 2769, 1936.
(21) J. Kachler and F. Spitzer, Ann. 200, 340, 1880.
(22) G. Komppa, Ann. 472, 179, 1929.
(23) G. Komppa and S. Beckmann, Ann. 508, 205, 1934.
(24) G. Komppa and T. Hasselstrom, Ann. Acad. Sci. Fennicae 26A, No. 1, 3, 1927.
(25) G. Komppa and R. Roschier, Ann. 470, 129, 1929.
(26) G. Komppa and R. Roschier, Ann. Acad. Sci. Fennicae 1916A, 3.
(27) G. Komppa and R. Roschier, Ann. Acad. Sci. Fennicae, Ser. A X, 15, 1, 1917.
(28) G. Komppa and R. Roschier, Ann. Acad. Sci. Fennicae, Ser. A VTI, 14, 1, 1917.
(29) J. Kondakow, J. prakt. Chem. [2] 75, 539, 1907.
(30) G. Langlois, Ann. chim. [9] 12, 193, 1919.
(31) P. Lipp, Ann. 382, 265, 1911.
(32) P. Lipp, Ann. 399, 241, 1913.
(33) S. S. Nametkin, L. Abakumoswky, and A. SeliwanofT, Ann. 440, 66, 1924.
(34) S. S. Nametkin and A. Churchrikova, J. Russ. Phys. Chem. Soc. 50, 254, 1918.
(35) S. S. Nametkin and A. Schawrigin, Ann. 516, 199, 1935.
(36) R. Padmanabhan and S. Kulkarni Jatkar, J. Am. Chem. Soc. 57, 334, 1935.
(37) M. Pariselle, Compt. rend. 176, 1901, 1923.
(38) W. H. Perkin, Sr., J. Chem. Soc. 81, 292, 1902.
(39) W. Quist, Ann. 417, 278, 1918.
(40) A. Reychler, Bull. soc. chim. [3] 15, 366, 1896.
(41) J. Riban, Ann. chim. [5] 6, 353, 1875.
(42) H. Rupe and J. firm, Helv. Chim. Acta 7, 546, 1924.
(43) L. Ruzicka and E. Capato, Ann. 453, 62, 1927.
(44) L. Ruzicka and F. Liebl, Helv. Chim. Acta 6, 267, 1923.
(45) L. Ruzicka, A. H. Wind, and D. R. Koolhaas, Helv. Chim. Acta 14, 1132, 1931.
(46) H. Schmidt, Z. angew. Chem. 42, 126, 1929.
(47) A. Schorger, J. Am. Chem. Soc. 35, 1896, 1913.
(48) F. W. Semmler, Ber. 33, 1455, 1900.
(49) F. W, Semmler and E. Tobias, Ber. 46, 2026, 1913.
(50) J. L. Simonsen, "The Terpenes," Vol. 2, p. 520, Cambridge University Press.
(51) K. Slawinsky and J. Piliczewski, Roczniki Chem. 11, 763, 1931.
(52) R. Tudor and A. Vogel, J. Chem. Soc. 1934, 1250.
(53) D. Tsakalotos and B. Popoconslantinow, J. Pharm. et Chim. [7] 14, 97, 1916.
274
(54) W. Treibs and H. Schmidt, Ber. 61, 459, 1928.
(55) R. Thakur, J. Chem. Soc. 1932, 2120.
(56) G. Vavon, Compt. rend. 149, 997, 1909.
(57) G. Vavon, Compt. rend. 150, 1127, 1910.
(58) G. Wagner and W. Brickner, Ber, 32, 2302, 1899.
(59) O. Wallach, Ann. 230, 234, 1885.
(60) O. Wallach, Ann. 245, 191, 1888.
(61) O. Wallach, Ann. 246, 221, 1888.
(62) O. Wallach, Ann. 263, 129, 1891.
(63) O. Wallach, Ann. 300, 294, 1898.
(64) O. Wallach, Ann. 350, 141, 1906.
(65) O. Wallach, Ann. 353, 224, 1907.
(66) O. Wallach, Ann. 357, 49, 1907.
(67) O. Wallach, Ann. 363, 1, 1908.
(68) O. Wallach and P. Gutmann, Ann. 357, 79, 1907.
(69) 0. Wallach and P. Vivck, Ann. 362, 174, 1908.
(70) N. D. Zelinsky and R. Y. Levina, Ber. 62, 339, 1929.
(71) N. D, Zelinsky and J. Zelikow, Ber. 34, 3249, 1901.
275
3. BICYCLANES WITH TWO ALKENYL OR ONE ALKADIENYL
SUBSTITUTION, C,H 8 .., C lt H 18
Name and Carbon Skeleton
M. P.C.
B. P., C.
@ 760mm
DT
<
Additional Data
2 ,2-Dimethyl-3-pro-
pen-2-ylidene-[ 1 ,2 ,2]-
(i ,4>-bicycloheptane
[aJ^-4- 76.39
(w-Vinylcamphene)
203 to 205 l
0.917 *
85 to 90 >
0.921
r^TV
@ 10mm
@15
f A J\c
MA,
c-c=c
C 13X120
2 ,2-Dimethyl-3-buten-
2-ylidene-[l,2,2]<i.*>-bi-
cycloheptane
[ a ] z> = s +70i
( n> - Propeny Icamphene)
230 to 232 l
0.919 !
95 to 97 *
@ 15
^[^/ C
@ 12mm
c l^c
c-c=c-c
2 , 2-Dimethyl-3-penten-
2-ylidene-[l,2,2]< J *>-
bicycloheptane
H ^.
(w-Butenylcamphene)
238 to 240 l
0.905 *
110 to 120 '
@15
fT^C
@ 15mm
^J/\,
c-c=c-oc
276
Name and Carbon Skeleton
M, P.,C.
B. P., C.
@ 760nim
Iff
W'
Additional Data
2 ,2-Dimethyl~3-hexen-
2-ylidene-[l,2,2]<M>-bi-
M^+73.5 04
cycloheptane
(>-Pentenylcamphene)
255 l
0.900
r^i< c
140 @ 10mm
15
c-c=c-c-c-c
l-Methyl-7-meth-
ylene-4-isopropenyl-
[0,4,4]<. ) -bicyclode-
\
W^ = -f 31.36 5
cane
[^=+49.5*
(/3-Selinene)
268 to 272 4
0.9107 6
1.50311 5
142 to 144 3
0.9140 2
1.5042 2
|J ) =+63 8
C
@ 20mm
0.9196 4
1.5102 3
1 1^ 1
136 to 139 fi
0.9232 *
@15
^X^xXx C
@ 17mm
(5), 15
II C
135 2
0.9279 *
c \
c
@ 16mm
15
(1) G. Langlois, Ann. chim. [9] 12, 193, 1919.
(2) L. Ruzicka, J. Meyer, and M, Mingazzini, Helv. Chim. Acta 5, 345, 1922.
<3) L. Ruzicka, A. H. Wind, and D, R. Koolhaas, Helv. Chim. Acta, 14, 1132, 1931.
<4) Schimmel and Co., Geschaftsbericht, April, 1910.
<5) F. W. Semmler and F. Risse, Ber. 45, 3301, 1912.
VI. TRICYCLANES, (ENDOCYCLIC), C n H 2n _ 4
279
VI. TRICYCLANES, (ENDOCYCLIC), C.H,
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Df
g
Additional Data
2 ,2-Dimethyl- 1 ,4-endo-
methylene-[0,l ,3] (3 - 5) -bi-
cyclohexane
(Apocyclene)
36.5 to
138 to 139 31
0.8710 81
1.45 144 31
37.5 28
@ 764mm
@40
@40
C
38.5 to
138 to 139.5 28
0.8717^
1.45204 OT
1 c |\
39.5 27
@ 763.7mm
@40
@40
^Jx c
39 to
138 to 139
0.8734
1. 45434 2
40 39
@ 762mm
@40
@40
41 to
137.5
1.44910 31
42 28
@ 756mm
H H
a
42.5 to
43 31
136.5 to 137 39
@ 748mm
1. 45686 31
H
P
1.46190 31
l,2,2-Trimethyl-l,4-
endomethylene-
[0,1,3] < 3 6 >-bicyclohexane
c
116 to
150 to 151 30
^L/ C
117 30
280
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
,r
B
Additional Data
2,2,4-Trimethyl-l,4-
0.859 8
[]- 4-3.54-0
endomethylene-
[0,l,3] (3 '*>-bicyclohexane
!];- i.77 u "
(Cyclofenchene)
143 to 143.7 60
0.8589
1.4503*
|a]^=+0.8 U6
@ 777mm
@ 20.4
@22
c
144"
0.8574 2fl
1.45212"
[aj=~0.28 06C
r^^ix
@ 770mm
0.8584 60
@ 20.4
LjJ c
144 to 146 4
0.8587 80
1. 45442"
[a] I) = 4-0.28 2
i
142.8 to 147 60
0.8588 32
@ 20.2
c
141.5 to
0.8591 60
1. 44769 2
143.5 2
0.8599 3
1.45133"
140 to 143 29
0.8603 40
1.4515 *
143 to 144 32
@ 756mm
0.8604 62
0.8609 44
1.4525"
1.4532"
141. 5 to 142 60
@ 755mm
143 to
143.5 40 - 41
0.8636 38
0.8624 1 - 32
@ 16.5
1.45327"
1.45768 3
1.4579"
@ 754mm
0.8624 4fl
1. 45364 L'
142 to 143 16 - 32
@ 16.4
j
@1 f\ "s
@ 752mm
143.6 to
0.8624 32
16
1O.O
1.45370"
@ 16.2
143.9 45
@ 750mm
1.45474 32
143 e2
O lo
@ 749.5mm
1.4547"
143 to 143.5 46
@16
@ 748mm
1.45104"
^- 2
143 to 143.5 44
@ 747.5mm
1.4523 1 82
145 to 149 38
n ii
a
@ 747mm
1.45968"
1.46067"
1.46449"
7716.2
1.46547"
M 16
n a
V
281
C 10 Hie
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
g
Additional Data
l-Methyl-l,4-(di-
methylendomethylene)-
[0,l,3] (3 ' 6 >-bicyclohexane
(Isocyclene)
117.5 18
150 to 151 43
0.7948 18 - 16
1. 40996
(iS-Bornylene)
117to
150 to 152 7
@ 120.8
n m.t
118 7
151 40
1.41743 18
?
11940.43
150 to 151 40
n Hp
r^T^i
150 to 151 68
1.42195 ' 8
c-c-c
@ 743mm
n m.B
i
2,2,3-Trimethyl-
1 ,4-endomethylene-
[0,l,3]< 3 ' 5) -bicyclohexane
(Tricyclene)
64 to
153 46
0.8268 18
1.43890*
(Cyclene)
65 29
@ 761mm
@802
@70
64.3 36
153.5 3fl - 37
0.8373 3 ' 37
1.44055"
C
64.5 to
153 to
@70
@ 66.9
1 c I ^
65 w
153.5 67
0.8440 46
1.42963 18
xXx'y c
65 3 36 - 37
152.3
@66.0
11/1 a
c
65.5 to
to 153.3 3B
1.43816"
66 41
152 to 152.5 59
W 68.9
66.5 17
66.5 to
152.8 to 153 60
@ 757.5mm
1.43744"
67 69
152.5 17 - 46
"a
67 to
@ 747mm
1.44644"
68 13
152
W M.9
67.5 to
@ 740 mm
1.44206"
67.8 60
W W).2
7
C n HH
282
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
DT
B
Additional Data
1 ,2 ,2 ,3-Tetramethyl-
1 ,4-endomethylene-
[0,1 ,3] (3 6 >-bicyclohexane
(4-Methyltricyclene)
109 to
163.5 to
HO 80
164.5 30
C
j
113 to
114
c
2,2,3,4-Tetramethyl-
1 ,4-endomethylene-
[0,l,3]< 3 .-bicyclohexane
.c
1 c ]\c
71 to
738
172 to 175 8
1 N
1 c
c
283
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
iff
8
Additional Data
2,5-Endomethylene-
[0,3 ,4]-bicyclononane
(low melting isomer)
916
191.5 18
0.9121 lfl
1.46705"
@ 769mm
@80
tt$- 2
a
Ouu
0.9027 17
79.2
1.49308"
?? 20.8
v-^xlx^
0.9492 "
a
@ 20.8
1.47538"
W 3' f
1.50184"
wJJ- 8
1.48021 l7
wg- 2
y
1.50706"
n 5; 8
(high melting isomer)
79 U,M
193 16
0.9120 ie
1.47258 ' 7
769mm
80
W 7?
a
123 16
0.9128 "
1.48101 "
100mm
79
118"
H s
@85mm
1.48592"
wJJ
101"
@48mm
86 16
@24mm
2,5-Endomethylene-
[0,4,4]-bicyclodecane
(1 ,4-Endomethylene
91 @ 22mm
decalin)
84 to 85
s^^^
@ 15mm
284
Name and Carbon Skeleton
M. P. f C
ft ft <>/
ID, Jr,, C,
@ 760mm
Iff
<*
Additional Data
2 ,5-Endoethylene-
[0,4,4]-bicyclodecane
f XX T x ? s l
0.9675 6
1.5042*
L JL c J
@22
@22
1.5015
Decahydroacenaph-
thene
r\
235 to 237 28
0.9488 2B
1.4996 28
r"VS
235 to 236 3 *
@25
@25
CO
235 21
230 to 234 23
0.9370 23
@o
4,5-Cyclopentano-
[0,3 ,4]-bicyclononane
/ v
106 to 108 47
0.9145 47
1.4840 47
C><3
@ 18mm
2,3-Cyclopentano-
[0,4,4]-bicyclodecane
(1,2-Cyclopentano-
decahydronaphthalene)
f^^r^Y
\x x \x'^
71 to 72 8
@ 2.5mm
0.9241 **
1.4895
285
Name and Carbon Skeleton
M. r., n c.
7*. P., C.
(?; 760mm
,*
ng
Add il ion a I Data
7,8-Cyclohexano-
[0,3 ,4]-bicyclononane
(Dodecahydrofluorene)
254 to 258 23
0.9496 23
CA3
24
2 ,3-Cyclohexano-
[0,4,4]-bicyclodecane
(Perhydrophenanthrene)
_ 3 34
270 to 275 34
275 to 276 "
0.9630 25
1.S003 11
25
XX
754.3mm
0.9609 25
1.5261 34
1 J
274 to 277 H
25
25
r' X " x Y x ^ x r
@ 739mm
156"
0.9385 48
0.9437 48
1.5323 34
25
Xx^xx^
@ 26mm
0.9447 48
1 .4994 48
147 to 149 14
0.933 34
1.501 1 48
@20mm
D*l
1.5019 48
150 to 160 26
@ 18mm
142 to 144 14
@ 15mm
135 16
0.9503
t.5035 14
1.50S0 1 *
1.5060"
16
@13mm
13 1 16
@ 10mm
93 to 96 48
@2.5mm
90 to 93 48
@ 2.5mm
86 to 89
@ 2mm
Cl4
286
Name and Carbon Skeleton
Af. P.,C.
B. P., C.
@ 760mm
/
-s
Additional Data
3 ,4-Cyclohexano-
[0,4,4]-bicyclodecane
( Perhy droan thracene)
60.5 to
272 to 277 *
0.9747 25
1.5275 M
^~^ ..
61
270 20
@25
@25
r^iiiii
61 to
ca. 270 M
69 10
^\x x ^v/ X ^s/ x ^
u*
150 to 155
88 to
@ 13mm
89 *
128
831,*0,M,35
@ llmm
90 to
90.5
0322
3,8-Dimethyl-2,5-(di-
WS-+2 "
methylendomethylene)-
[0,4,4]-bicyclodecane
W^- +33.10 w
( Dihy drocedrene)
118 to 124
0.9041 ia
1.48719 l2
@ 12mm
0.907 12
1.48721 52
C
122 to 123
0.9204"
1.4882 12
1 l-vl
@ 10mm
0.9247
1.49204 M
/^xX^xix^
116 to 122"
0.9052 w
1.4929 64
C
@ 10mm
109 to 112 i 2
@10mm
119 to 120
@8mm
287
Name and Carbon Skeleton
M. P.,C.
@ 760mm
DT
*s
Additional Data
2-Methyl-8-isopropyl-
M0-+18.08 04 "
2 ,3- (4-methylcyclo-
hexano) -[0,4,4]- bicycle
|aj ;) =r-f 19.00 w
decane
(Fichtelite)
46^
355
46.5
355.2
r^^i
48"
@ 719mm
^^ C N! I
235.6*
1 | T c
@ 43mm
v JL s
233.6
S ^x/'^^sX''^
s ^
c-c
1
@42mm
1
c
C 20 H36
1 ,3-Dimethyl-7-iso-
|aJj{=4-10.59 w M
propyl-2,3-(3-methyl-
cyclohexano ) -[0,4,4]-
bicyclodecane
(Tctrahydrosciadopitene)
175 to 176 w
0.9751
1.5278 B8
@ 6mm
15
C
170 to 171"
0.9761 ^
/~\Jx\X
I T \ c
@5mm
D u
^^^^^^
c-c-c
288
(1) D. Adelson and M. T. Bo^crt, diem. Rev. 24, 135, 1939.
(2) O. Aschan, Ann, 387, 1, 1912.
(3) O. Aschan, Bcr. 40, 2750, 1907.
(4) O. Aschan, Ber. 40, 4918, 1907.
(5) E. Bamberger and L. Strasser, Ber. 22, 3361, 1889.
(6) H. Bode, Ber. 70, 1167, 1937.
(7) J. Bredt and W. Holz, J. prakt. Chem. [2] 95, 133, 1917.
(8) J. Bredt and M. Savelsberg, J. prakt. Chem. [2] 98, 97, 1918.
(9) C. Bromeis, Ann. 37, 304, 1865.
(10) J. Brown, H. Durand, and C. S. Marvel, J. Am. Chem. Soc. 58, 1594, 1936.
(11) Y. I. Denissenko and W. M. Kotelnikowa, J. Gen. Chem OJ.S.S.R.) 7, 2819, 1937. '
(12) E. Deussen, F. Weiss, P. Hacker, and P. Hille, J. prakt. Chem. [2] 117, 273, 1927.
(13) O. Diels and K. Aider, Ann. 460, 98, 1928.
(14) J. Durland and H. Adkins, J. Am. Chem. Soc. 59, 135, 1937.
(15) J. Durland and H. Adkins, J. Am. Chem. Soc. 60, 1501, 1938.
(16) J. F. Eykman, Chem. Weekblad 1, 7, 1903.
(17) J. F. Eykman, Chem. Weekblad 3, 685, 1906.
(18) J. F, Eykman, Chem. Weekblad 3, 701, 1906.
(19) M, Godchot, Ann. chim. [8] 12, 468, 1907.
(20) M. Godchot, Bull soc. chim. [4] 1, 724, 1907.
(21) M, N. Goswami, Compt. rend. 179. 1269, 1924.
(22) E. Hulle, A. Gluschke, G. Stiar, and H. Miiller, Ber. 57, 1990, 1924.
(23) V. N. Tpatieff, Ber. 42, 2092, 1909.
(24) V. N. IpaliefT, W. Jakowlev, and L. Rakitin, Ber. 41, 996, 1908.
(25) I. Kagehira, Bull. Chem. Soc. Japan, 6, 241, 1931.
(26) G. Roller and H. Rues, Mh. Chem. 70, 54, 1937.
(27) G. Komppa and T. Hasselstrom, Ann. acad. sci. Fennicae 26A, No. 1, 3, 1927.
(28) G. Komppa and T. Hasselstrom, Ann. 497, 116, 1932.
(29) G. Komppa and T. Hasselstrom, Ann. 502, 272, 1933.
(30) G. Komppa and G. A. Nyman, Ber. 69, 334, 1936.
(31) G. Komppa and R. Roschier, Ann. 429, 175, 1922.
(32) G. Komppa and R. Roschier, Ann. 470, 129, 1929.
(33) S. Landa and V. Machacek, Collection Czechoslov. Chem. Commun. 5, 1, 1933,
(34) C. Liebermann and L. Spiegel, Ber. 22, 779, 1889.
(35) L. Lucas, Ber. 21, 2510, 1888.
(36) H. Meerwein and K. van Emstcr, Ber. 53, 1815, 1920.
(3>) S. J. Michlina, Wiss. Ber. Moskau, 3, 209, 1934.
(38) S. S. Nametkin, J, prakt. Chem. [2], 106, 25, 1923.
(39) S. S. Nametkin and Z. Alexandrow, J. Russ. Phys. Chem. Soc. 57, 382, 1926.
(40) S. S. Nametkin and L. Brussova, Ann. 459, 144, 1927.
(41) S. S. Nametkin and L. Brussova, J. prakt. Chem. [2] 112, 169, 1926.
(42) S. S. Nametkin and L. Brussova, J. prakt. Chem. [2] 135, 155, 1932.
(43) S. S, Nametkin and L. Brussova, J. Russ. Phys. Chem. Soc. 62, 333, 1930.
(44) S. S. Nametkin and A. Sseliwanowa, J. Russ. Phys. Chem. Soc. 49, 423, 1918.
(45) G. Ostling, Dissertation, Helinsgfors, 1911.
(46) G. Ostling, J. Chem. Soc., 101, 468, 1912.
(47) P. S. Pinkney and C. S. Marvel, J. Am. Chem. Soc. 59, 2669, 1937.
'48) P. S. Pinkney, G. A. Nesty, R. H. Wiley, and C. S. Marvel, J. Am. Chem. Soc. 58, 972, 1936.
(49) F. Plzak and V. Posicky, Z. Kryst. Mineral. 44, 339, 1908.
(50) W. Quist, Ann. 417, 278, 1918.
(51) J. Schmidt and R. Mezger, Ber. 40, 4240, 1907.
(52) F. W. Semmler and A. Hoffman, Ber. 40, 3521, 1907.
(53) F. W. Semmler and K. Spornitz, Ber. 47, 1029, 1914.
289
(54) J. L. Simonsen, "The Terpenes," Vol. 2, p. 536, University of Cambridge Press, London, 1932.
(55) L. Spiegel, Ber. 22, 3369, 1889.
(56) H. Staudinger and H. Rheiner, Helv. Chim. Acta 7, 23, 1924.
(57) L. Tschugaeff arid W. Budrick, Ann. 388, 280, 1912.
(58) H. Uota, J. Dept. Agr. Kyushu Imp. Univ. 5, 117, 1937.
(59) G. Wagner and J. Godlewski, J. Russ. Phys. Chem. Soc. 29, 121, 1897.
(60) G. Wagner, S. Moycho, and F. Zienkowski, Ber. 37, 1032, 1904.
(61) P. Walden, Chem. Z. 30, 391, 1906.
(62) N. D. Zelinsky and R. Y. Levina, Ann. 476, 60, 1929.
VII. POLYCYCLANES OR POLYCYCLOPARAFFINS
1. Polycyclanes with alkyl substitutions, C n H 2 n-
2. Polycyclanes with an alkenyl or olefin substitution, C n H 2 n-8
293
1. POLYCYCLANES OR POLYCYCLOPARAFFINS WITH ALKYL
SUBSTITUTIONS, C n H 2n _ 6 C 1
H 2
I
a
00
(N
i 6
S 6
O J
i
I
I
294
5
3
1
i
: I
! ?
si
s
7 s
1 10
V 3
I
^T
rp
cT
$
S
6
*-<
oT
"i
^
295
i
Ct> **3 .P
S 14
!|i :
I i!
^(5
0\
stS
10 ft
oo
*' 2
ft 10
3 3 CN
to oo c?\
CN VO *-
s; s:
296
ON
ON
i
O
i
06
6
to ^. yj
00 ^
o
o
297
CflH.40
a
CflH.44
5
<$
298
fe 6 c3
4-
rlj co
o eo
cs TH
* n
^ o
oo oo
S a
oo *-*
1
I
I
C/3
I
u
299
I
I
1
o>
5
300
s
5
O
o
ftn'
1
. 2
,101
302
2. POLYCYCLANES WITH AN ALKENYL OR OLEFIN
SUBSTITUTION, C.H,.^
Name and Carbon Skeleton
Af. P. t C.
B. P., C.
@ 760mm
Iff
w 20
Additional Data
Ledene
c
255*
0.9233 *
1.50273
C \/N^V /
264
0.9237
1,5050 4
c C Xx
@ 752mm
@ 19
^
139 to 142 4
0.9349 8
s
c
@ 10mm
@0
a-Santalene
r'Tv' ?
253 to 254
0.9132 6
1.49205 6
c ^c-c-c=c-c
252
@ 753mm
118 6
@15
0.9134 J
@o
@15
\u^\
c
@ 7mm
Longifolene
(a\ D =-f 42.73 '
C \ c
254 to 256 7
0.9284 7
1.495 7
c JX|N <l c _ c
@ 706mm
p;
@30
1 ^""^J?
150 to 151 7
c
@ 36mm
(1) M. Guerbet, Compt. rend, 130, 1324, 1900.
(2) E. Hjelt, Ber, 28, 3087, 1895.
(3) G. Komppa, Kgl. Norske Videnskab Selskabs, Skrifter 1933, 1.
(4) K. Ono, Mem. Coll. Sci. Kyoto, 8, [A], 1, 1925,
(5) Rizza, J. Russ. Phys. Chem. Soc. 19, 324, 1887.
(6) Schimmel and Co., Oct. 1910, 106.
(7) J. L. Simonsen, J. Chem. Soc. 117, 570, 1920.
VIII. CYCLENES OR CYCLOOLEFINS
1. Cyclenes with alkyl substitutions, C n Hg n _2
2. Cyclenes with an alkenyl or olefin substitution, C n H 2n -4
3. Cyclenes with two alkenyl or one alkadienyl substitution, C n H 2 n-6
4. Cyclenes with an alkene-alkyne or an alkatriene substitution, CnH" 2 ,,_ 8
305
1. CYCLENES WITH ALKYL SUBSTITUTIONS, C.H
In-S
C,H.
Name and Carbon Skeleton
K/f P C
VI, JT , vx.
B. P., C.
@ 760mm
,r
s
Additional Data
Cyclobutene
O
1.5 to 2
@ 729mm
0.733 *
C 6 H 8
1-Methylcyclobutene-l
c
37 to 39 2 - 3
0.7075 8
1.4034 2
i
37 to 38
@23
@23
@ 750mm
(1) A. Favorsky and V. Batalin, J. Russ, Phys. Chem. Soc. 46, 726, 1914.
(2) O. Philipow, J. Russ. Phys. Chem. Soc. 45, 1464, 1913.
(3) O. Philipow, J. prakt. Chem. 93, 162, 1916.
(4) R. Wfflstatter and J. Bruce, Ber. 40, 3979, 1907.
C t H,
306
Name and Carbon Skeleton
M. P.C.
T> T) Of
/5 / .j C* .
(m 760mm
iff
"5
Additional Data
Cyclopentene
44.4
0.772,
1.422 4
^= -0.0009 6 /C.
44 to 45
0.7716"
1. 42246 u
(5 to 20)
763mm
0.7736 61
1.4247 2
^=-00005 4 /C
44.3
0.776 2
1.4420"
di (5 to 20)
@ 761mm
0.7743 M
1.42183"
45 to 46 *
18
18
45 24,25
0.7753
1.42080"
44.02
17.9
14
43.6 to 43.8 2
0.7756"
1.4256 26 ' 27
44.1 to 44.6 60
17.2
13.5
@ 752mm
0.7754 81
1.4287"
43 to 44.2
14
10
@ 751mm
0.7783
1. 43052
T^13.5
7.1
0.7776 23
1.42818
10
n *l
0.7861 2
1. 43746 2
7.1
0.7864 2
P
6.75
1.44306 2
-v;
1-Methyl-
75.1
0.778
cyclopentene-1
dt (0 to 25)
c
-127.2"
75.5 to 76 l6
0.7754
1.4347"
1
75 to 76 13
n 23
^20
15
rs
72 to 75 6
0.7474 2
1.4309*-"
Y_J
72
21
13.5
754mm
0.7758
1.4319"
71 H
z>!
nl u
@ 743mm
0.791826,27
1.4416"
n !3.5
-t/18.5
n H
0.7979 "
1.4512"
@0
n 1&
H
0.7879
7
307
Name and Carbon Skeleton
B. P., r.
(a 76()min
*
"3
Additional Data
d-3-Methyl-
cyclopentene-1
(a] D = -f 59.07
4
M 6M = +77.90
o
66.5 to 67 28
% 766mm
0.7663 M
18
1.4222 M
H
C
69 09
@ 765mm
0.772 28
1. 4250 28
69 to 71 41
d?-3-Methyl-
cyclopentene-1
72
0.7851 5S
1.42476"
@ 772mm
0.7705
1.4201 65
66.5 to 67 28
@ 20.0
1.4233"
@ 766mm
0.7715 8l
@16
69 to 71 66
18.9
1.42214"
0.769 28
9,20
n H
@ 16
a
1.43120"
n S
1.43S73"
y
4-Methyl-
cyclopentene-1
P
75 to 76 28
@ 766mm
0.784 28
1.4346 28
c
C-rHu
308
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?.
91"
Additional Data
1-Ethylcyclo-
108
pentene-1
c-c
-123.3"
109 38
0.8000 "
1.4429
1
107 to 110"
0.792 M
@ 21.4
o
106.5 to 107 1B
0.7975 "
0.8041 l5
1.4424
1.4426
@15
1.4402 l6
a
1,4497 16
3-Ethykyclo-
pentene-1
99 to 103
0.7874
1. 43030
@ 758mm
\
c-c
1 ,2-Dimethylcyclo-
0.795,
dD
pentene-1
dt (0to30)
c
-90.4 14
105.03 20
0.78612 M
1.4447 34,38
1 c
-91.3*
105 to 105.2 l4
@30
@ 13.5
rV
103"
0.79501 80
1.4412 M
\J
103 to 103.5 8B
0,7952 M
20
n n
@ 757mm
0.7923
1.44139*
D 20
W 5? a
0.7998 M
1,45115
0.79948 20
1.45142*
15
-8,
0.7992
1.4571 "
0.81283*
1.45717
@
W jff
Y
309
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
n 20
Additional Data
2,3-Dimethylcyclo-
0.780 6
dD - 00009 C
pentene-1
* (0 to 30)
>v .
- 124.8 "
96 to 97 14
0,77155 20
1. 43030 20
<CY
- 118.1 20
95.48 to
@30
"
\ /
95.50 20
0.7831 14
\
0.78055 20
1.432 1 14
c
so
0.78512 20
nlf
@15
1.43972*"
0.79855 20
n",
1.44153 l4
1. 44508 20
20
1. 44724 "
7
3 ,3-Dimethylcyclo-
pentene-1
o
78 to 78.5 3
@ 754mm
0.7580 W
Dl*
1,4190 3
\_J_0
1
c
C,H,
310
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
j>r
fig
Additional Data
1-Propylcyclo-
pentene-1
c-c-c
- 100.3"
13 1.5 to
0.8015 16
1.4450"
132.5 l5
0.8062 M
1.4423
131 to 133 2 <
0.8056
*"
@15
1.4516
1.4574 "
1-Isopropylcyclo-
pentene-1
o-c-c
131.4 to
0.8141
1.45064"
1
133.4
X^s
133 to 135 24
@ 755mm
l-Methyl-2-ethyl-
cyclopentene-1
dt (0 to & 20)
c
1 c-c
127.4 to
127.8
0.8020 17
0.8190 17
1.4490 17
1.4452 17
o
1.4549 17
1.4608 17
W S
311
Name and Carbon Skeleton
M, P.,C.
B. P., C.
@ 760mm
Iff
s
Additional Data
d-l,2,3-TrimethyK
121
0.796 9
[ a jl7.5--_j_19 > 9 M
cyclopentene-1
la].4-28.15* 7
(Laurolene)
122 to 123 70
0.7939
1.4466 70
121 to 122 *
D 26
@18
[Jg- 4-22.8
C
1 C
119 to 120.5 21
120.3 to 121 47
0.7974 21
D 20
1.443 76 M
@ 17.5
[|g-4-23.6 04
\ 7
@ 750mm
0.7991 47
1. 44253 M
[ttj^rs +22.9 70
\
D 20
Wjy .
c
0.79650 21
1.45246"
=*-00008 4 /C
@ 19.5
M ^^ 6
rf/ (5 to 25)
0.7988 70
1.45845"
@ 18.5
M 19 - 6
0.8008
y
@ 17.5
0.8010 21
0.8030 4
@15
0.8048 21
0.8097 21
C,H >4
312
Name and Carbon Skeleton
MP o/" 1
, jr., L.
B. P., C.
@ 760mm
DT
s
Additional Data
M,2,3-Trimethyl-
[)-- 14.5
cyclopentene-1
[ a ]89 ar __15 t 72
(Laurolene)
119 J
118 to 122
0.7871 49
25
1.443 15
25
[a]JJ" 18.13 47
0.7923
1. 44426
0.80187
25
W 1) --29.2 8
18.6
1.4479
0.798
18
~--0.0006 8 /C.
1. 43972
d (15 to 20)
0.8043
wg
15
1.44121 49
1. 44988
1.45099
1.45555 49
s
y
1.45695 49
"S T
1,2,3-Trimethyl-
cyclopentene-1
(Laurolene)
120 to 122
0.7950 o
1.4421 70
(Inactive)
120 to 121"
0.8039
1.4464*
752mm
15
16.5
0.8030
1.4471
15
16.5
U.Jbi
Name and Carbon Skekton
%jr -n or*
M. JTm, U.
B. P., C.
@ 760mm
DT
^
Additional Data
2,3,3-Trimethyi-
v
108.S
0.783 8
1.433
dD t, in
^;_^ _^ fi 0007 / O
cyclopentene-1
* (0 to 25)
(Isolaurolene)
109.2
0.7795
1.4333 *
108 to HO 22
1>5!
1.4324 "
v'V/'
108
0.7830 21
1.43227 21
\ /
108.5
n 20
g-
\
@ 758mm
0.7824 "
1.44136 21
C
108.5 to 109 87
7) 20
w^- 1
@ 754mm
108 to 108.2 21
@ 742mm
0.782 2
0.7812 w-w
0.785 10
1.44690"
Y
109.2
@ 736mrn
108 to 108.2 7i
@ 736mm
16.1
0.7955
15
0.7868 "
0.7867 21
0.7871 "
D 16
0.7949 22
0.7907 2I
O 10
0.7953 21
4
314
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mra
Iff
g
Additional Data
1-Butylcyclopentene-l
o-c-c-c
-95.75"
157.5 to 158
0.8101 15
1.4488 15
6
@ 17.8
0.8123
15
@21.3
1.4461 16
^21.2
1.4554"
n Y
t.4610"
i
Isobutylcyclopentene-*
c
87 to 88 24
0.8203 24
1. 46046"
1
@20mm
w //
c-c-c
1
O
2-Methyl-(2-cyclo-
penten-x-yl)-propane
(/er/-Butylcyclopentene-ff)
139.6
0.7861
1.4417"
C
0.8021 81
c-c-c
1
o
315
C,H,,
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
-8
Additional Data
l-Methyl-3-isopropyl-
cyclopentene-1
c
144 to 146 66
0.801 6fl
1.4478 66
c-c
1
1
c
d-l-Methyl-4-iso-
propylcy clopentene- 1
W D = +66.21
(Apofenene)
143 7
0.7945 e3
1.4403 W
c
1
142 to 143
0.812 '
@21
6
@0
V '
c-c
1
c
3-Methyl-l-isopropyl-
cyclopentene-1
c-c-c
A
138 to 139 6e
136 to 138 8
39 to 41 8
0.791 M
@22
1.4380 66
@22
\ /
C
@ 16mm
316
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
D?
S
Additional Data
l-Methyl-2-propyl-
cyclopentene-x
c
- 130
150.15 to
0.8059
1.4497
1 c-c-c
150.25 >
0.8223
1.4468"
o
@0
9.
\ 1
1.4566"
1.4623 18
7
1,2-Diethyl-
cyclopentene-1
oc
-120 18
148 to 149 l2
0.8136 12
1.4512 i8
1 c-c
@ 761mm
@25
1.4524
(Y
149,20 to
0.8088 18
1.4484"
\-J
149.30 18
0.8124
n a
151 to 152 3 '
D 20
a
@ 751mm
0.8331 18
1.4582 18
0.8252 l
1.4640 J8
3,3-Diethylcyclo-
pentene-1
/s
144 to 146 38
0.8083 38
1. 4469 s8
\J
@ 761mm
Dl Q
1.4455 M - 89
N f-c-c
143.5 to
0.8084 88 - 88
c
144.5 M ' 39
D*
1
@ 754mm
x/o
c
317
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
*s
Additional Data
1 ,3-Dimethyl-2-ethyl-
cyclopentene-1
c
140
0.803 '
1.447 s
' c-c
w// a
\
c
1,2,3,3-Tetramethyl-
cyclopentene-1
*Investigators do not
agree concerning this
structure for cam-
(Campholene*)
133 to 135 88
0.8034 M
1. 44406 M
pholene.
132
0.8035
1.4446"
C
129 to 130.5"
15
1.4445 "
1 C
xSsX
135.5 *
@> 755mm
0.8034
@ 14.5
@ 14.5
> { o
0.8134 3
C
1-Pentylcyclopentene-l
C-(C) 3 -C
178 to 180"
1
o
318
Name and Carbon Skeleton
M. P.,C.
B. P., C.
(} 760m in
*
n D
Additional Data
1 ,1-Dimethylpropyl-
cyclopentene-x
(/cr/-Pentylcyc1opentene-#)
163 to 165 61
0.8256 "
1.4548"
@ 743mm
C
1
1
C-C-C-C
1
o
l-(3-Methylbutyl)-
cyclopentene-1
c
168 to 170 32
0.80 10 32
1.4467"
1
@25
@ 25
c-c-c-c
1
6
3-(3-Methylbutyl)-
cyclopentene-1
86 to 87 9
0.7969
@59mm
22
C-C-C-C
1
c
319
C io
Name and Carbon Skeleton
M. P.,C.
B. P., C.
(M 760mm
X
n ,D
Additional Data
I- 1 ,2-Dimethyl-3-iso-
[]=- 2.0
propylcyclopenterie-1
c
156 to 156.6 52
0.8 II 52
1.447 52
1 c
O/
@ 757.5mm
@ 15
17.6
x
46.2 to 47 62
@ 15mm
\
c-c
1
c
2,3-Dimethyl-4-iso-
propylcyclopentene-1
c
164 to 166"
0.8085 "
1.4503 "
O/
163 to 165 "
22
22
161 to 164"
0.8100"
1.4466"
/ \
c-c c
1
157 to 159
@ 750mm
0.8046 w
1.44591
c
0.8100 "
1.4514"
18.5
18.5
2-Methyl-l ,3-diethyl-
cyclopentene-1*
*Investigator quotes
data from Hoving,
Tabl. Annuelles, II,
c-c
6c
164 *
0.81 1 2
1.450*
151,1911.
"
n a
c-c
320
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
s
Additional Data
1-Hexylcyclopentene-l
C-<C) 4 ~C
204 to 205 72
0.8079
1.4490 72
6
@ 740mm
1,2,3-Triethylcyclo-
pentene-1*
"Investigator quotes
data from Hoving,
Tabl. Annuelles, II,
c-c
181.5*
0.814 J
1.451 2
151,1911.
1 c-c
^^/^
W H
\
c-c
f-2 >3 ,3-Trimethyl-4-iso-
[]=- 6.44 10
propylcyclopentene-1
c
168 to 170 1
0.8095 10
1.4521 1
O/^ c
@19
19
c-c c
1
c
321
C IT HJI
Name and Carbon Skeleton
M. p.,c.
B. P., Q C.
@ 760mm
z>:
ng
Additional Data
3-Dodecylcyclo-
pentene-1
o
172
@ 15mm
0.8262
@18
1. 45667 s
\
C-(C)io-C
322
(1) O. Aschan, Ann. 200, 185, 1896.
(2) K. v. Auwers, Ann. 415, 98, 1918.
(3) A. Bhal, Bull. soc. chim, [3J 13, 841, 1895.
(4) G. Blanc, Ann. chim. [7] 18, 181, 1899.
(5) G. Blanc, Bull. soc. chim. [3] 19, 699, 1898.
(6) G. Blanc, Compt. rend. 145, 681, 1907.
(7) L. Bouveault and F. Levallois, Compt. rend. 146, 180, 19O8.
(8) L. Bouveault and L. Tetry, Bull. soc. chim. [3J 27, 307, 1902.
(9) J. v. Braun, E. Kamp, and J. Kopp, Ber. 70, 1750, 1937.
(10) J. v. Braun and P. Kurtz, Ber. 67, 225, 1934.
(11) E. P. Carr and H. Stucklen, J. Chem. Phys. 6, 55, 1938.
(12) F. H. Case and E. E. Reid, J. Am. Chem. Soc. 50, 3062, 1928.
(13) G. Chavanne, Bull soc. chim. Belg. 31, 331, 1922.
(14) G. Chavanne, Bull. soc. chim. Belg. 39, 402, 1930.
(15) G. Chavanne and P. Becker, Bull. soc. chim. Belg. 36, 591, 1927.
(16) G. Chavanne and L. De Vogel, Bull. soc. chim. Belg. 37, 141, 1928.
(17) G. Chiurdoglu, Bull. sci. acad. roy. Belg. 17, 1404, 1931.
(IS) G. Chiurdoglu, Bull. soc. chim. Belg. 42, 347, 1933.
(19) G. Chiurdoglu, Bull. soc. chim, Belg. 43, 35, 1934.
(20) G. Chiurdoglu, Bull. soc. chim. Belg. 47, 363, 1938.
(21) A. W. Crossley and N. Renouf, J. Chem. Soc. 89, 26, 1906.
(22) A. Damsky, Ber. 20, 2959, 1887.
(23) M. Dojarenko, J, Russ. Phys. Chem. Soc. 58, 27, 1926.
(24) F. Eisenlohr, Fortschr. Chem. Physik. 18, No. 9, 1, 1925.
(25) C. Gartner, Ann. 275, 331, 1893.
(26) M. Godchot, Bull. soc. chim. [5] 1, 1153, 1934.
(27) M. Godchot and G. Cauquil, Compt. rend. 191, 1326, 1930.
(28) M. Godchot, M. Mousseron, and R. Richaud, Compt. rend. 200, 1599, 1935.
(29) M. Godchot and F. Taboury, Compt. rend. 156, 470, 1913.
(30) M. Guerbert, Ann. chim. [7] 4, 289, 1895.
(31) C. Harries and L. Tank, Ber. 41, 1701, 1908.
(32) J. McA. Harries, J. Am. Chem. Soc. 51, 2591, 1929.
(33) W. Huckel, K. Kumetat, and H. Severin, Ann. 518, 184, 1935.
(34) N. Kishner, J. Russ. Phys. Chem. Soc. 37, 513, 19O5.
(35) N. Kishner, J. Russ. Phys. Chem. Soc. 40, 676, 1908.
(36) N. Kishner, J. Russ. Phys. Chem. Soc. 4O, 994, 1908.
(37) N. Kishner, J. Russ. Phys. Chem. Soc. 42, 1211, 1910.
(38) N. Kishner, J. Russ. Phys. Chem. Soc. 43, 1149, 1911.
(39) N. Kishner and P. Amosow, J. Russ. Phys. Chem. Soc. 45, 957, 1913.
(40) W. Koenigs and C. Meyer, Ber. 27, 3465, 1894.
(41) W. Markownikow, Ann. 307, 335, 1899.
(42) W. Markownikow, J. Russ. Phys. Chem. Soc. 31, 214, 1899.
(43) H. Meerwein and H. Probst, Ann. 405, 142, 1914.
(44) W. Meiser, Ber. 32, 2049, 1899.
(45) J. Meyerfeld, Chem. Z. 36, 549, 1912.
(46) W. A. Noyes and C. G. Derick, J. Am. Chem. Soc. 31, 669, 1909.
(47) W. A. Noyes and C. G. Derick, J. Am. Chem. Soc. 32, 1061, 1910.
(48) W. A. Noyes and L. P. Kyriakides, J. Am. Chem. Soc. 32, 1064, 1910.
(49) W. A. Noyes and G. S. Skinner, J. Am. Chem. Soc. 39, 2692, 1917.
(50) O. Philipow, J. Russ. Phys. Chem. Soc. 46, 1141, 1914.
(51) H. Pines and V. N. Ipatieff, Unpublished data.
(52) F. Richter, W. Wolff, and W. Presting, Ber. 64, 871, 1931.
(53) I. J. Rinkes, Rec. trav. chim. 57, 176, 1938.
323
(54) M. van Rysselberge, Bull. soc. chim. Belg. 35, 311, 1926.
(55) F. W. Semmler, Ber. 26, 774, 1893.
(56) F. W. Scmmlcr, Ber. 37, 234, 1904.
(57) W. Thiel, Ber. 26, 922, 1893.
(58) F. Tiemann, Ber. 30, 594, 1897.
(59) F. Tiemann, Ber. 33, 2935, 1900.
(60) L. Tschugaev, Ber. 37, 1481, 1904.
(61) A, I. Vogel, J. Chem. Soc. 1938, 1323.
(62) J. Walker and J. Henderson, J. Chem. Soc. 69, 748, 1896.
(63) O. Wallach, Ann. 369, 83, 1909.
(64) O. Wallach, Ann. 408, 163, 1915.
(65) O. Wallach, Ann. 414, 195, 1918.
(66) O. Wallach, Collmann, and Thede, Ann. 327, 131, 1903.
(67) O. Wallach and K. v. Martius, Ann. 365, 272, 1909.
(68) J. Wislicenus and C. Gartner, Ann. 275, 331, 1893.
(69) N. D. Zelinsky, Ber. 35, 2488, 1902.
(70) N. D. Zelinsky and N. Lepeschkin, Ann. 319, 303, 1901.
(71) N. D. Zelinsky and N. Lepeschkin, J. Russ. Phys. Chem. Soc. 33, 554, 1901.
(72) N. D. Zelinsky, S. E. Michlina, and M. S. Eventowa, Ber. 66, 1422, 1933.
324
Name and Carbon Skeleton
M. P. t C.
B. P., C.
760mm
Pf
-8
Additional Data
Cyclohexene
83
0.8098
1.4465
^~ -0.000940,
-80"
83 10T
@ 777mm
83.5 24
0.7355
0.7713 1W
1.4428 lw
27
1.4437 "
(1 -0.0003150 /C.
(10 to 100)
@ 765mm
61.8
25
** (10 to 30)
82.3 80
0.7720 lw
1.4445 M
764mm
84"
0.7731 1W
25
1.44507
Reference " gives n L i
@ 763mm
59.8
22.1
and Wyj.
83 to 84
0.7823
1.445 12
@ 762mm
50
21
83 to 84 "
0.7890 107
1.4463 7 l27
@ 761mm
@41.9
20.05
84 to 86 1M
0.7896 1OT
1.4459 13S
83.5 130 - 136
41.2
1.4460 130
83.3 "
0.8054 18
1. 44646 l07
83.1 2<J
@27
1.4465 l6
83 to 83.5 3
0.8034
1.4469 26 - 69
@25
83 to 84 12 ' 4 ". 82
0.8064 l07
1. 44577"
82. 7 l6
22.7
18.7
82 to 84 9 -
0.8081 "
1. 44902 18
@1 /C A O
81. 5 to
6&22 1
16.4
82.5
0.809 12
1.44921"
/75> 1 C 1
81 to 82 28
21
v$ 15.1
80 to 81
0.8021 "
1.4494 81
13.5
82.8 l "
759mm
0.805 10>
0.8088 10T
1.44235 u
81 .5 to 82. 5"
0.8098 18
a
756mm
1.44360 m
0.810 2
83 to 84 "
^a
@ 753mm
0.8101
1.443*69 1OT
83 to 84 M
0.8102 "
w ?o
@ 752mm
0.8104 a
1.443*02
0.8112 w
0.7995 74
^a
1.44516 *
Z?20
n S* 4
0.809
rjto
1.44610
1.44623
njj.
1.44653
325
Name and Carbon Skeleton
M. P.,C
. P., c.
@ 760mm
D?
1.5
Additional Data
Cyclohexene*
Continued)
0.81 13 7
1. 43998 M
@ 18.7
wg-*
0.8120 24
@ 18.4
1.45184"
0.8111 w
"0
@ 17.4
1.45312 l87
0.8138 26 - 31
n M
@16.5
1. 45326 lw
0.8143 3 . 107
W 3
@ 15.6
0.8147 8
1.45252"
0.81 56
1. 45475
@ 14.9
W S' 4
1. 79934 74
@ 14.4
1. 45573 s58
0.8183 3 '
1.45596"
0.80893 M
H P
/>!
1.45620 s
1.44943 7<
1.45743 "
Y
1. 45874 m
5*
1. 45854 1W
w 20
X
1.45827 "
n !8.7
7
1. 46039 M
r
1.46133 M
n 1 *-*
1.46194*
*2; 1
1.45507 M
nj^
326
Name and Carbon Skeleton
Kjf O Q f
M. Jr., C-.
B. P., C.
@ 760mm
iff
-B
Additional Data
1-Methylcyclohexene-l
109.S
0.811 7
1.450
^=-0.0009,/C.
* (15 to 65)
c
109.1 to
0.7734
1.44234 *
1
109.3 a
@62.1
1.4496 ll2
@ 772mm
0.7743 iro
1.4497 2 -
110.5 to
@6l.l
1.4498 M
111.5 29
@ 770mm
109.5 to
0.7912 l07
@42.1
0.7918 IOT
1.4503 72
1.45067 l07
110.5 78
@ 770mm
@41.4 C
0.799 111
1.4503*
@ 18.5
110 107
0.8066 4!>
1.44094"
@, 769mm
@ 18
108.0 to
0.8099 130 133
1. 45042
108.5 22
0.810 6
@17.9
@ 769mm
0.8103 2
1.4499 1
109 62
0.8106 22 - 1OT
@ y !7.5
@ 768mm
0.840 112
1.4508
109.6 to
0.81 18 44
@ 17.5
110.2 79
0.8122 "
1.4543 31 - 33
@ 767mm
0.8127 107
@ 13.5
103.5 2
0.8022 M
1.458
@ 767rnrn
@ 12
111 to
i^20
1. 44766 107
112 2'- 2
0.809 8
w ?/
110.6 31
110.5 to
1^20
0.80305 2
1.44 744 2
r%20
HI 130,133
HOto 112 3t)
0.7999 2
1.44 763 7B
71 20
110 to
a
110.5 10
0.8005 e2
1.45745 l07
110
D?
W ^/s
109 to HO 98
0.81 IS 2
1.45711 2
108 82 ' 83 ' 84
18.5
w- 6
106 to 107 "
0.81 IS 79
ft
1. 45735 w
103 to
(Q), lo.2
n 17 * 9
105 2 - 85
0.8075 46
H ft
107.5 to
Pi?
1.46259 1W
108.5
n Hy
@ 759.5mm
1.46293 s
108.9 to
ng- 6
109.2 2
T
@ 754mm
1. 46328
327
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
s
Additional Data
1-Methylcyclohexene-l
(Continued)
109 to 110 72
0.8117"
@ 753mm
17.9
106 to 107
0.8145 2
@ 751. 5mm
@ 14.8
108 3
0.8182 lw
@ 747mm
14.2
0.8257 31 - 33
n 13.5
-^13.5
0.8166 2
0.8172 2
D
0.821
0.823 82
Dl
0.827 83 - 84
3-Methylcyclohexene-l
104.4
105 to 106 50
0.7950 30
1.4408 ao
105 a2
@26
@26
\
c
104 to
106 95
0.80177 63
rj21.8
1.44236"
! .4445 c, 109
104 to 105 3
0.8048 60
1.4454 50
104,i3o
@ 20.3
1.445 1 130
103 to
0.805
@ 17
105 ' 82 - 109
0.806 1W
1.4459 3S
103.25 to
0.8009 13
@ 14
103.5 M
@ 752mm
0.803 35
104 35
@ 743mm
328
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
iff
g
Additional Data
4-Methylcyclohexene-l
102.5 to
0.8000 13
1.4419 70
102.7 70
0.8001 70
1.4423"*
I
@ 772mm
0.8003 M - w
18
i
c
103 to 106 < 7
p20
1.442
@ 765mm
0.7986 60 - 61
@17
104 to 105 12
D 20
1.4445 35
@ 762mm
/y
@14
102 to 103 37
0.8023 24
* *
! .4449 si .32
102.5 to
($ l/.o
@ 13.5
103.5 *
0.804 12
@17
1. 44138
102.5 to
103 13
0.8047 w - 61
w2
D 16
1. 45069 M
102.8 to
X/16
W 17.8
103 10
0.805 36
103 61
@14
1. 45620 M
105 67 - 82
0.8086 31 - 33
W S* 6
r^lS.5
102 to 102.5 8B
^ia.a
@ 755mm
0.819 M
101 to 102"
D
@ 754mm
0.8207 w -
101. 9 - 81
@ 753mm
102.5 2
@ 750mm
102.5"
@ 743mm
d-4-Methyl-
cyclohexene-1
[]J+ 107.05
102 l28
0.8002 128
1.4443 128
@ 757mm
@16
@16
101.9"
@ 753mm
329
C,H,,
Name and Carbon Skeleton
Jlf. P.,C.
B. P., C
760mm
Iff
ng
Additional Data
3- or 4-MethyJ-
WD- + 17.78
cyclohexene-1
[a^- +81.47
r^i r^i
106 to 107 ll8
0.7937 l29
1.4387 129
[ ) or f J
103 to
@27
@27
X NX"\ \S
^ t
103.5 "
0.799 116
1.44234 ll
c 1
c
@ 750mm
0.8019 18fl
t .4444m
105 to 106 m
@ 745mm
C 8 H 14
1-Ethylcyclohexene-l
c-c
135 to 136 2
0.8171 49
1.4547 48
1
@ 768mm
0.8217 a2
@ 22.3
135.8 to
0.8260 63 - 124
1.4583 98
136.8 "
0.828 M
1.4576 M - 124
@ 768mm
1.4567 32
135.7 to
136.6 w
0.8238 *
@ 191
@ 19.05
1.4591 1S4
134 to 136 124
0.8235 l24
@19
134 to 134.5 22
1.45966"
134tol35 124
0.8268 7fl
@ 15.25
134 M - 84
@ 15.5
1.45386 2
134 to 135
0.8270"
M ^06
@ 75 1.5mm
15.25
1.45694"
4911
M 16.26
Jf
@30mm
a
1.46347 2
1.46673"
1.46944 2
t
1.47269
tf
330
Name and Carbon Skeleton
M. P.,C,
B. P., C.
@ 760mm
D?
<
Additional Data
1,2-Dimethyl-
136
0.823 2
dD_ oooog/ o c
cyclohexene-1
rf/ (15 to 30)
c
136 to
0.81495 17
1.4580 131
1 c
137.5 84
@30
@ 21 5
a
135.5 to
137.7 17
0.8226 131
0.82317 17
1.460 4
1.4590 98
135.5 to
0.8234
1.4587 1 "
136.5 131
0.824 4 ' 1 "
1. 45664
135.4 to
135.9
0.826 98
1.462 82
Dll
@ 14
135 to
137 65 - n <
0^8269 l31
1.46178 8
15
@ 13.5
1 ?7 82,86
I > '
0.82726 l7
1. 45643 17
15
W 5* a
830 82
1. 45906 3
14
w g.6
0.8315 3
@13.7
1. 46663 17
n 20
0.8317 3
^fl
@13.5
1. 46908 3
0.841 1 82 - 86
wj;- 6
Dl
1. 47244 17
-s,
1.47517 3
w^
1 ,3-Dimethylcyqlo-
hexene-1
0.802 6
~--0.00082/C.
d/ (15 to 30)
c
128.0 to
0.79448 17
1.4487 <J
1
128.4 17
1.44501 17
124 to 126 80
0.8006 80
n 'u
\
0.8026 17
1.45462 17
c
0.80677 17
(a 15
*
jl. 46013 1T
331
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
D?
nJJ
Additional Data
1 ,4-Dimethylcy clo-
127.5
0.801 6
1.445 U
^--00009,'C
hexene-1
rfi (0 to 30")
c
-59.4 17
127 to 129
0.79240 17
1.44372 3
764mm
30
22
128.7 "
0.7985 8
f..
128.5 131 - 13S
22.4
1.4457] 132 -
1
127 to 128 114
0.7989 *
l
c
125.6 to 126 33
22
1.4459 '"
125 82,8tt,87
f.
1.4461 71
127.5 to 128 71
0.8005 > 32 -
1.4502 49
@ 756mm
1 136
19
124 to 126 3
0.80061 17
1.451 82 - 87
75 1mm
0.8024 71
14
0.8030 49
1.4486 31
0.8020 lu
13.5
19.5
1.44112 3
0.80472 > 7
W 22.0
15
1. 44300 17
0.8111 82 ' 87
w 20
14
a
0.8175 3l > 33
1. 45056
13 5
w .,
^13.5
/*
0.8207 2 - 7
1.45242"
W S
0.8208
1. 45626 3
^0
7
1. 45805 l7
7
C$HU
332
Name and Carbon Skeleton
M p r
1VJL. f .) \s.
B. P., C.
@ 760mm
Iff
B
Additional Data
1 ,5-Dimethylcyclo-
127
hexene-1
c
127.5 to
0.7998 8
1.44533 8
128.5
@22.6 9
@ 22.4
127.4 to
0.8000'
1.4466 138
127.8 8
@22.4
@22
c
124 to
0.8015 1M
1.4466" 4
126
@22
@21
124 to 125 80
0.8025 "<
1.4430 W
124 M - M
@21
1.4480"- w
127 to 129"
0.8056
1.451'
@ 758mm
0.807
1.4547"
126 to 127 "
0.805 w
@ 19.5
@ 750mm
>S
1.451 M
0.8005 60
@ 12
18
1.44263
0.8122
fta
12
1.45215
0.8210 82 ' M
W S' 4
1.45795*
i
3 ,3-Dimethylcy clo-
hexene-1
r^^i r^^
118.5 to
0.7970
t.4439
L ]/ or 1 1
120
@21
@21
^^^N ^S/^
@ 752mm
C /\
C C
333
C,H,,
Name and Carbon Skeleton
M. F.,C
B. P., C.
@ 760mm
*
s
Additional Data
3 ,5-Dimethylcyclo-
hexene-1
125 to 126 T
0.797 8
1.44361
c c
@ 764mm
124 to 126
124 to 125*
0.8065 7
@ 20.6
2U
1.45083*
(^20.6
126 to 127*
@ 746mm
0.8062 '
@ 19.4
1.44933 '
20.2
0.8074 7
1.443*
@ 18.4
@18
0.8101
1.45372 '
@1 R
0.8005 "
1
1.45082*
0.8009
1.44603
@15.6
@ 15.6
1. 44086 8
a
1.44784
n*
1.44634'
1.44793
w^
1. 45014 *
1.44315
1.45020*
H fi
1.45801 '
1.45642 7
1.46078*
**;
1.45800*
1.45263 *
334
Name and Carbon Skeleton
K/t T> o/* 1
M. jr. t L.
B. P., C.
@ 760mm
' iff
8
Additional Data
3 ,5-Dimethylcyclo-
hexene-1
(Continued)
1.45587'
1.46413 7
y
1.46255'
20.2
H H
1
1. 46728'
H 18.0
n u
1
1.46390'
y
1.45835 s
H'*
y
4,4-Dimethyl-
cyclohexene-1
117 to 117.5 *
0.7970 20
1.443S 1
@ 770mm
D%
1.4479"
/\
c c
119.5 to
121.2
0.803 *
0.8092
@ 16.6
1.44521 6
@ 767mm
@ 16.6
@ 16.2
120 to 122 < 3
0.8056 6
1.4425 1 5
120 to 122 6
@ 16.2
wj-*
@ 750mm
0.80267 20
1. 44218 M
0.8040 20
1. 44604
PIS
M- 5
0.8089 '
1.45182 6
@13.5
M l 2
0,81 29
1.45137 M
1.45531
ng^
1.45722*
y
1.45700"
i/- 8
y
1. 46100 c
w //* 6
y
335
Name and Carbon Skeleton
M. P.,C.
B. P. t C C.
@ 760mm
D?
8
Additional Data
1 -Propylcyclohexene- 1
c-c-c
154.7 to
0.826 "
1.4578 88
157.7 8
7) 20
1.4541 w
154.5 to
0.838 12
@19
155.5 97 - 120
@19
1.4579 '20
15483,84
0.8181 7
(i 19
19
1-Isopropylcyclo-
hexene-1
c-c-c
156.5 2
0.826 2 - s >
1. 4594 s8
@ 772mm
0.829 123
1.4593 2 - 6
156 2 -
0.830 fl8
1.4606 123
155 to 157 l23
D 20
1.46150 2
151. 7 to
0.8302 2
15.2
154.5 98
@ 15.2
1. 45884 s
161 to 162 22
0.8320 2
HJ-
@ 755mm
12.9
1.46851 2
87 to 88 22
i j 1 f> ,2
@20mm
H 3
1. 47436 2
"y
3-Propylcyclohexene-l
r*\
155 to 156 "
0.8240
1.4564
U\
C-C-C
336
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Df
$
Additional. Data
l-Methyi-2-ethyl-
cyclohexene-1
c
156.7 to
0.832 w
1.4630 M
1 c-c
157.0 M
DS
3-Methyl-l-ethyl-
cyclohexene-1
or
5-Methyl-l-ethyl-
cyclohexene-1
149 to 151 M
0.813
1.4537
c-c
148 to 149
0.8296 M
i.454 66
0.8366 M
\
c
or
C-C
r'S
/u
c
d-3-Methyl-l-ethyl-
[a] D = +56.r*
cyclohexene-1
or
c/-5-Methyl-l-ethyl-
cyclohexene-1
148 to
0.8087 1W
1.45 14
149 1M
@25
2S*
@ 743mm
337
Name and Carbon Skeleton
M. P.,C.
B. P., C.
< 760mm
Of
wg
Additional Data
4-Methyl-l-ethyl-
cyclohexene-1
0.814 6
1.452 6
~-0.00066/C.
(0 to 20)
c-c
153 to 154 u
0.8145
1.4514 "
A
151.5 to
@22
@22
\\
151.7 98
0.8133 7l
1.4510"
v
151 to 152 71
0.814
1.4522"
1
c
149 8,82,87
0.814 98
D 20
1.4528 98
1.453 2 ' 87
0.8169 82 87
16
@16
0.8278 82 ' 87
@0
4-Methyl-2-ethyl-
cyclohexene-1
c-c
15 1.9 to
0.815 98
1.4544"
fY
152.1 88
D 20
1
c
1,2,3-Trimethyl-
cyclohexene-1
c
149.6 to 150 4
0.828 4
1.4593*
6:
c
749mm
0.8347 4
@ 11.75
1. 46296 4
11.75
1.46015 4
a
1.47021 4
w"- 76
1.47603 *
n ll.T
T
00 HI<
338
Name and Carbon Skeleton
M. JVC.
B. P., C.
@ 760mm
Iff
s
Additional Data
1,2,4-Trimethyl-
cyclohexene-1 or -5
c c
0.8184"."
1.4561 3l .
7 c | c
r'V fCY
DM
@ 13.5
U U
I 1
c c
1,3,5-Trimethyl-
cyclohexene-1
c
1
139 to 141 >
@ 766mm
0.7941
@ 24.7
1.44378 3
@24.7
O 1
142.5 to
0.7965
1.447 12B
143.5 l26
@21
21
c c
140.5 to 142 8
140 3
0.8025
@ 14.3
1. 44909
@ 13.5
0.8048
1. 44917 3
@ 13.8
@i3.r
0.8031 3
1.44102 8
1.44604*
1.44625 3
1.45057 s
1.45591 '
w w"
1. 45596 s
1.45638
n^
1.46155 a
*H*
1.46154*
nl H*
339
Name and Carbon Skeleton
TUT p r
1VL , JT . 9 U
B. P., C.
@ 760mm
D?
s
Additional Data
1,4,4-Trimethyl- .
cyclohexene-1
c
139.5 to
0.8021 *
1.44422 6
140.5 B
@23.15
^23.15
44.4 6
0.804 *
1.4456 s
@21mm
0.8032 6
1.44592*
/\
36.3 to 37.3 *
@ 18.8
@ 18,9
c c
@ 14mm
0.8096 *
1.44921 *
0.8098 *
1.44152*
14.8
wg- 1 *
a
1.44322*
A
1.44643*
a
1.45086*
1.45263*
1.45591*
w ;
L45652*
i
1.45822
7
1.46164
n a' 1
y
340
Name and Carbon Skeleton
H.P..-C.
fi. P., C.
@ 760mm
or
w 20
Additional Data
ciJ-l,4,5-Trimethyl-
cyclohexene-1
c
14709
0.814"
1.44905"
1
c |
c
tran$-l ,4,5-Trimethyl-
cydohexene-l
145"
0.805 "
1.44820"
1,4,5-Trimethyl-
cyclohexene-1
(Mixtures of cis and
trans isomers)
144 to 146
0.805
0.8078 >
1.4482 1
1.44990 >
& 16.25
@ 16.25
1.44742 l
-jlJ.25
1.45683 '
1.46264
341
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
DT
8
Additional Data
2,3,3-Trimethyl-
cyclohexene-1
c
146.2 to
0.8217 6
1.45603 8
a c
147.2 *
@ 20.3
@ 20.4
@ 767mm
0.8278 B
1. 45859 s
144 to 146
@ 15,0
@ 14.8
c
0.8300
1. 458S9 6
@15.0
@ 15.0
0.862 2
1.4590"
1. 45336 6
^20.4
1. 45638
n U.Q
1.45602*
n%*
1.46298 8
1.46597 6
1.46567*
1.46877 6
1.47173*
15.0
H H
1
1.47183*
V
342
Name and Carbon Skeleton
M p r
M . -* J V't
B. P., *C.
@ 760mm
D?
ft 20
Additional Data
2,4,4-Trimethyl-
cyclohexene-1
c
138 to 139
0.7981 M
1.4453'
tf
C C
137 to 140 w
139 to 141 60
@ 759mm
138 to 142 '
@ 735mm
0.791 1 38
@21.5
0.8094
@ 17.8
0.8085 19
1.44612 38
1.44671
1.4473
@ 14.4
0.8117 fl
14.4
1.44402"
w //' 8
1.45332
1.45900 e
H H A
3,5,5-Trimethyl-
cyclohexene-1
c j^J
138 to 140 101
0.7978 101
1.4434 101
c c
1-Butylcyclohexene-l
c-c-oc
6
180.8 to
182.9 M
0.828 M
D 20
1.4591 M
343
Name and Carbon Skeleton
M. P.,C
B. P., c,
760mm
iff
-8
Additional Data
M-$ec-Butylcyclo-
Wg 4.06-
hexene-1
c
i
172 to 174 64
0.8410
1.4590 64
1
c-c-c
172tol74.5 2
0.829 "
1
@ 755mm
n 20
1^20
4-terButyl-
dD
cyclohexene-1
dt (20 to 40)
172
0.81 73 78
1.4587 7
@ 745mm
@40
0.831 5 7fl
1
c-c-c
1
c
l-Methyl-2-propyl-
cyclohexene-1
c
177.3 to
0.832 "
1.4627 98
I c-c-c
177.8 98
n 20
a
C 10 Mil
344
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
-s
Additional Data
1- or 3-Methyl-2-
isopropylcyclohexene-1
c c
165 to
c 1 1
| c-c c-c
168 ' l <
a- a
c
l-Methyl-3-isopropyl-
cyclohexene-1
c
1
164 to 168 "
1.4561 119
0,
c-c
1
1
c
l-Methyl-4-isopropyl-
cyclohexene-1
c
174 to 175 U3
0.821 113
1.4551 113
o
21
c-c~c
345
C io
Name and Carbon Skeleton
tf TJ O/" 1
M. Jr. t C,
B. P., C.
@ 760mm
iff
5
Additional Data
d-l-Methyl-4-isq-
propylcyclohexene-1
175tol77 lws
0.8258 *
1.4580
174 to 176 8
0.829 92
1.460 1 92
173 to 174 w
0.8246 10fl
1.4563 106
171 to 172 92
M-Methyl-4-iso-
propylcyclohexene-1
[a] /) --2.07w
172 to 174.5 62
0.8230 62
1. 45979 51
@ 16.5
l-Methyl-2-propyl-
cyclohexene-x
c
| c-c-c
a
167 to 1 70 8
0.848 68
0.8611
1.469 M
2-Methyl-4-isopropyl-
cyclohexene-1
c
169 to 172 9I
0.828 ttl
1.462 "
O/
167 to 168 42
0.8222 42
@0
D 20
1,45683 42
I
c-c-c
C io Hit
346
Name and Carbon Skeleton
TUT P *c
jyj., jT t t".
B. P. t C.
@ 760mm
Iff
*8
Additional Data
3-M^thyl-l-propyl-
cyclohexene-1
or
4-Methyl-2-propyl-
cyclohexene-1
c-c-c
168 to 171"
0.8302 M
1.456 M
@15
0.8375 M
\
@0
c
, , or
c-c-c
'a
1
c
3-MethyH-isopropyl-
[a]^=-f 23.34 * 4
cyclohexene-1
or
4-Methyl-2-isopropyl-
cyclohexene-1
d-form
168 to 169 78
0.8125 *
1.4519 84
764mm
@25
@25
C
165 "
6C-C
v-C^
c 1
c
dl-lorm
165 34
0.8154 '*
1.4534 '*
*
25
25
347
Name and Carbon Skeleton
TUT P r*
4KZ. JT.) U.
B. P., C.
760mm
DT
Additional Data
3-Methyl-6-isopropyl-
cyclohexene-1
c
167.1
0.824 M
1.461 M
1
c-c
@ 768.6mm
55 to 56 w
C j
@ 12mm
c
4-Methyl-l-propyl-
cyclohexene-1
c-c-c
173.2 to
0.815
1.4533 M
1
174.2 w
n 20
^20
173 to
17(5117,118
1
c
4-M ethyl- 1 -isopropyl-
cyclohexene-1
c-c-c
175"
0.823
A
170 88
Dl
fi
166 to 167
0.827
^
z)S
1
c
348
Name and Carbon Skeleton
M. P.,C.
B. P., *C.
@ 760mm
D?
-
Additional Data
d-4-Methyl-l-iso-
Mg- + 115.64 "
propylcyclohexene-1
(aj^s-f-112.75 128
168 to
0.7632 M
1.4532 128
168.5 '
@, 79.8
@16
[aJ2- 6 *-f 32.77 1W
@ 758mm
0.81 18 1M
1. 42042 24
165.5 "*
0.8132 105
n ff*
@ 739mm
0.8132 2 <
a
1. 44970
@ 16.8
n 1 **
0.8141 128
@ 16
a
1. 42920 8 <
1. 45906 w
1.43432 24
79.b
7/ 7
1. 46460 2 <
V
l-Methyl-4-propyl-
cyclohexene-x
c
i
168tol70 82 - 7
0.8270 2 - 87
1.455 82 - 87
X
16
@ 16
o
0.8387 82 - 8 '
i
c-c-c
349
Name ami Carbon Skeleton
Af. P. t C.
B. P., C.
@ 76()nim
Iff
L
Additional Data
4-Methyl-2-propyl-
cyclohexene-1
c-o-c
ry
172.6 to
173.29 8
0.816 98
n 20
/'au
1.4546 08
XX
- \
c
5-Methyl-3-propyl-
cyclohexene-1
or
3-Methyl-5-propyl-
cyclohexene-1
o
169 to 170 60
0.8197 60
16
1. 45609 60
@16
AA
c c-c-c
or
c-c-c c
1,2-Diethylcyclo-
hexene-1
c-c
54 to 55
1 c-c
@ 10mm
C 16 Ml f
350
Name and Carbon Skeleton
MZ> /*
, f. t V.
B. P., C.
@ 760mm
X
s
Additional Data
3,5-Diethylcyclo-
hexene-1
163 to 166 41
0.83141 4I
n 20
'^20
1.46519"
c-c c-c
4,4-Dimethyl-2-ethyl-
cyclohexene-1
c-c
&
69 32mm
0.832
1.4616
X
C C
l^^S-Tetramethyl-
cyclohexene-1
c
169 M
0.828
1.46053 "
c
l^4,5-Tetramethyl-
cyclohexene-1
166 M
0.817 w
1.45722 w
351
Name and Carbon Skeleton
\t p 0/"i
JaU. A., C-.
B. P., C,
@ 760mm
D?
-B
Additional Data
1 ,2,4,5-Tetramethyl-
cyclohexene-1
165 to 167
0.817*
1.4572 i
0.8199
1. 45880 >
@16.5
16.5
1.4561 7 >
1. 46597 l
JJ'*
1.47192
2,3,4,4-Tetramethyl-
cyclohexene-1
c
169 to 172 91 - 94
0.828 91 - 94
1.462"'"
Q/
167 to 169"
0.8208 "
1.4621 &8
62. 5 to 65 68
#2!
1.4629"
c
@ 17mm
0.8328 80
(m 15
c c
/?;;
CllH.20
1-Pentylcyclohexene-l
C-(C)i-C
203.4 to
0.83 1"
1.4605"
1
205 "
n 20
O
Ctf
352
Natne and Carbon Skeleton
MP C
, i .f i./.
B. P., *C.
(& 760mm
D?
1,5
Additional Data
2-Cyclohexen-l-yl-
pentane
oc-c-c-c
19483,84
0.856 8 <
3-Methyl-l-cyclo-
hexen-1-yl-butane
c
1
oc-c-c
6
194.5 to
196.5
0.826
n 20
1.4596"
l-Methyl-2-butylcyclo-
hexene-1
c
| OC-C-O
o"
197.8 to
199. 1"
0.833
n 20
^20
1.4637 M
4-Methyl-l-butylcyclo-
hexene-1
c-c-c-c
6
196.3 to
197.1
0.818"
DJS
t.4558*
1
C
353
Name and Carbon Skeleton
M. P.,C
B. P., C.
< 760mm
/
*s
Additional Data
4-Methyl-2-butyl-
cyclohexene-1 "
c-c-c-c
195.2 to
0.820 8
1.4574 98
a
195.7 8
\
c
4-Methyl-2-(2-methyl-
propyl)-cyclohexene-l
c
184.1 to
0.8 1 2 8
1.4530 98
1
186.2 M
r> 20
c-c-c
r"Y
y
c
l,S-Dimethyl-2-iso-
propylcyclohexene-1
? c
180 to 183"
0.8550 "
1.4585 "
1 |
@ 763mm
25
@25
1 j~~ c ~ c
184 to 186"
1.4600"
}^s
@ 767mm
@25
c
68 to 74 "
1.4578 "
@ 10mm
17
354
Name and Carbon Skeleton
M. P,,C.
B. P M C
@ 760mm
Iff
B
Additional Data
l,5-Dimethyl-2-iso-
propylcyclohexene-1
or -6
c
185 to 187
0.8215 "
1.4579
c 1
6C-C
@ 764mm
@23
@23
/
186 to 187
0.8432
.
Do
c
or
c
c 1
| c-c
^v
D
c
l-Methyl-2-pentyl-
cyclohexene-1
c
218.9 to
0.834 *
1.4646 98
| C-(C)a-C
a
219.793
DM
355
Name and Carbon Skeleton
Af. P.,C.
5. P., C.
@ 760mm
Iff
"8
Additional Data
4-Methyl-2-(3-methyl-
butyl)-cyclohexene-l
or
3-Methyl-l-(3-methyl-
butyl)-cyclohexene-l
c-c-c-c
209 to 211 6
0.8190 M
0.8301 M
1.459 M
1
c
or
c-c-c-c
1 1
o:
c
4-Methyl-l-(3-
methylbutyl)-cyclo-
hexene-1
c-c-c-c
1 \
21Q82.87
0.8213 M ' 87
16
1.458 M - 87
0.8333 .w
@0
c
4-Methyl-2-ethyl-l-
isopropylcyclohexene-1
[]J}-+ 39.18"
c-c-c
I c-c
90 to 92 n
21mm
0.8302 "
@25
1.4614"
25
II
73 to 75 "
1.4610"
. 1
@ 10mm
@25
I
c
356
Name and Carbon Skeleton
M. P.,C.
B. P., C.
(?) 760mm
a
s
Additional Data
l,2,4-Trimethyl-4-iso-
propylcyclohexene-1
c
93 to 95 78
0.84231 78
1 .46635 78
rV
(^ 20mm
0.860 78
@25
1.46363 78
kj
wg
X
c c-c
1
1.4729978
1
c
1,478S6 7
4-Methyl-2-propyl-l -
isopropylcyclohexene-1
[] = +35.90"
c-oc
100 to 103"
0.8348 "
1.4605"
1 c-c-c
@ 18mm
@25
@25
c
357
C/ 14 1*1
Name and Carbon Skeleton
Af. P.,C.
B. P., C.
@ 760mm
D?
ng
Additional Data
4-(l,l,3,3-Tetramethyl<-
butyl)-cyclohexene-l
c c
113 73
0.8565 73
1.4741 7a
(I Vc-c-c-c
\ / i i
@ 12mm
25
@25
V ../ l I
C
1 ,3 ,3,5,5-Pentamethyl-
4-isopropylcyclo-
hexene-1
c
122 to 123 67
0.8696 7
1. 48767 7
1
@ 29mm
() 17
@ 17
C [^| C
0.8799 7
\LJ<^
c | c
c-c-c
358
(1) K, v, Auwers, Ann. 420, 84, 1920.
(2) K. v. Auwers and P. EHinger, Ann. 387, 200, 1912.
(3) K. v. Auwers, R. Hinterseber and W. Treppmann, Ann. 410, 257, 1915.
(4) K. v. Auwers and F. Krollpfeiffer, Ber. 48, 1226, 1915.
(5) K. v. Auwers and E. Lange, Ann. 409, 149, 1915.
(6) K. v. Auwers and W. Moosbrugger, Ann. 387, 167, 1912.
(7) K. v. Auwers and G. Peters, Ber. 43, 3111, 1910.
(8) R. F. Bacon, Philippine J. Sci. 3, 49, 1908.
(9) A. Baeyer, Ann. 278, 88, 1894.
(10) A. Baeyer, Ber. 26, 820, 1893.
(11) E. Bergmann and F. Bergmann, J. Am. Chem. Soc. 59, 1443, 1937.
(12) D. Bodroux, Ann. chim. [10] 11, 511, 1929.
(13) J. W. Bruhl, Ber. 25, 142, 1892.
(14) J. W. Bruhl, J. prakt. Chem. [2] 49, 201, 1894.
(15) E. P, Carr and H. Stucklen, J. Chem. Phys. 6, 55, 1938.
(16) G. Chavanne and B. v. Roelen, Bull. soc. chim. Belg. 22, 410, 1908.
(17) G. Chiurdoglu, Bull. soc. chim. Belg. 47, 241, 1938.
(18) A. Cotton and H. Mouton, Ann. chim, phys. [8] 28, 209, 1913.
(19) A. W. Crossley and C. Gilling, J. Chem. Soc. 97, 2218, 1910.
(20) A. W. Crossley and N. Renouf, J. Chem. Soc. 87, 1487, 1905.
(21) F. Ebel, R. Brunner, and P. Mangelli, Helv. Chim. Acta 12, 19, 1929.
(22) F. Eisenlohr, Fortschr. Chem. Physik. 18, No. 9, 1, 1935.
(23) G. Elliott and R. P. Linstead, J. Chem. Soc. 1938, 660.
(24) J* F. Eykman, Chem. Weekblad, 4, 41, 1907.
(25) J. F. Eykman, Chem. Weekblad 6, 699, 1909.
(26) E. B. Evans, J. Inst. Petroleum Tech. 24, 321, 1938.
(27) W, F. Faragher and F. H. Garner, J. Am. Chem. Soc. 43, 1715, 1921.
(28) W. F. Faragher, W. A. Gruse, and F. H. Garner, Ind. Eng. Chem. 13, 1044, 1921.
(29) A. Favorsky and I. Borgmann, Ber. 40, 4863, 1907.
(30) E. C. Fortey, J. Chem. Soc. 73, 932, 1898.
(31) M, Godchot, Bull. soc. chim. [5] 1, 1153, 1934.
(32) M. Godchot and P. Bedos, Compt. rend. 181, 919, 1925.
(33) M. Godchot and G. Cauquil, Compt. rend. 191, 1326, 1930.
(34) M. Godchot and G. Cauquil, Compt. rend. 206, 88, 1938.
(35) M. Godchot, M. Mousseron, and R. Granger, Compt. rend. 198, 480, 1934.
(36) G. A. C. Gough, H. Hunter, and J. Kenyon, J. Chem. Soc. 1926, 2052.
(37) C. Harries and R. Seitz, Ann. 395, 253, 1913.
(38) C. Harries and R. Weil, Ber. 37, 845, 1904.
(39) W. N. Haworttr, J. Chem. Soc. 103, 1242, 1913.
(40) C. Hell and O. Schaal, Ber. 40, 4162, 1907.
(41) G. G. Henderson and R. Boyd, J. Chem. Soc. 99, 2159, 1911.
(42) G. G. Henderson and T. F. Smeaton, J. Chem. Soc. 117, 144, 1920.
(43) D. C. Hibbit and R. P. Linstead, J. Chem. Soc. 1936, 470.
(44) W. Httckel, K. Kumetat, and H. Severin, Ann. 518, 184, 1935.
(45) V. N. Ipatieff, Ber. 43, 3383, 1910.
(46) V. N. Ipatieff, Ber. 45, 3205, 1912.
(47) A. Juery, Bull, soc, chim. [4] 17, 167, 1915.
(48) F. W. Kay and W. H. Perkin, J. Chem. Soc. 87, 1066, 1905.
(49) B. A. Kazansky and N. Glushnev, J. Gen. Chem. (U.S.S.R) 8, 642, 1938.
(50) E. Knoevenagel, Ann. 297, 113, 1897.
(51) S. Komatsu and T. Kawamoto, J. Chem. Soc. Japan 52, 685, 1931.
(52) L Kondakow and E. Lutschinin, J. prakt. Chem. [2] 60, 257, 1899.
359
(53) I. Kondakow and J. Schindelmeiser, J. prakt. Chem. [2] 61, 477, 1900.
(54) P. A. Levene and S. A. Harris, J. Biol. Chem. 112, 195, 1935.
(55) W. Louguinine, Compt. rend. 150, 915, 1910.
(56) A. Mailhe* and M. Murat, Bull soc. chim. [4] 7, 1083, 1910.
(57) A. Mailhe* and M. Murat, Bull. soc. chim. [4] 9, 464, 1911.
(58) R. Majima and B. Kubota, Japan J. Chem. 1, 19, 1922.
(59) W. Markownikow, Ann. 302, 1, 1898.
(60) W. Markownikow, Ann, 336, 310, 1904.
(61) W. Markownikow, J. Russ. Phys. Chem. Soc. 35, 389, 1903.
(62) W. Markownikow, J. Russ. Phys. Chem. Soc. 36, 58, 1904.
(63) W. Markownikow and W. Tscherdynzew, J. Russ. Phys. Chem. Soc, 32, 302, 1900.
(64) H. Meerwein, Ann. 405, 129, 1914.
(65) H. Meerwein and C. Fleischhauer, Ann. 417, 263, 1918.
(66) B. N. Menschutkin, J. Russ. Phys. Chem. Soc. 44, 1137, 1912.
(67) B, Mereshkowsky, J. Russ. Phys. Chem. Soc. 45, 1940, 1913.
(68) M. Murat, Ann. chim. phys. [8] 16, 108, 1909.
(69) S. S. Nametkin, J. Russ. Phys. Chem. Soc. 55, 47, 1923-24.
(70) S. S. Nametkin and L. J. Brussoff, Ber. 56, 1807, 1923.
(71) S. S. Nametkin and L. J. Brussoff, J. Russ. Phys. Chem. Soc. 55, 75, 1924.
(72) S. S. Nametkin and A. Jarseff, Ber. 56, 1803, 1923.
(73) J. B. Niederl and R. A. Smith, J. Am. Chem. Soc. 59, 715, 1937.
(74) W. H. Perkin Jr. through E. C. Fortey, J. Chem. Soc. 73, 943, 1898.
(75) W. H. Perkin Jr. and G. Tattersall, J. Chem. Soc. 87, 1083, 1905.
(76) H. Pines and V. N. Ipatieff, Unpublished data.
(77) J. Read and A. J. Watters, J. Chem. Soc. 1929, 2165.
(78) A. H. Richard, Compt. rend. 153, 116, 1911.
(79) W. A. Roth and K. v. Auwers, Ann. 407, 145, 1915.
(80) L. Ruzicka, D. R. Koolhaas, and. A. H. Wind, Helv. Chim. Acta 14, 1151, 1931.
(81) L. Ruzicka and E. Peyer, Helv. Chim. Acta 18, 676, 1935.
(82) P. Sabatier and A. Mailhe", Ann. chim. phys. [8] 10, 527, 1907.
(83) P. Sabatier and A. Mailne", Bull. soc. Chim. [3J 33, 74, 1905.
(84) P. Sabatier and A. Matlh, Compt. rend. 138, 1321, 1904.
(85) P. Sabatier and A. Maiihe", Compt. rend. 140, 350, 1905.
(86) P. Sabatier and A. Mailhe*, Compt. rend. 141, 20, 1905.
(87) P. Sabatier and A. Mailh, Compt. rend. 142, 437, 1906.
(88) P. Sabatier and J. B. Senderens, Compt. rend. 134, 1130, 1902.
(89) Schimmel and Co., Ber. Akt. 1911, 128.
(90) W. Schrauth and K. Quasebarth, Ber. 57, 854, 1924.
(91) F. W. Semmler, Ber. 34, 3122, 1901.
(92) F. W. Semmler, Ber. 36, 1033, 1903.
(93) F. W. Semmler, Ber. 42, 522, 1909.
(94) F. W. Semmler, "The Ethereal Oils," Leipzig, 1906, Vol. 3, p. 38,
(95) J. B. Senderens, Compt. rend. 154, 1168, 1912.
(96) Shin-ichiro Fujise, Sci. papers Inst. Phys. Chem, Res. Tokyo 8, 185, 1928.
(97) Shin-ichiro Fujise, Sci. papers Inst. Phys. Chem. Res. Tokyo 10, 83, 1929.
(98) F. K. Signaigo and P. L. Cramer, J. Am. Chem. Soc. 55, 3326, 1933.
(99) A. Skita and A. Schneck, Ber. 55, 144, 1922.
(100) P. Subow, J. Russ. Phys. Chem. Soc. 45, 242, 1913.
(101) F. Tiemann and F. W. Semmler, Ber. 26, 2708, 1893.
(102) M. Tiffeneau, Compt. rend. 146, 1153, 1908.
(103) W. Treibs and H. Schmidt, Ber. 61, 459, 1928.
(104) L. Tschugaeff, Z, physik. Chem. 76, 469, 1911.
360
(105) L. C. Urban and E. Kremers, Am. Chem. J. 16, 395, 1804.
(106) G. Vavon, Compt. rend. 152, 1675, 1911.
(107) A. I. Vogel, J. Chem. Soc. 1938, 1323.
(108) R. L. Wakeman, Thesis, Mass. Inst. Tech. 1930.
(109) O. Wallach, Ann. 289, 337, 1895.
(110) O. Wallach, Ann. 323, 135, 1902.
(111) O. Wallach, Ann. 347, 316, 1906.
(112) 0. Wallach, Ann. 359, 287, 1908.
(113) 0. Wallach, Ann. 381, 51, 1911.
(114) O. Wallach, Ann. 396, 264, 1913.
(115) O. Wallach, Ber. 35, 2822, 1902.
(116) O. Wallach and L. Augspurger, Ann. 396, 281, 1913.
(117) O. Wallach and L. Augspurger, Ann. 414, 212, 1918.
(118) O. Wallach and L. Augspurger, Nachr. kgl. Ges. Gottinger, 1915, 1.
(119) O. Wallach and J. B. Churchill, Ann. 360, 72, 1908.
(120) O. Wallach, J. B. Churchill, and M. Rentschler, Ann. 360, 55, 1908.
(121) O. Wallach and E. Evans, Ann. 360, 44, 1908.
(122J O. Wallach and W. Kempe, Ann. 329, 82, 1903.
(123) 0. Wallach and H. Mallison, Ann. 360, 68, 1908.
(124) O. Wallach and P. Mendelsohn-Bartholdy, Ann. 360, 48, 1908.
(125) O. Wallach and H. Schlubach, Ann. 396, 283, 1913.
(126) I. Wanin, J. Russ. Phys. Chem. Soc. 44, 1072, 1912.
(127) H. I. Waterman and H. A. van Westen, Rec. trav. chim. 48, 637, 1929.
(128) J. Zelikow, Ber. 37, 1374, 1904.
(129) N. D. Zelinsky, Ber. 35, 2488, 1902.
(130) N. D. Zelinsky, Ber. 57, 2055, 1924.
(131) N. D. Zelinsky and A, I. Gorsky, Ber. 41, 2630, 1908.
(132) N. D. Zelinsky and A, I. Gorsky, J. Russ. Phys. Chem. Soc. 40, 1399, 1908.
(133) N. D. Zelinsky and J, Gutt, J. Russ. Phys. Chem. Soc. 38, 476, 1906.
(134) N. D. Zelinsky, K. Packendorff, and E. G. Chochlowa, Ber. 68, 98, 1935,
(135) N. D. Zelinsky and G. Pawlow, Ber. 57, 1066, 1924.
(136) N. D. Zelinsky and J. Zelikow, Ber. 34, 3249, 1901.
361
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
D?
n 2
Additional Data
Cycloheptene
us
0.8253
1.457 4
- -000088 rC
(Suberene)
114.5 to 115 l
0.7884 10
1.45301 4
dl (0 to 65)
dn
@ 774mm
62.1
1.4545 8
O.
US 12
0.7885 1
1.4552 7
di (13 to 20)
114.5 to
62.0
1.45737"
115 8 -
0.8052 10
1.4585 9
114 to 115 12
42.1
1.4512 9
113 tollS 7
0.8059 10
113 tollS 8
41.4
1.4607 1 - 8
@ 752mm
0.8228 7
@ 13.5
112 to 114
0.823
1. 45450 10
<& 720mm
0.8239 s
20
H *
0,8254 9
0.8255 10
1.46438"
20.0
H
0.8245 '
ft
D
1.46966"
0.814'
y
19
0.8272 10
@ 17.9
0.8359 .
n 13.6
'^13.6
0.8407
CgH.14
1-Methylcyclo-
138
0.826 2
1.458
=~00010 6 /C
heptene-1
dt (10 to 25)
c
137.5 to
0.8243
1.4575 9
138.5
22
@22
137 to 138 2
0.824 ll
1,4581"
133 to 135
19.5
19.5
@ 720mm
0.8294 2
1.4581*
74 to 75
15
@ 15
100mm
0.8350 ''
l.4604'
*
13.5
362
Name and Carbon Skeleton
M. P.,*C.
B. P., C.
@ 760mm
!>!'
nl
Additional Data
1,4,4-Trimethyl-
cycloheptene-1
(Eucarvene)
161 to 165
0.8185
1.4561
@ 720mm
C
1
Q.
1
C
(1) M. Godchot, Bull. soc. chim. [5] 1, 1153, 1934.
(2) M. Godchot and P. Bedos, Compt. rend. 184, 208, 1927.
(3) M. Godchot and G. Cauquil, Compt. rend. 191, 1326, 1930.
(4) C. Harries and L. Tank, Ber. 41, 1701, 1908.
(5) W. Markownikow, J. prakt. Chem. [2] 49, 409, 1894.
(6) W. Markownikow, J. Russ. Phys. Chem. Soc, 25, 550, 1893.
(7) N. A. Rosanov, J. Russ. Phys. Chem. Soc. 48, 309, 1916.
(8) N. A, Rosanov, Tyazhelov, and Nikiforov, J. Russ. Phys. Chem. Soc. 61, 2313, 1929.
(9) L. Ruzicka and C. F. Seidel, Helv. Chim. Acta 19, 424, 1936.
(10) A. I. Vogel, J. Chem. Soc. 1938, 1323.
(11) 0. Wallach, Ann. 345, 139, 1906.
(12) R. Wfflstatter, Ann. 317, 204, 1901.
363
Name and Carbon Skeleton
M. P. t C
B. P. t
@ 760mm
tif
B
Additional Data
Cyclooctene
1.468,
145 to 146
0.8415
1.4678
143 to 144
0.855
1.4736 9
145
0.8486 ft
1.4739'
@ 730mm
@19
1.4683 *
140 to 142 *
0.8487 >
@17
@ 720mm
@17
1.4700 2
0.8497 2
@13.5
^isis
1.4787 *
0.871
w "; 5
@0
1.4767*
M t8.5
^'.
1.4759*
1.4670 6
*r
1.4814
t .4703 6
W 18.5
*!/
1-Methylcyclooctene-l
c
158 to 160 l
0.8487
1.4691
165 to 169
0.8515 l
1.4673 1
@ 730mm
@15
@ 15
0.8525 2
1.4720 2
T\13.5
13.5
364
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
S
Additional Data
Cyclopentadecene
36 to 37 6
122 to 123 8
0.8416 6
1.4728 5
@ 1.2mm
@ 68.5
0.8429 *
@ 66.5
'L b
1.4791 5
1.4710 6
w //
1.4703*
w !/
1. 4765*
(/
1 .4620 5
s. r
1.4682 8
1.4753 5
V
1.4816 6
^52.4
^%
1.4651
1.4713 5
y
1-Methylcyclopenta-
decene-1
152 to 153 7
0.8697 7
1.4853 7
@ 12mm
@22
@22
365
Name and Carbon Skeleton
M. P.,C.
B, P., C.
(m 760mm
/?r
2
Additional Data
1-Methylcyclopenta-
decene-2 or -3
Ma --8.8"
(Mnscene)
120(ol1mm 4
*/ 17X11*
Cycloheptadecene
(Civetene)
47 8
115*
@ 3mm
(1) M. Godchot and G. Cauquil, Compt. rend. 185, 1202, 1927.
(2) M. Godchot and G. Cauquil, Compt. rend. 191, 1326, 1930.
(3) N. A. Rosanoff, J. Russ. Phys. Chem. Soc. 61, 2313, 1929.
(4) L. Ruzicka, Helv. Chira. Acta 9, 715, 1926.
(5) L. Ruzicka and H. A. Boekenoogen, Helv. Chim. Acta 14, 1319, 1931.
(6) L. Ruzicka and W. Brugger, Helv. Chim. Acta 9, 399, 1926.
(7) L. Ruzicka, H. Schinz, and M. Pfeiffer, Helv. Chim. Acta 11, 686, 1928.
(8) L. Ruzicka, H. Schinz, and C. F. Seidel, Helv. Chim. Acta 10, 695, 1927.
(9) R. Willstatter and E. Waser, Ber. 43, 1176, 1910; 44, 3423, 1911.
C,H,, 366
2. CYCLENES WITH AN ALKENYL OR OLEFIN SUBSTITUTION, C.H.,
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
y
Additional Data
1-Ethenylcyclo-
pentene-1
c=c
114 to 115 90
0.824
1.4870 90
6
@ 754mm
1-Propen-l-ylcyclo-
pentene-1
c=c-c
142 to 144 90
0.835 M
1.4865 90
6
@ 754mm
CgXlu
1-Buten-l-ylcyclo-
pentene-1
c=oc-c
59 to 62
0.833 M
1.4850 M
6
@ 14mm
367
C,H,<
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
Iff
S
Additional Data
l-Methyl-2-isopropen-
ylcyclopentene-1
c
C |
155 to 157 84
0.85 15 *
1.4892 M
1 -Methyl-3-isopropen-
ylcyclopentene-1 or -5
o c
150 w
c=c oc
1 1
c c
3-Methyl-4-isopropen-
ylcyclopentene-1
/%s
143 to 145 M
@ 770mm
c=c c
1
1
c
368
Name and Carbon Skeleton
M, P.,C
B. P., C.
(<u> 76()mm
D?
M i'n
H D
Additional Data
3-Methyl-l-buten-3-
ylcyclopentene-x
c-oc=c
168 to 169 21
0.8377 2l
1.4665 21
@ 18.5
^ 18.5
X
c
d-3-Methylene-4-
methyl-5-isopropyl-
cyclopentene-1
c
169 to 173 80
1.470 80
1
c-c ^
50 to 54 80
v>
@ 10mm
/H
C C
2,3,3-Trimethyl-4-
ethenylcyclopentene-1
c
157 to 158 I2
CY
/M-
c=c c
369
Name and Carbon Skeleton
M, P.,C.
B. P., C.
760mm
Iff
4
Additional Data
2,3,3-Trimethyl-4-iso-
propenylcyclopentene-1
c
177 to 179
(_) x
@ 754mm
c=c c
1
1
c
2-Methyl-l-(2,3,3-tri-
methylcyclopenten-1-
yl)-propene-l
c
188 to 190 ll
0.8311 "
1.46707 "
1
c=c-c
0.8421
@16
c
\s 14 Jtl.24
2-Ethyl-l-(2,3,3-tri-
methylcyclopenten-1-
yl)-butene-l
c~c
222 to 224
0.8688 n
1.46875"
1
oc-c-c
6C
@19
0.8814 "
'
@0
r-
c
370
Name and Carbon Skeleton
M. P.,C.
B. P., C.
(& 760mm
^
W D
Additional Data
1-Ethenylcyclohexene-l
6
145 18
143 to 145 43
36 @ 23mm "
0.8701
n 20
JJo
0.8523
@16
0.8862
1.49060"
1.4677"
@16
1.46423"
n l *
Z>S
1,48812"
"B.
4-Ethenylcy clohexene- 1
130
0.83 10 M
1.46529"
dt (0 to 20)
@ 773mm
0.8320 63
@20.1
129.5 to
130.5 "
0.8484
1. 46380
o=c
65 to 66
@ 100mm
50 @ 50mm
3-Methylene-l-methyl-
cyclohexene-1
c
r"S
134 to 138 B
0.8389 8
@ 18.8
1.48723 8
1. 48274 8
<A
1. 49872*
1.50910 B
y
371
Name and Carbon Skeleton
M. P.,C
B. P., C.
(r/j 760mm
D?
J
Additional Data
3-Methylene-2-methyl-
cyclohexene-1
c
r'^v'
135.5 36
0.8521
1 .4925 35
c
l-Cyclohexen-l-yl-
propene-2
or
1-Cyclohexylidene-
propene-2
c-c=c c-c=c
159 to 161 77
0.8457 77
1 II
O^^NW
0.8468 "
r (l
D ZQ
k^
0.861 1 77
@,0
l-Propen-2-ylcyclo-
hexene-1
c-oc
6"
158 to 159 54
0.8426 "
1.477 64
@ 755mm
372
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Jff
<
Additional Data
1-Isopropenylcyclo-
hexene-1
oc-c
6
161 to 162 M
l T Methyl-2-ethenyl-
cyclohexene-1
c
6OO
'
156 to 157 18
l-Methyl-4-ethylidene-
cyclohexene-1
or
l-Methyl-4-ethenyl-
cyclohexene-1
c c
1 1
O^xW
160 to 163 10
0.843 10
@22
1. 47586 10
@22
"O
II \
373
C,H U
Name and Carbon Skeleton
M p r
ML . JT . f \s .
B. P., C.
@ 760mm
pj
B
Additional Data
1 ,5-Dimethyl-3-meth-
ylenecyclohexene-1
c
61 to 66
0.8280 *
1.4809*
@37mm
@20.1
@ 20.2
54 to 56 8
0.8300 8
1.48151 - 8
@ 25mm
@17.1
1.47653 8
c c
n^- 2
1.49168
1.50159
M 20.2
x
l-Buten-3-ylcyclo-
hexene-1
c-c-c=c
60 to 62
0.8445
1.4745"
6
@ 10mm
@18
2-Methyl-l-cyclo-
hexen-l-ylpropene-1
c
172 to 173 86
0.8537
1.4854 8S
1
o=c-c
6
88 to 90
@ 13mm
374
Name and Carbon Skeleton
\r nor*
M. Jr., L.
B. P., C.
@ 760mm
Iff
*5
Additional Data
2-Methyl-l-cyclo-
hexen-l-ylpropene-2
c
1
0.8607 36
1.4797"
oc=c
1
l-Methyl-2-isopropen-
ylcyclohexene-1
(o-Menthadiene)
177 44
@ 755mm
.
C
c 1
JL c=c
d-l-Methyl-3-isopro-
penylcyclohexene-1
[a] =+675 37
(Sylvestrene, carvestrene)
176 to 177 M
175 to
0.8470 94
0.848 w
1.4752 37
1.47573"
[ajto^ +66.32"
C
! 78 37 ,93
0.8485
1. 47799 M
175 to 176"
@ 18
@18
173 to 175 3
0.85 10 94
1. 47468 M
\
@16
**.
c=c
0,8612 3
1
ffii 1 ft
c
\J lu
375
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
iff
s
Additional Data
M-Methyl-3-isopro-
[a] =-68.2
peny Icy clohexene- 1
176 to 178 37
0.848 w
1.4761"
19
(/M-Methyl-3-isopro-
peny Icy clohexene- 1
177 to 179 7
0.8453
1. 47506
@ 769mm
0.8486
1.47717 7
177.2 to
@17.2
17.2
178.2 7
1. 47380 7
@ 767.5mm
M //' 2
176 to 177.5 7
@ 764mm
1. 48505 7
w^- 2
!7 9 24
178 10
1. 49245 7
175 to 180 3
wj 7 -*
174 to 177.5 l
173 to 175 M
178 to 179
@ 750mm
C to fin
376
Name and Carbon Skeleton
M. P.,C.
B. P., C;
@ 760mm
*
ng
Additional Data
l-Methyl-4-isopropyli-
denecyclohexene-1
(^-Menthadiene)
(Terpinolene)
186 40
@ 764mm
0.854 M
0.857
1.48017
1.484"
C
185 to 190 w
184 to 188 "
0.8583
0.8633 40
184 to 187
Z/15
183 to 185
181 to 185 M
OC-C
121 8S
@ 112mm
75 @ 15mm 40
72 @ 10mm 40
67 to 68
@ 10mm
d-l-Methyl-4-iso-
propenylcyclohexene-1
[]g- + 100.2 t
[]. + 1 26.84 13
(^-Menthadiene)
(d-Limonene)
-96.6 M
180 to 182 4
@ 765mm
0.7135 79
@ 176.5
1,4681 17
@30
[lg-+ 122,47"
C
175.5 to 176"
@ 763mm
0.8356
@30
1.4720 27
[ajg- 8 - 4- 104.25 14
f^l
179.5 to
180.5 4
0.8417"
@25
1.4725 "
[a] D -+124
c-oc
178 to
179 so
178
0.8409 "
@25
0.8437 60
1.47428 14
@21
1.4727
W^-H- 123.6 2e
[a] II -+122.7
177.6 to
178.0 7
Dll
0.8402 14
@ 19.6
1.473"
[a^-^ 120.466
176^177.4'
176 to 177 17
176tol76.7 l
176 to 176.4 1
176 W
175 to 177 M
0.8425 80
0.8456 4
0.846 w
0.8441
DB
1.4771
1.49116 4
@ 13.4
1.47124 14
fAverage of several
experimental values.
175
0.8425 7
174 to 176
@ 19.6
377
Name and Carbon Skeleton
TUT P r t
.M. JT .) L-.
3. P., C.
@ 760mm
iff
<
Additional Data
d-l-Methyl-4-iso-
propenylcyclohexene-1
(Continued)
177.5 30
0.8464 4
1.48342*
759mm
@18
n X a
177.6to
0.8532 60
1. 47489 7
177.8 73
@ 15.6
w //' 7
@ 755mm
0.8498 eo
a
176.5 79
n u
/^15
1.48658*
753.7mm
0.8468 7
M//
177 30
@14.7
1.48223 "
@ 745mm
0,8532 fl
^
71 @ 20mm 59
D 10
1.49796*
64.4 n
@ 15mm
0.8530 79
^
1.48277 *
0.8576
>7 14.7
H
0.8584 80
1.50109*
@0
n "p
0.8585 80
1. 48886 ! *
Dl
w //,
1.50739*
7
1. 49062 7
H /}' 7
1.51031 *
n \:\A
378
Name and Carbon Skeleton
M.P..-C.
B. P., C.
@ 760mm
*
-g
Additional Data
M-Methyl-4-iso-
propenylcyclohexene-1
^jw.e^^ 101.5 "
(/-Limonene)
175.5 to
0.8453 w
1.47468 "
176.5 "
@ 763mm
176 to 176.4 13
Z/25
0.8417 73
@ 20.6
@ 20.5
1.47459*
1.4727 73
[a]^-- 103.51 M
175.5 to 177
0.8407 "
@ 17.2
175 to 176 w
@ 20.5
1.4740 73
177.6 to
0.8422 1S
@ 14
177.8
@ 755mm
0.846 96
0.8483 M
1.47157"
64.4
@ 15mm
D 20
UZQ
0.85 14 M
1.48256"
n 15
1.48924"
0.8472 73
n*
0.8549 60
n 10
dH-Methyl-4-iso-
propenylcyclohexene-1
(<f/-Limonene)
(Dipentene)
175.5 to
176.5 "
0.7962 22
@78.3
1.47443 14
@ 20.85
@ 763mm
0.8486
1.47194 27
180 to 182 M
n 88
X/25
1.4746
180 to 181"
0.8402 "
1. 47644 M
178 to 180
@ 20.85
1.4727
! 78 75 ,94
0.844
@18
177 M
0.845 4 - M - 9
1.48013 "
176 to 178
0.8535 19
@16
175 to 178
0.8450
1.44279 22
175 to 176"
@16.6
ng-
174 to 1 75
0.8548
1.47134"
64.4"
@ 15mm
D 18
0.85457
14.4
5-~
1. 47308 M
a
379
C io HI a
Name and Carbon Skeleton
M. P.C.
B. P., C.
760mm
Iff
-B
Additional Data
dM-Methyl-4-iso-
propenylcyclohexene- 1
(Continued)
0.8627
1.47172*
D\
w}}-*
0.8657
1.47056"
a
1.45328*
1.48231 M
1.48291*
w lfl.6
1. 48629
1.45965"
^78.3
1.48898"
^20. 86
1.48961 *
W /J' 6
1. 49367
"y
2-Methyl-3-iso-
propenylcyclohexene-1
(o-Menthadiene- 1 ,80)
170 to 171 fl2
0.8481
1.4758
C
@ 765mm
n 20
^20
c=c
1
c
380
Name and Carbon Skeleton
M. P.,C
B. P., C
@ 760mm
z>r
y
Additional Data
2-Methyl-4-iso-
propenylcyclohexene-1
(w-Menthadiene- 1 ,8a,
176 to 177 24
0.8481 2 - M
1.49660 s
Isocarvestrene, Diprene)
@ 765mm
0.8476 *
@r 23.4
171.5 to 173 2
0.8496 2 *
1. 46946 s
C
a
@ 752mm
68.5 to 69 2
@ 16mm
/>lo
1.47799"
1.49090"
1.49893"
c-oc
d-3-Methyl-l-iso-
propenylcyclohexene-1
(w-Menthadiene)
181 M
0.864
1.4946 .
[k-+64.0 38
@ 736mm
^!?
179 w
@ 730mm
C
/-3-Methyl-l-lsopro-
penylcyclohexene-1
H.--."-
181 to 182 H
1.4972"
381
Name and Carbon Skeleton
\r n or*
<UaLt JT, t U.
B. P., C.
760mm
*
s
Additional Data
d/-3-Methyl-l-isopro-
penylcyclohexene-1
182 to 183 38
0.8549
@ 770mm
@22
1.5015 29
187
0.8609 w
@25
@ 765mm
D 20
1.4975 M
181 to 182 M
0.8624 M
1.S030*
184
D 80
@ 745mm
3-Methyl-4-iso-
propenylcyclohexene-1
(o-Menthadiene)
170 to 171
0.8490"
1.4778"
@ 765mm
D 17
,\
c=c-c
d-3-Methyl-5-iso-
Mg-+29.6
propenylcyclohexene- 1
c*\
175 to 176"
oc c
1
c
382
Name and Carbon Skeleton
M. P.,C.
B. P., C.
(ft) 760mm
D
s
Additional Data
M-Methyl-5-iso-
l]^=:~25.3
propenylcyclohexene-1
175 to 176 >
dl-3-Methyl-S-iso-
propenylcyclohexene-1
175 to 176
@ 765mm
3~Methylene-6-iso-
propylcyclohexene-1
[^=4-18.54^
[!,,=+ 17.60
(-Menthadiene,
171tol72 9
0.8520
1.4788 25
0-Phellandrene)
@ 766mm
0,8558
171 to 172
10
C
1
57 @ llmm 26
c-c
^\
C
383
Name and Carbon Skeleton
M. P.,C.
B. P., C.
(fj\ 760mm
X
-S
Additional Data
d-3-Methyl-6-iso-
[Jg- + 131.93
propenylcyclohexene-1
20
(/-Menthadiene)
172 to 174
0.838 20
1.4692 20
578
171 to 173 20
@22.5
@22.5
H 2 So =+ 153.4 l7
C
@ 750mm
0.8382 M
1.4697 88
1
c=c
\^x<^
@ 20.5
@ 20.5
C
1.4775 80
/-3-Methyl-(5-iso-
[a^-- 140.58 "
propenylcyclohexene- 1
__ S92 o 70
172.5 to
0.83 70 70
1. 47043 87
173.5 87
0.8390 70
1. 47643 70
172 to 172.5 70
@ 19.5
1.4750 70
@ 745mm
@ 19.5
4-Methylene-l-iso-
propylcyclohexene-1
(p-Menthadiene,
173 to 174 97
0.838 w
1.4754 97
j8-Terpinene)
@22
@22
0.840 n
1.4751 w
c-c-c
1
22
@22
II
c
C 10 Hie
384
Name and Carbon Skeleton
M. P, t C,
B. P., C.
@ 760mm
*r
Additional Data
d-4-Methyl-l-iso-
[aJ^n + 100 M
propenylcyclohexene-1
WJ5;-f 118.33
(p-Menthadiene)
184 to 185 "
0.8574
1.4957"
776mm
24
[a]J5= s "i-98.2 04ft
ooc
j
174 to 177 *
0.8679 2 *
1. 48422 M
32
184
24
1.4965 1 *
laj/; ^^
756mm
0.8420
1.4915 M
183 to 185.5 2
0.851 *>
1.4876 s0
1
755mm
0.858 M
19.8
c
182 to 184 20
0.8649
1.4966
750mm
DlS
14,2
182 to 183
@ 748mm
0.8634
69 14mm *
62 to 65 82
0.8585
14.2
@14mm
0.86483 4B
0.8712
dM-Methyl-1-iso-
propenylcyclohexene-l
184 to 185 4I
0.83579
1.46945 4 *
/i so
<Ml7.2
0.8390
1.481 13**
Z?JJ
W^' 2
0.8425
1. 48824
z?l!
ng-
7
385
Name and Carbon Skeleton
Af. P.,C.
B. P.,C.
@ 760mm
/?r
-20
n )
Additional Data
</-4-Methyl-2-propen-2-
ylcyclohexene-1
[],-+ 52.84
(o- Menthadiene)
171 to 173 7
0.8361
C-OC
0'
^^
\
c
d-4-Methyl-2-iso-
W^.+IT-S "
propenylcyclohexene-1
c
it
187
0.8609 M
1.4972 "
it
c-c
@ 765mm
n 20
L'ao
1.4975 M
r"V
181 to 182 M
[ J
179 W
V
@ 730mm
c
czs-4-Methyl-5-iso-
propenylcyclohexene-1
169 to 170
0.8507
1.4825 3
@ 762mm
n 20
1^20
c=cf |
1 c
c
380
Name and Carbon Skeleton
M. P, t C.
Bn o/~
. Jr. t L>.
@ 760mm
tif
n'*
Additional Data
/ron$-4-Methyl-5-iso-
*
propenylcyclohexene-1
170 3
0.8477
1.4749 W
D 20
l,5-Dimethyl-3-ethyli-
denecyclohexene-1
c
175 to 178
0.8360
1.4868*
@ 753mm
21.3
@ 19.9
0.8332 6
1.48092*
v
0.851 6 74
@17.7
G c-c
1.48255 e
a
1.47701
W 17.7
a
1.49748 fl
1.49070*
n l
1.50720*
H y
1.49930*
387
C, H,,
Name and Carbon Skeleton
M. P.,t
B. P., C.
(fi>> 760mm
cr
1*5
Additional Data
2,4-Dimethyl-4r
ethenylcyclohexene-1
c
O/
160 to 161"
0.8331"
1.46581"
44 @ 9 mm "
D 20
@ 19.7
0.8481 "
1.46230"
/\
D
ft 19 * 7
c oc
a
1.47204"
1.47964"
U- T
V
2,4,4-Trimethyl-3-
methylenecyclo-
hexene-1
c
48.5 to 49 60
0.843 60
1.4772 B0
X^,/
@ llmm
@21
21
/\ c
c c
l-Methyl-2-buten-3-
ylcyclohexene-1
c
| c-oc=c
75 to 78 41
@ 10mm
0.8769
@ 15.5
1.4853"
@ 15.5
388
Name and Carbon Skeleton
M. P.fC.
B. P., C.
760mm
Iff
-s
Additional Data
d-2-Methyl-l-(3-
methyl-cyclohexen-1-
yl)-propene-l
[ak- 4-54.8
c
i
192 to 193 M
0.853 1*
1.4802"
1
oc-c
A
@15
@15
0.
c
d-2-MethyM-(4-
methyl-cyclohexen-1-
yl)-propene-l
[a^^-f-63.9 ^ 5
c
I
190 to 191 3fi
0.8445 36
1.4793 36
c=c-c
I
c
4-Methyl-2-(2~methyl-
propen-2-yl)-cyclo-
hexene-1
[] D 4-68.8
c-c=c
191 to 192
0.846
1.4768
c
389
Name and Carbon Skeleton
Jlf. P.,C.
B. P., C.
@ 760mm
D?
S
Additional Data
1 -Ethy 1-4-isopropeny 1-
cyclohexene-1
c-c
1
201 to 202 w
0.8545 M
1.4802 M
c=c-c
l,2-Dimethyl-4-iso-
propenyl-cyclohexene-1
or
2,3-Dimethyl-5-iso-
propenyl-cyclohexene-1
[]g-- 55.44 '*
|a]g- -47.55 7 *
c
| c c
f^ or r"Y
]
72 @ 9mm 74
0.8576 74
1. 46502 "
^^ /^s*\
I c-c c
c-c=c ||
c
l,3-Dimethyl-4-iso-
propylidene-cyclo-
hexene-1
[Jg- 96.89 7
[a]g- -81.41 7fi
c
71 to 73 76
0.8402 76
1.47252 7
rS
@ 16mm
II c
c-c-c
Cu Hlg
390
Name and Carbon Skeleton
M. P.C.
B, P., C.
@ 760mm
D?
-B
Additional Data
l,5-Dimethyl-3-iso-
propylidene-cyclo-
hexene-1
c
191 to 196
106 to 109
0.8561
@23.6
1.49367*
@23.2
. X
c c-c
1
c
@46mm
99 to 103
@36mm
0.8465 6
@22.4
0.8395
@21.4
0.8448
1.49519
1.48521
1. 48559
@ 19.0
@18.0
1. 48938
n u
a
1. 49072
a
1 48119 6
n n'
a
1. 48168
1. 50466
n 'u'l
1. 50674
rift*
1.49516*
1.49564*
1.51473*
y
1.51716*
1.50412
1.50450
wg-
391
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
s
Additional Data
2,4-Dimethyl-4-propen-
2-ylcyclohexene-l
c
182 to 185 *
0.8415 M
1. 47292 84
Q 7
183 to 185 81
@ 16
@ 16
@ 741mm
0.8450 3l
1.47281 31
67 to 69 51
@9.9
@9.9
c c-c=c
@ 9mm
0.8525
3 ,5-Dimethyl-5-iso-
propenyl-cyclohexene-1
c
184 to 186 n
0.8585 71
1.4845 71
An
@ 737mm
25
25
/^XxA
c c
5,5-Dimethyl-3-(2-
methylpropen-1-yl)-
cyclohexene-1
^.
195 to 196 48
0.8246 48
1.4653 48
C [ ^
@23
@23
c oc-c
1
1
c
392
Name and Carbon Skeleton
\f p o/-
H. f , t L-.
B. P., C.
@ 760mm
DT
B
Additional Data
3-Methyl-5-ethyl-5-iso-
propenylcyclohexene-1
c
199 to 202 7l
0.8631 n
1.4854 71
C J^ S^*}
@ 759mm
25
25
\L J
83 to 85 71
/^V^^N,
@ 15mm
oc c
1 ,2,4-Trimethyl-4-iso-
prppenylcyclohexene- 1
c
202 to 203 M
0.85322 72
1.47786 72
JL/
@ 761mm
@25
@25
\\
205"
0.8597
1.48074"
v
205"
20
@ 19.7
x\
@ 750mm
0.8626 M
1.4823
c c=c
i
97 to 98"
@16
@16
1
C
@ 22mm
0.872 7a
1.47463 72
85 @ 13mm "
@0
W "
0.8741
1.47716"
1.48572"
"B,
1.48796"
1.49241 "
n*
t
1.49491 "
y
393
Name and Carbon Skeleton
jjf p o/-
JxL. Jr. t U.
B. P., C.
@ 760mm
iff
<
Additional Data
x,x,2-Trimethyl-4:-iso-
propenylcyclohexene-1
(Dimethyl diprene)
200.5 to
201.3 2
0.8535 2
1.47915 a
@ 758mm
87.8 to 88.3 2
@12mm
C/ 13X122
c?-4-Methyl-2-propen-2-
yl-1-isopropylcyclo-
hexene-1
H^=+ 50.86 78
c-c-c
| c-c=c
O/
214 to 217 78
97 to 100 78
0.8551 78
@ 17mm
c
3-Methyl~5-n-propyl-
5-isopropenylcyclo-
hexene-1
c-c-c \^\
104 to 106 71
@ 14mm
0.8872 n
@25
1.4865 ?l
@25
c-c c
II
II
c
394
Name and Carbon Skeleton
Mn o/~
. r. t C.
B. P., C.
@ 760mm
tif
<
Additional Data
2,4,4-Trimethyl-3-
buten-1-ylcyclo-
hexene-1
c
220 to 22 1 47
0.8530 47
1.4784 47
rY
@ 747mm
^^\
/\ c=c-c-c
c c
1 ,3,3,5,S-Pentamethyl-
4-isopropenylcyclo-
hexene-1
c
122 to 1 23
0.8696 58
1. 48767 68
1
@ 29mm
@ 17
17
C (^ C
0.8799 58
Vxxx
@0
c | c
c=c-c
C 16X126
3-Methyl-6-(l,5-di-
methylhexen-4-yl)-
cyclohexene-1
Ma-- 37'"
(Dihydrozingiberene)
135 to 136 7
0.8557 8)
1.4837 81
C C
1 1
c-c=c-c-c~c
@ 15mm
122 to 125"
@ 7mm
0.865 76
1.4881 78
^sX^\
c
395
(1) O. Aschan, Ann. 461, 1, 1928.
(2) O. Aschan and P. Krohn, Ber. 57, 1959, 1924.
(3) A. Atterberg, Ber. 10, 1202, 1899.
(4) K. v. Auwers, Ber. 42, 2424, 1909.
(5) K. v. Auwers and F. Eisenlohr, J. prakt. Chem. [2J, 84, 1, 1911.
(6) K. v. Auwers and G. Peters, Ber. 43, 3076, 1910.
(7) K. v. Auwers, W. Roth, and F. Eisenlohr, Ann. 373, 267, 1910.
(8) K. v. Auwers and W. Treppman, Ber. 48, 1207, 1915.
(9) R. Bacon, Philippine J. Sci. 4A, 93, 1909.
(10) A. Baeyer, Ber. 27, 3488, 1894.
(11) A. Belial, Bull. soc. chim, [3] 31, 461, 1904.
(12) L. Bouveault and G. Blanc, Compt. rend. 136, 1460, 1903.
(13) J. v. Braun and G. Lemke, Ber. 56, 1562, 1923.
(14) J. Bruhl, J. Chem. Soc. 91, 115, 1907.
(15) R* Charlton and A. Day, Ind. Eng. Chem. 29, 92, 1937.
(16) T. Chou and W. Perkin, J. Chem. Soc. 99, 530, 1911.
(17) A. M. Clover, Am. Chem. J. 39, 613, 1908.
(18) J. Cook and C. Laurence, J, Chem. Soc. 1938, 58
(19) M. Delepine, Bull. soc. chim. [4] 7, 468, 1910.
(20) J Doeuvre, Bull. soc. chim. [4] 53, 170, 1933.
(21) K. D. Errington and R. P. Linstead, J. Chem. Soc. 1938, 666.
(22) J. F. Eykman, Chem. Weekblad 4, 41, 1907.
(23) E. Farmer and R. Pitkethly, J. Chem. Soc. 1938, 11.
(24) F. Fisher and W. Perkin, Jr., J. Chem. Soc. 93, 1876, 1908.
(25) L. Francesconi and E. Sernagiotto, Atti accad. Lincei 20, I, 329, 1911.
(26) E. Gildemeister and F. Hoffmann, "The Ethereal Oils," 1899, 172.
(27) E. Gildemeister and F. Hoffmann, "The Ethereal Oils," Vol. 1, 329, 1928.
(28) M. Godchot and G. Cauquil, Compt. rend. 204, 733, 1937.
(29) M. Godchot and G. Cauquil, Compt. rend. 206, 88, 1938.
(30) E. Godlewsky and Roshanoivitsch, J. Russ. Phys. Chem. Soc. 31, 201, 1899.
(31) V. Grignard, Ann. chim. [7] 24, 433, 1901.
(32) W. Grubb and J. Read, J. Chem. Soc. 1934, 242.
(33) C. Harries, Ann. 383, 157, 1911.
(34) W. Haworth, J. Chem. Soc. 103, 1242, 1913.
(35) W. Haworth and A. Fyfe, J. Chem. Soc. 105, 1659, 1914.
(36) W. Haworth and W. Perkin, Jr., J. Chem. Soc. 93, 573, 1908.
(37) W. Haworth and W. Perkin, Jr., J. Chem. Soc. 103, 2225, 1913.
(38) W. Haworth, W. Perkin, Jr., and O. Wallach, Ann. 379, 131, 1911.
(3Q) G. Henderson and T. Smeaton, J. Chem. Soc. 117, 144, 1920.
(40) T. Henry and H. Paget, J. Chem. Soc. 1931, 25.
(41) D. Hibbit, R. Linstead, and A. Millidge, J. Chem. Soc. 1936, 476.
(42) J. Hosking and W. Short, Rec. trav. chim. 47, 834, 1928.
(43) I. Jegorowa, J. Russ. Phys. Chem. Soc. 43, 1116, 1911.
(44) F. Kay and W. Perkin, Jr., J. Chem. Soc. 87, 1066, 1905.
(45) F. Kay and W. Perkin, Jr., J. Chem. Soc. 89, 839, 1906.
(46) K. Kafuku, T. Nozoe, and C. Hata, Bull. Chem. Soc. Japan 6, 40, 1931.
(47) N. Kishner, J. Russ. Phys. Chem. Soc. 43, 1398, 1911.
(48) E. Knoevenagel and R. Schwartz, Ber. 39, 3441, 1906.
(49) E. Kremers, Am. Chem. J. 17, 692, 1895.
(50) R. Kuhn and M. Hofifer, Ber. 67, 357, 1934.
(51) S. Lebedev, J. Russ. Phys. Chem. Soc. 45, 1296, 1913.
(52) S. Lebedev and S. Sergjenko, Compt. rend. (U.S.S.R.) 1935, II, 78.
(53) S. Lebedev and N. Skawronskaja, J. Russ. Phys. Chem. Soc. 43, 1136, 1911.
(54) R. Levina and D. Trakhtenberg, J. Gen. Chem. (U.S.S.R.) 6, 764, 1936.
(55) R. Linstead, A. Wang, J. Williams, and K. Errington, J. Chem. Soc. 1937, 1136.
(56) B. Luff and W. Perkin, Jr., J. Chem. Soc. 97, 2154, 1910.
(57) B. Luff and W. Perkin, Jr., J. Chem. Soc. 99, 518, 1911.
(58) B. Mereshkowsky, J. Russ. Phys. Chem. Soc. 45, 1940, 1913.
(59) R. Padmanabhan and K. Jatkar, J. Am. Chem. Soc. 57, 334, 1935.
(60) W. Perkin, Sr., J. Chem. Soc. 81, 292, 1902.
(61) W. Perkin, Jr., J. Chem. Soc. 97, 2129, 1910.
(62) W. Perkin, Jr., J. Chem. Soc. 99, 727, 1911.
(63) W. Perkin, Jr., J. Chem. Soc. 99, 741, 1911.
(64) W. Perkin, Jr. and K. Matsubara, J. Chem. Soc. 87, 661, 1905.
(65) W. Perkin, Jr. and G. Tattersall, J. Chem. Soc. 87, 1083, 1905.
(66) W. Perkin, Jr. and G. Tattersall, J. Chem. Soc. 91, 480, 1907.
(67) W. Perkin, Jr. and J. Thorpe, J. Chem. Soc. 89, 795, 1906.
(68) W. Perkin, Jr. and O. Wallach, Ann, 374, 198, 1910.
(69) L. Pesci, Gazz. chim. ital. 16, 225, 1886.
(70) G. Pigulevsky, E. Kanetskaya, and M. Platonova, J. Gen. Chem. (U.S.S.R.) 7, 873, 1937.
(71) J. Read and A. Watters, J. Chem. Soc. 1929, 2165.
(72) A. Richard, Compt. rend. 153, 116, 1911.
(73) F. Richter and W. Wolff, Ber. 63, 1721, 1930.
(74) H. Rupe and F. Emmerich, Ber. 41, 1393, 1908.
(75) H. Rupe and F. Emmerich, Ber. 41, 1750, 1908.
(76) L. Ruzicka and A. van Veen, Ann. 468, 133, 1929.
(77) M. Saijew, J. Russ. Phys. Chem. Soc. 44, 1023, 1911.
(78) M. Saijew, J. Russ. Phys. Chem. Soc. 47, 2128, 1915.
(79) R. Schiff, Ann. 220, 71, 1883.
(80) F. W. Semmler, Ber. 39, 4424, 1906.
(81) F. W. Semmler and A. Becker, Ber. 46, 1814, 1913.
(82) F. W. Semmler and C. Rimpel, Ber. 39, 2582, 1906.
(83) F. W. Semmler and E. Schossberger, Ber. 42, 4644, 1909.
(84) F. Tiemann and R. Schmidt, Ber. 29, 694, 1896.
(85) J. Timmermans, Bull. soc. chim. Belg. 27, 334, 1913.
(86) W. Treibs and R. Schmidt, Ber. 61, 459, 1928.
(87) L. Tschugajew, J. Russ. Phys. Chem. Soc. 36, 993, 1904.
(88) L. Tschugajew and Pokrowski, J. Russ. Phys. Chem. Soc. 39, 1338, 1907.
(89) S. Uchida, J. Am. Chem. Soc. 38, 687, 1916.
(90) E. Urion, Ann. chim. [11] 1, 5, 1934.
' (91) 0. Wallach, Ann. 227, 277, 1885.
(92) O. Wallach, Ann. 230, 225, 1885.
(93) O. Wallach, Ann. 239, 27, 1887.
(94) 0. Wallach, Ann. 245, 191, 1888.
(95) 0. Wallach, Ann. 246, 221, 1888.
(96) O. Wallach, Ann. 357, 49, 1907.
(97) O. Wallach, Ann. 362, 285, 1908.
(98) 0. Wallach, Ann. 368, 1, 1909.
(99) O. Wallach and E. Conrady, Ann. 252, 141, 1889.
(100) O. Wallach and O. Rahn, Ann. 324, 79, 1902.
397
3. CYCLENES WITH TWO ALKENYL OR ONE ALKADIENYL
SUBSTITUTIONS, C.H*,., " C,,H,,
Name and Carbon Skeleton
\/r n o/-
M. Jr., C.
B. P., C.
@ 760mm
D?
-s
Additional Data
l,5-Dimethyl-3-(2-
methylpropen-2-yli-
dene)-cyclohexene-l
c
103 to 106
0.8619 >
1.52159
1
@ 17mm
@22.2
@22.3
A
1.51543
c c-oc
1
1.53781 >
1
c
H ft
1. 55360 J
n ri
y
l,3,3-Trimethyl-2-,
butadienyleyclo-
hexene-x
108 to 110
0.8784
1.5320 fl
@ 15mm
2,4,4-Trimethyl-
3-butadien-x,Jt-yl-
cyclohexene-x
96 to 97
0.8675
1.5000 8
@ 16.5mm
398
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D
w />
Additional Data
l-Methyl-4-(l,5-di-
methylhexadien-2,4-
M=-64.0'-
yl)-cyclohexene-l
f_,l 77 2Q 18
[<*j /5.5O **
(Zingiberene)
160 to 161 13
0.8638 8
1.4870
[)=- 60 '
@ 327mm
D*
@30
C
137 to 139 10
0.8684 14
1. 49399 "
|a| I) =-.S9.5"
@ 17mm
0.8731 13
1.4956"
128 to 130 "
0.874 ll
1.4975
C
@ 12mm
@17
1.4984"
1 1
c-e-oc-c=c-c
128 to 129 14
@9mm
0.8733 10
@16
1.49041 13
119 to 123 8
W 20
@ 3mm
7/
1.50319"
1.51112"
nf {
l-Methyl-4-(l,5-di-
methylhexene-4-
ylidene)-cyclo-
hexene-1
(Bisabolene)
262 to 263
0.8717"
1.4923 "
@ 756mm
@21
@ 21
C
261 to 262 l *
0.873 '
1.4901 6
@ 752mm
0.8798 w
1.4935 1
261 to 262 8
0.873 *
1.4910 8
II
@ 751mm
@15
19.5
II
oc-c-oc=c-c
1
133 to 134 15
@ 12mm
0.8759 5
c
131 *
399
Name and Carbon Skeleton
M. P. t C
B. P., c.
<"'< 760mm
D?
ng
Additional Data
M-Isopropenyl-l-(4-
methylpenten-3-yl)-
[ a \ D - 10.59 *
cyclohexene-1
(Cycloisopropenemyrcene)
242 to 244 4
0.8817
1.4915 4
136 to 139
@19
1.4993
C-C-OC-C
1 1
@ 14mm
0.905 *
@19
o
136 @ llmm 4
1
c
c c
CieH.20
3-Methyl-5-(2,6-di-
methylheptadien-x,*-
yl)-cyclohexene-l
143 to 144 7
0.923 7
1.4988'
@ 15mm
@ 18.5
18.5
\
0.920 T
1.5040 7
c-c-o-c-c-c-c c
1 1
@ 16.5
@ 16.5
c c
(1) K. v. Auwers and G. Peters, Ber. 43, 3094, 1910.
(2) Burgess and Co., Oct. 1909, 24.
(3) H. Burgess and T. Page, J. Chem. Soc. 85, 414, 1904.
(4) H. Dieterle and P. H. Kaiser, Arch. Pharm. 270, 413, 1932.
(5) E. Gildemeister, and W. Muller through O. Waliach, "Festschrift," p. 414.
(6) J. Kandel, Compt. rend. 205, 994, 1937.
(7) E. Knoevenagel, J. prakt. Chem. [2] 97, 288, 1918.
(8) K. Moudgill, J. Indian Chem. Soc. 5, 251, 1928.
(9) L. Ruzicka and W. Bosch, Helv. Chim. Acta 14, 1336, 1931.
(10) L, Ruzicka, J. Meyer, and M. Mingazzini, Helv. Chim. Acta 5, 345, 1922.
(11) L. Ruzicka and A. G. van Veen, Ann. 468, 143, 1929.
(12) Schimmel and Co., Oct. 1909.
(13) O. Schreiner and R. Kremers, Pharm. Arch. 4, 141, 1901.
(14) P. W. Semmler and A. Becker, Ber. 46, 1814, 1913.
(15) J. L. Simonsen, "The Terpenes," Vol. 2, p. 493, London, Cambridge University Press, 1932.
400
4. CYCLENES WITH AN ALKENE-ALKYNE OR ALKATRIENE
C,,H SUBSTITUTION, C.H*
Name and Carbon Skeleton
M. F.,C.
B. P., C.
@ 760mm
Of
-8
Additional Data
l-(3-Propylhexen-3~
yne-l)-cyclohexene-l
oc-c
1
csooc-c-c
98 to 100 *
@ 2mm
0.8796 s
1.5160 2
2,4,4-Trimethyl-3-(3-
methylhexatrien-
1 ,3,5-yl)-cyclohexene-l
c
(^\ /
127 to 130 '
@ 10mm
/\ oc-oc~c=c
c c |
c
Ci7 XI 28
l-(3-Butylhepten-3-
yne-l)-cyclohexene-l
c-c-c-c
1
csc~c=c-c-c-c
6
112 to 113
@2mm
0.8724
1.5110 1
(1) P. Karrer, H. Salomon, R. Morf, and O. Walker, Hetv. Chim. Acta 15, 878, 1932.
(2) G. A. Nesty and C. S. Marvel, J. Am. Chem. Soc. S9, 2662, 1937.
IX. CYCLODIENES OR CYCLODIOLEFINS
1. Cyclodienes with alkyl substitutions, C n H 2rt _
2. Cyclodienes with an alkenyl or olefin substitution, C n H tu _ 6
403
1. CYCLODIENES OR CYCLODTOLEFINS WITH ALKYL
SUBSTITUTIONS, C,,H,,, <
C 6 H
Name and Carbon Skeleton
M. J>.t\
n. r., c.
(f^ 760mm
,r
"2
Addithuttil Duid
Cyclopentadiene
- 85 8 '
42.5 2
0.803 28
1.4398
40 8i
0.7983 no
@ 19.5
41 *
@19,5
1.4446"
41.5 to 42
0.80475 *
@ 18.6
41 110
@ 18.6
1. 44627 4
@ 757mm
0.8070 4
@ 16.1
40.2 to 41.6 4
@i6.r
1. 44632 4
@ 757mm
0.8085 4
@ 16.1
40.2 to 40.8 4
@16.1
1.44113 82
@ 757mm
0.8071 87
""*
40 to 41 S4
15.7
1. 44252 4
@ 755mm
0.81500 6fl
H H ml
40 83
@ 715mm
0.8083 27
1.443 78 27
1.44443 27
n 1 *- 1
a
1. 45380
"//
1.45533 4
n it'
ft
1. 45662 27
1. 457332 s7
1.46318 4
"A"
y
1. 46353 4
JJ-
y
1. 46462 27
n H >
y
1.46539"
H ' 4< ^
y
C,H,
404
Name and Carbon Skeleton
M. 7\ t C.
ft. P., C.
('A 760mm
iff
115
Additional Data
x-Methylcyclopenta-
diene-x,jt
69 to 70 "
0.8200 "
1.4460"
@ 736mm
,,r
18
l-Methyl-3-ethyl-
cyclopentadiene-1 ,3
c
135
-O
c-c
l-Methyl-3-isopropyl-
cyclopentadiene-1 ,3
c
152 to 158 8&
0.840 86
1.47S8"
50 to 55 86
@ 20mm
c-c
1
1
c
405
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
U D
Additional Data
3-Methyl- 1-isopropyl-
cyclopentadiene-1 ,3
c-c-c
147 to 149 84
0.825 "
1.4630 84
cS
@15
@1S
~~\
c
3-Methyl-l-isopropyl-
cyclopentadiene-1 ,3-
or
3-Methylene-l-iso-
propyl-cyclopentene-1
c~c~c c-c-c
1 I
166 to 167 9
0.845 86
1.4913 96
~~\ \
c c
1 ,5-Dimethyl-4-iso-
propylcyclopenta-
diene-1,3
H,~l.9-
(Isothujene)
(Tanacetene)
C
vS
172 to 175 90
171 to 178 55
171 to 176 54
170 to 172 91
60 to 63 74
@ 14mm
0.8386 65
@22
0.836 91
0.840 "
0.8408 74
0.8400 84
1.47145 91
1.4761 90
1.476 74
1. 47674 56
1.4789 54
w
@17
c-c
1
c
C,H,
406
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
-B
Additional Data
Cyclohexadiene- 1 ,3
.^
81.5
0.8296 21
1.4679 82
j 1
81 to 82 .*
#5J
22
\^
81 19
0.8347
1.4742 17
80.5 to 81
@22
1.4699"
80.13 17
0.840
1.4755"
80 to 81 l06
0.8410
1.4628 108
80 30
0.8413 "
@ 18.5
79.8 to 80 m
0.8451 1W
1.4788 m
/^> < QO
80.5 to 80.7 101
0.8478 16
(fy -I O
@ 752mm
0.8503 39
1.4760 30
@ 16
83 to 84 *
@ 750mm
D\l
0.8340 l08
1.4766 104
@ 16
79 to 80 62
@18.5
@ 750mm
0.8421 30
1. 47254 83
79 to 80 1M
16
H
@ 736mm
0.8489 104
1.46371 21
16
w //' 4
0.84785 33
1. 48687 33
@15.5
^ J
0.83659 2 '
ft
@15.4
1.47672"
^15.4
0.8377 21
^fl
D\l
1.49589"
0.84987 83
D 15
1. 48493
0.8454 w
n)J- 4
@10
7
0.8476 21
@4
407
C,H,
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
iff
-8
Additional Data
Cyclohexadiene-1 ,4
88.4 to 89.4 1<M
0.8357
1.46806"
769mm
Dn
25
85.5 l06
0.8569 IW
1.4679 l11
85 to 87 m
0.8471
! 4729 100
84 to 86 "
0.8519 1M
1.4781 *
86 to 87 7
@15
15.2
@ 750mm
0.8605 78
78 to 79 i"
@10
@ 750mm
Cyclohexadiene-x,*
* Index of refraction
82 to 83 3l
0.8466 16
1.47296"
for other wave
82 to 84 18
21.2
21.2
lengths given by
@ 718mm
0.846 31
1.46921 16
author. l
0.8478 16
w lr' 2
1.48258"
n S*
1. 49092 "*
ng- 2
C 7 H 10
2-Methylcyclo-
hexadiene-1,3
c
110 106
@ 741mm
fioe,
0.8292( 107
fioe,
1.4710( 1W
408
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
X
-8
Additional Data
d-5-Methylcyclo-
hexadiene-1,3
X^
105.5 to
0.8274 106
1.4680 105
1 j
106 105
c
5-Methylcyclohexa-
diene-1,3
100.5 to
0.8252 3 8
1.46619 3 8
101. 5 38
@ 22.5
@ 22.5
@ 762mm
1.46225"
1.48519"
y
jc-Methylcyclohexa-
diene-1,3
108 to 110 66
0.7970 8S
1.4444"
106 to 107 M
0.8014 53
1.4460"
@ 18.3
@ 18.3
0.8088 M
409
CS.HU
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
Iff
s
Additional Data
1 ,3-Dimethylcyclo-
hexadiene-1,3
(Dihydro-w-xylene)
135 to 137 65
0.8324 a
1.441 87
135 to 136 43
0.8373
@23
C
133 to 135 3
0.8389
1.4697 65
133 to 134 3
0.8270 8
1.4787"
132 to 135 3
@17.6
1.4856 43
\
131 w
0.8356 s
1.46621 8
C
@ 16.6
@17.3
0.8365 8
1.47368 s
16.2
@ 16.6
1.47388 s
@16.2
1.46621 s
a
1. 46959 s
n ff '
a
1.46994 s
1. 47934
1.48249 s
,,16.6
e
1. 48287 3
1. 48646 s
v
1. 49053 3
1. 49180 3
7
410
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
Of
s
Additional Data
1 ,4-Dimethylcyclo-
hexadiene-1,3
c
135 to 138
0.8306 6
1.4792 1 70
1
29.7 to 30 70
@ 19
1.47966*
o
@13mm
29.5 to 29.9
0.8358 70
@ 16.3
@19
1. 49380
c
@ llmm
0.8366
@15.5
1. 49385 6
1.47535 5
a
1. 47554 70
W 16.3
a
1. 48219*
n lB ' 1
1.47793*
a
1.49129 6
H H
1. 49079 70
1. 49380 .
1. 49385
1.50191 6
W5J ,
1. 50074 70
1.50459*
7
1. 50445 8
W 15.7
'r
411
Name and Carbon Skeleton
M. P.,6
B. P., C.
@ 760mm
Iff
S
Additional Data
1 ,5-Dimethylcyclo-
hexadiene-1,3
c
128 to 130 3
128 to 129 7
0.821 7
0.8229 '
1.471'
1.47212 7
124 to 126 7
19.8
@19.7
,
c
@ 756mm
130 to 132.3 7
0.8189 7
@19.7
1.46877'
@19.5
@ 754mm
0.8205 '
1.46946'
128 to 130 7
@ 18.4
@ 18.9
@ 754mm
0.8221 7
1.47103'
126.8 to 128 7
@18
@18.7
@ 754mm
0.8203 3fl
1. 46360
126 to 128 85
pj;
@ 18
@ 750rnm
0.8272
1.47466'
@16.2
@ 16.0
1.467'
*
1. 46828 7
a
1.46493 '
n*
1.46561 7
1.46719'
^18.7
n /f
a
1.47052'
W U'
a
1.48214'
1.47850
ng-*
1.47939 '
1.48096'
wg- 7
1.48476'
1.49096'
n"- 7
412
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
D?
-s
Additional Data
1 ,5-Dimethylcyclo-
hexadiene-1,3
(Continued)
1.48725 7
^19.6
X
1.48821 7
n%*
1.48978 7
1. 49367 7
2 ,3-Dime thylcyclo-
hexadiene-1,3
c
135.5 43
0.8521 43
1.4895
c
2,3 or 5,6-Dimethyl-
cyclohexadiene- 1 ,3
(Karanthrene)
138 to 139"
0.8373 89
1.4692 69
C C
I 1 or 1
c c
135.5
134 to 137 89
134 to 135
134 3
0.8521
0.8531 72
@ 18.6
1.4895 43
1.491 18 39
1.4848 72
@ 18.6
1.4966 39
@18
413
Nat tut and Cur bo it Skeleton
Af. /VC.
B. P., C.
(m 760mm
I)?
"S
Additional Data
2,5-Dimethylcyclo-
hexadiene-1,3
c
132.5 to
133.5 l06 ' 107
0.8223J 1 ;;
fl06,
1.467S{ |W
1 1
131.5 to
/^^
132.5 l M 7
c
@ 740mm
2 ,6-Dimethylcyclo-
(a\ D = 27.38 '
hexadiene-1,3
c c
129 to 130 106
0.8225 m
1.4675 100
^s^
@ 745mm
0.8268 m
5 ,5-Dimethylcy clo-
0.810 3
^
hexadiene-1,3
d/ (5 to 25)
r^
111 20
0.8083
1. 45630 39
\r i
@ 770mm
D 2B
@ 18
c
110 to 111 39
0.8117
1. 45482 61
0.814
1.46733
Dl!
n'}
/7 /J
0.8153 61
1.47530"
0.81573
*
@14
0.8193
D 10
0.8246
4
414
Name and Carbon Skeleton
M. P.fC.
B. P., C.
(& 760mm
*
S
Additional Data
1 ,4-Dimethylcyclo-
hexadiene-1,4
c
$
c
133 to 134
@ 720mm
3 ,3-Dime thylcyclo-
hexadiene-1,4
a c
0.8421
1.47691 38
0.8433
c
Z>5!
1,3-Dimethylcyclo-
hexadiene-x,*
133 to 134
0.8275
1.4675 w
132 to 134"
x,x-Dimethylcyclo-
hexadiene-x,x
123 M
0.7948
1.4416 M
@ 20.5
20.5
0.7998 "
415
Nante and Carbon Skeleton
Af. P.,C.
B. P. t C.
@ 760mm
D?
5
Additional Data
5-Isopropylcyclo-
hexadiene-1,3
f^i
165 to 167 M
0.846 M
1.495 84
/v^
C' ('
1
I
c
1-Isopropylcyclo-
hexadiene-x,*
c-c-c
6
140"
0.8142"
1.4628 77
1 -Methyl-4-ethylcyclo-
hexadiene-1,3
c
160.9 to
0.8371 *
1. 48413 70
161.2*
@ 19.5
1.48250*
@ 761mm
0.8408 2
1.48181*
159.5 to
@ 18.8
@ 19.9
1
c-c
160
@ 751mm
0.8393 2
@ 18.4
1.49263 *
@18
51 to 51.2 70
@ 14mm
0.8408 70
@ 15.6
1.47828*
46 70
@12mm
0.841 1
@ 15.2
1.477 S 50*
1.47823 *
-B.
1.48002
a
1.49353 *
416
Name and Carbon Skeleton,
M. /Vc 1 .
B. P., *C.
fy 760mni
"
,,.
Additional Data
l-Methyi-4-ethylcyclo-
hexadiene-1,3
(Continued]
1 .49294 2
1.49345 2
1.49537 ro
1.50422 2
w ^/
Y
1.5037 1 2
7
1.50347 2
1. 50574 70
1 ,3,5-Trimethylcyclo-
hexadiene-Jt,JC
(Dihydromesitylene)
166 to 168
0.8454 85
1.4773 6
147 9a
0.8475 ' 5
1.4810 w
C
0.826 w
o c
417
Name and Carbon Skeleton
M. F.,C
B, P., C\
(to 7 60mm
*
M 50
"It
Additional Data
1 -Methyl-4-propy 1-
cyclohexadiene-1 ,3
c
65.4to66 70
0.8353 70
1. 47942 70
1
13.5mm
0.8713 98
@18.9
62 to 72 98
@ 15
1.48761
6mm
0.8726 98
@ 15
1
Df
1.47535 70
e-c-c
n;
1.49013'
"'B
1. 49979 70
n u'
l-Methyl-4-isopropyl-
cyclohexadiene-1 ,3
(a-Terpinene)
174 to 176 3
0.8441 36
1.48451 36
766mm
D 27
27
C
163 to 166 64
0.8529 25
1.4748
1
765mm
D"
23
179 to 181 94
0.8443 79
1. 49065 79
179 to 1 80.5 8
20.2
20.2
C-C-C
174.8 to
0.834 7fi
1.4784 78
175.2 78
0.845 70 - 76
1.4789 94
173.5 to 175
0.846 94
1.480 84
755mm
0.8361 z
1 .4905 75 - 76
173.5 to
19.6
1.477 67 ' 69
174.8 69
0.8375 9
19.7
@ 755mm
19.6
1.47810 ^
174.8 to
0.8353 70
19.4
175.4
18.9
1.47942 70
@ 750mm
0.841 1 39
18.9
160 to 164 fl4
@ 750mm
0.8423 39
1. 48724 42
18.5
174 to 176 >
@ 742mm
D 18 ' 6
0.8474 42
1. 48579 41
18
68 to 70 41
T^18.5
1. 48005 '
@ 15mm
^ 5
62@15mm fi7
0.8382
@ 16.9
@ 18.3
io Hie
418
Name and Carbon Skeleton
If T> /~*
kZ. / ., \s>
B. P., C.
@ 760mm
..*
8
Additional Data
l-Methyl-4-isopropyi-
cyclohexadiene-1 ,3
(Continued)
65. 4 to 66
0.838
1.48107 >
13.5mm
18
16.6
60 to 63 4Z
0.8453
1.48015 l
@12mm
18
15,8
59 to 62
0.8361
1.48722 2
@ 10mm
16.2
14.8
59 to 60
0.8372
1.48218
11,5mm
16
13
61. 5 to 62. 5"
0.8389
1.48822 s
10mm
16
12,5
0.8408
1. 49070 2
16
12.5
0.847 *
1.48643"
16
M 20.2
X
0.8504 2
1. 47359 >
16
n W.4
0.8538 2
12.9
1.47535 J
0.8561 2
tf .
12.1
1.48333 >
1.47535
a
1. 47637 >
wjj- 6
a
1.47603
n^
1.48273 s
1.47807
1.48393 s
jv
1.48655 J
1.50169
1.48837
419
Name and Carbon Skeleton
Kf r* r*
t\i , I . , L
B. P., C.
(a) 76()rmn
D<
"j>
Additional Data
l-Methyl-4-isopropyl-
cyclohexadiene-1 ,3
(Continued)
1. 49013
H
1. 49022
1. 49707 2
^14.8
1. 49286
w)J
1. 49828 *
n 13 * 6
7
1. 50087 2
7,12.6
1.51 166 7
W 20.2
7
1.49795
7
1. 49979
^18.9
7
1.50701 l
?| 18.6
7
1. 50006 *
7
1. 50064 l
7
1.50018 l
r ,15.8
*7
1.50631 '
7
1.50254
n a ^
1.50744*
n !2.6
7
1.51031 *
H
420
Name and Carbon Skeleton
M. P.,C.
n. p., c.
(" 760mm
iff
?,
Additional Data
1 -Methyl-5-isopropyl-
cyclohexadiene-1 ,3
c
169 to 171 47
0.8515"
1. 47270
1
D 20
c-c
1
1
c
2-Methyl-5-isopropyl-
cyclohexadiene-1 ,3
,] ir -f 44.66 ss
(d-a-Phellandrene)
175 to
0.8324 18
1.4695 18
176 72 - 74
30
30
^=-0.0023/C.
C
172 to 173.5 18
0.8473 40
1. 48825 40
dt (15 to 25)
O /
89.3 to 90.8 18
21
21
56.5mm
0.844 86
1. 48345 40
c~c
70 40
0.8447 40
1 .4732 97
1
15mm
0.8440 97
19
c
66 40
19
14mm
0.8565 7 <
61 97
15
llmm
421
Name and Carbon Skeleton
M. P.C.
B. P., C.
760mm
Of
5
2-Methyl-5-isopropyl-
cyclohexadiene-1 ,3
(/-a- Phellandrene)
174 to 177 *
0.8459
1.466
759mm
30
30
171 to 172 80
0.8372 80
1.4725 80
758.2mm
25
25
173 to 175 G0
0.8387 80
1. 47697 6
@ 758mm
25
22
173 to 175 67
0.8426 5
1.4732 80
754mm
22
1 .488 92
67 to 68 *
0.8410
19
22mm
0.8425 80
1.4737 6t)
65.2 to 66 M
0.8465 92
17.5
@ 17mm
19
1. 47746 5
64 to 66 "
0.8490 5
17.1
17mm
17.1
1.48014 57
58 to 59 80
0.844 67
17
@ 16mm
15
1.47328 5
60 to 60.5 67 > 69
0.8448 67
".
15mm
15
1.4741 8
65 92
17 1
12mm
"''a
1. 48624 5
1. 48580 5
1. 49447 5
1. 49287 5
V
t#-a-Phellandrene
175 to 176 5
0.841 6
1.4760 96
22
22
Additional Data
l=- 112.76
=- 18.37 60
422
Name and Carbon Skeleton
M. P.C.
B. P., C.
@ 760mm
ti?
*
Additional Data
1 -Methyl-4-isopropyl-
cyclohexadiene-1 ,4
W.-+2.S-
(y-Terpinene, Moslene)
183 87 -
0.849 7 - M
1.4783 1M
C
179 to 181 "
0.846 61
0.8515 M
@21
1.4789"
178.5 to
D\l
1.4779"
1
c-c-c
180.5
@ 740mm
174 10
69 to 73 M
0.853
1.4785
1.4754 71
@ 15.6
@ 20mm
1.4765 87 - 69
72.5 7 '"
@ 14.5
@ 18mm
1.4720 71
65.5 to 68 l09
W 15.6
@ 14mm
1.4827 71
wJJ- 6
1.4894 71
W 15.6
>
Methyl-isopropyl-
cyclohexadiene
171 to 172 63
0.81 70 63
i.4564 53
1,3-Diethylcyclo-
hexadiene-1,3
c-c
1
68. 9mm 14
c-c
423
Vaw* and Carbon Skeleton
M.PSC.
J3 p O/"
D. Jr., C.
@ 760mm
DT
w' 2(i
Additional Data
1 ,5-Diethylcyclo-
hexadiene-1,3
c-c
166 to 168
0.8659
1. 47575
1
D 20
c-c
1,2-Diethylcyclo-
hexadiene-x,*
60 to 63 74
0.8408 74
1.476 74
@ 14mm
1 ,2 ,3 ,4-Tetramethyl-
cyclohexadiene-1 ,3
c
180 to 182
0.8482
1.4816 6
i .
0.8516 66
1.4850 85
i \
c
424
Name and Carbon Skeleton
M. P.,C.
B. P. t C.
(& 760mm
D?
*
Additional Data
l-Methyl-4-isopropyl-
cyclohexadiene-x,*
WS-+MT-
173.5 < 4
0.8272
1.464
172tol74 4fl -"
0.8337
1.46430"
75 to 80 13
0.8491 13
1. 46539"
@ 9mm
0.8408 60
1.49824"
D 20
0.8540 B0
CTT
It J-ll8
1 ,3-Dimethyl-4-iso-
[a]^=+0.04
propylcyclo-
hexadiene-1,3
c
184 to 186 ea
0.8585 8
1.484S M
rS
@ 737mm
(S)25
@25
\^
c-c-c c
C,,H M
l-Methyl-3-ethyl-4-
[]!= 4-0.07 66
isopropylcyclo-
hexadiene-1,3
c
199 to 202 6
0.8631 66
1.4854"
@ 737mm
@25
25
83 to 85 66
\
@ 15mm
1 c-c
c-c-c
425
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
DT
H D
Additional Data
1 -Methyl-3-propyl-4-
isopropylcyclo-
hexadiene-1,3
c
104 to 106 M
0.8872
1.4865 66
1
14mm
@25
@25
1 c-c-c
c-c-c
Cycloheptadiene-1 ,2
118 to 119 32
0.8532 M
Cycloheptadiene-1 ,3
* Index of refraction
values for other
120 to 121 58
0.8679 2y
1. 50066 28
wave lengths given
120 to 121 101
@ 17.6
U K
by ref. (29).
@ 724mm
0.8859 28
1.51663 28
118 to 119 101
@ 12.4
@ 720mm
118 to 119 9
{100,
,01
1.49597 29
@ 7 15mm
<5>0
w //' tt
0.8815 101
1.51202 2
,,17.0
11 8
0.8823 10
0.8929
426
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
g
Additional Data
2,6,6-Trimethylcyclo-
heptadiene-1,4
(Euterpene)
161 to 165
C
c >o x
c
Cyclo5ctadiene-l,3
39.5 102
0.884 "3
@ 16.5mm
Cyclooctadiene-1 ,4
or -1,5
/^ A^\
143 to 144 IM
0.887 103
U-'O
Cyclooctadiene-1,5
/^^\
50 to 52
0.8564
1. 49646 M
@ 17mm
@ 20.7
@ 20.7
427
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
or
n-
Additional Data
3,4-Dimethylcyclo-
octadiene-1,5
68 to 71
0.8623 * 2
1. 49036 22
c
@ 15mm
@13
@13
\
c
-30-H.56
Cyclotriacontadiene-
1,16 or -1,15
^ C K ^ C W
50 to
240 73
0.8218 73
1.4564 78
II II or II ||
c Jp c c
52 73
@ 0.4mm
80
2a-> Hco
1 , 1 6-Dimethylcyclo-
triacontadiene-1,16 or
*Several values for
He listed"
-1,15
x^K /C C x ^C^ 4 /C
64 to
250 @ 1mm 73
0.8302 73
1.4641 73
c ' c c 4 c
65"
@80
@80
c c or c c
428
(1) K. v. Auwers and F. v. Heyden, Ber. 42, 2404, 1909.
(2) K. v. Auwers, Ber. 42, 2424, 1909.
(3) K. v. Auwers and P. Eisenlohr, Ber. 43, 827, 1910.
(4) K. v. Auwers and F. Eisenlohr, Ber. 43, 806, 1910.
(5) K. v. Auwers and F. Eisenlohr, J. prakt. Chem. [2] 82, 65, 1910.
(6) K, v. Auwers and R. Hinterseber, Ber. 48, 1357, 1915.
(7) K. v, Auwers and G. Peters, Ber. 43, 3111, 1910.
(8) K. v. Auwers, W. Roth, and F. Eisenlohr, Ann. 373, 267, 1910.
(9) A. Baeyer, Ber. 25, 2122, 1892.
(10) A. Baeyer, Ber. 26, 232, 1893.
(11) A. Baeyer, Ann. 278, 88, 1894.
(12) A. Baeyer and V. Villiger, Ber. 31, 2067, 1898.
(13) A. Berkenheim. Ber. 25, 686, 1892.
(14) E. E. Blaise and M. Moire, Bull. soc. chim. [4] 3, 13, 1909.
(15) J. Briihl, Ber. 17, 1065, 1894.
(16) J. Briihl, J. prakt. Chem. [2| 49, 201, 1894.
(17) E. P. Carr and H. Stucklen, J. Chem. Phys. 6, 55, 1938.
(18) A/Clover, Am. Chem. J. 39, 613, 1908.
(19) R. Cricgee, Ann, 481, 263, 1930.
(20) A. Crossley and H. Le Sueur, J. Chem. Soc. 81, 821, 1902.
(21) A. Crossley, J. Chem. Soc. 85, 1404, 1904.
(22) O. Doebner, Ber. 35, 2129, 1902.
(23) R. Duden and R. Freydag, Ber. 36, 944, 1903.
(24) F. Ebel, R. Brunner, and P. Mangelli, Helv. Chim. Acta 12, 19, 1929.
(25) L. Elson, C. Gibson, and J. Simonsen, J. Chem. Soc. 1929, 2732.
(26) A. Etard and P. Lambert, Compt. rend. 112, 945, 1891.
(27) J. P. Eykman, Chem. Weekblad 4, 41, 1907. *
(28) J. F. Eykman, quoted by R. Willstatter, Ber. 31, 1534, 1898.
(29) J. F. Eykman, quoted by R. Willstatter, Ann. 317, 232, 1910.
(30) E. Farmer and W. Scott, J. Chem. Soc. 1929, 172.
(31) W. Faragher, W. Gruse and F. Garner, Ind. Eng. Chem. 13, 1044, 1921.
(32) A, Favorsky, J. Gen. Chem. (U.S.S.R.) 6, 720, 1936.
(33) E. Fortey, J. Chem. Soc. 73, 932, 1898.
(34) D. Hammick and D. Langrish, J. Chem. Soc. 1937, 797.
(35) C, Harries, Ber. 35, 1166, 1902.
(36) C. Harries, Ann. 328, 322, 1903.
(37) C. Harries, Ber. 41, 1698, 1908.
(38) C. Harries and R. Seitz, Ann. 395, 211, 1913.
(39) C. Harries and W. Antoni, Ann. 328, 88, 1903.
(40) C. Harries and M. Johnson, Ber. 38, 1832, 1905.
(41) C. Harries and R. Majema, Ber. 41, 2516, 1908.
(42) C, Harries and G. Morrell, Ann. 410, 71, 1915.
(43) W. Haworth, J. Chem. Soc. 103, 1242, 1913.
(44) W. Haworth, quoted by W. Rudolph, Arch. Pharm. 254, 423, 1916.
(45) G. Henderson and R. Boyd, J. Chem. Soc. 99, 2159, 1911.
(46) G. Henderson and S. Schotz, J. Chem. Soc. 101, 2563, 1912.
(47) G. Henderson and T. Smeaton, J. Chem. Soc. 117, 144, 1920.
(48) G. Henderson and M. Sutherland, J. Chem. Soc. 97, 1619, 1910.
(49) F. Hofmann and P. Damm, Schlesischen Kohlenforschungs inst. d. Kaiser Wilhelm Ges. 2, 97,
1925; Chem. Zentr. 1926, 1, 2342.
(50) R. Horiucki, Mem. Coll. Sci. Kyoto Imp. Univ. Ser. A 11, No. 3, 171, 1928.
(51) K. Kafuku, T. Ikeda, and C. Hata, J. Chem. Soc. Japan, 56, 1186, 1935.
(52) B. Kazansky and L. Volfson, J. Gen. Chem. (U.S.S.R.) 8, 1685, 1938.
429
(5.*) K. Knoevenaj;d f Ann. 297, II.?, 1897.
(54) I. Kondakow and V. Skivor/ow, J. prakt. Chcin. [2| 09, 1176, 1904.
(55) I. Kondakow and V. vSkivorzow, J. Russ. Phys. Chcni. Soc. 42, 497, 1910.
(56) G. Kraemer and A. Spilkcr, Bcr. 29, 552, 1896.
(57) R. Leimbach, quoted by O. Wallach, "Festschrift" Oct. 1909, 502; Chem. Zentr. 1909, II, 1870.
(58) W. Markownikoff, J. Russ. Phys. Chem. Soc. 27, 285, 1895; Ber. 29, Ref. 89, 1896.
(59) H. Meerwein, Ann. 405, 148, 1914.
(60) K. Moudgill and P. Vridhchalam, Perfumery, Essential Oil Record 13, 173, 1922.
(61) W. H. Perkin, ST., quoted by A. Crossley and H. Le Sueur, J. Chem. Soc. 81, 821, 1902.
(62) R. Piccard, Ber. 11, 2122, 1878.
(63) R. Piccard, Ber. 12, 578, 1879.
(64) S. Pickles, J. Chem. Soc. 93, 862, 1908.
(65) A. Pictet and M. Kaiser, Ann. chim. [9] 10, 299, 1918.
(66) J. Read and A. Walters, J. Chem. Soc. 1929, 2165.
(67) F. Richter, Private communication [Beilstein, Suppl. Vol. 5, p. 68].
(68) F. Richter and W. Wolff, Ber. 60, 477, 1927.
(69) F. Richter and W. Wolff, Ber. 63, 1714, 1930.
(70) W. Roth and K. v. Auwers, Ann. 407, 145, 1914.
(71) W. Roth and F. Banse, quoted by F. Richter and W. Wolff, Ber. 63, 714, 1930.
(72) W. Rudolph, Arch, pharm. 254, 423, 1916.
(73) L. Ruzicka and H. Boekenoogen, Helv. Chim. Acta. 14, 1319, 1931.
(74) F. W. Semmler, Ber. 25, 3343, 1892.
(75) F. W. Semmler, Bcr. 42, 522, 1909.
(76) F. W. Semmler, Ber. 42, 4171, 1909.
(77) F. W. Semmler and A. Hoffmann, Ber. 37, 234, 1904.
(78) J. Senderens, Compt. rend. 177, 1183, 1927.
(79) F. Sommer, quoted by F. W. Semmler, Ber. 42, 522, 1909.
(80) H. Smith, E. Hurst, and J. Read, J. Chem. Soc. 123, 1657, 1923.
(81) H. Staudinger, Ber. 59, 3019, 1926.
(82) H. Stobbe and F. Reuss. Ann. 391, 151, 1912.
(83) J. Thiele, Ann. 314, 296, 1900.
(84) W. Treibs, Ber. 66, 610, 1933.
(85) W. Treibs, Ber. 66, 1483, 1933.
(86) W. Treibs and H. Schmidt, Ber. 61, 459, 1928.
(87) A. Verley, Bull. soc. chim. [3] 17, 175, 1897.
(88) W. Walbaum and O. Huthig, J. prakt. Chem. [2] 71, 459, 1905.
(89) O. Wallach, Ann. 258, 319, 1890.
(90) O. Wallach, Ann. 272, 99, 1893.
(91) O. Wallach, Ann. 286, 90, 1895.
(92) O. Wallach, Ann. 287, 371, 1895.
(93) O. Wallach, Ann. 323, 135, 1902.
(94) O. Wallach, Ann. 350, 141, 1906.
(95) O. Wallach, Ann. 359, 265, 1908.
(96) O. Wallach, Ann. 414, 195, 1918.
(97) O. Wallach and E. Beschke, Ann. 336, 9, 1904.
(98) I. Wanin and A. Tschernojarowa, J. Gen. Chem. (U.S.S.R.) 7 (69), 885, 1937.
(99) R. Willstatter, Ber. 30, 721, 1897.
(100) R. WillstHtter, Ber. 34, 129, 1901.
(101) R. WiUstatter, Ann. 317, 231, 1901.
(102) R. Willstatter and H. Veraguth, Ber. 38, 1975, 1905.
(103) R. Willstatter and H. Veraguth, Ber. 40, 957, 1907.
(104) N. D. Zelinsky, J. Denissenko, and M. Eventova, Compt. rend. acad. sci. U.R.S.S. 1935, 1, 313.
(105) N. D. Zelinsky and A. Gorsky, Ber. 41, 2479, 1908.
430
(106) N. D. Zelinsky and A. Gorsky, Ber. 41, 2630, 1908.
(107) N. D. Zelinsky and A. Gorsky, J. Riiss. Phys. Chcm. SCK-. 40, 1397, 1908.
(108) N. D. Zelinsky and K. Kozeshkov, Bcr. 60, 1102, 1927.
(109) N. D. Zelinsky and R. Levina, Ber. 62, 339, 1929.
(110) N. D. Zelinsky and R. Levina, Ber. 66, 477, 1933.
-(Ill) N. D. Zelinsky and G. S. Pawlow, Ber. 66, 1420, 1933.
(112) N. D. Zelinsky and A. Titowa, Ber. 64, 1399, 1931.
431
2. CYCLODIENES WITH AN ALKENYL OR OLEFIN
SUBSTITUTION, C,H,.,
Name and Carbon Skeleton
M. /vc
n. P., v.
% 760mm
tif
,r
Additional Dnlii
5-Isopropylidenecyclo-
pentadiene-1,3
(Dimethylfulvene)
153 to 154 12
0.881 "
1.54740"
@ 717mm
0.8858 12
1.53913 "
C
46"
I
o-c
@ llmm
1.56918"
w ?/
3-Cyclopentadien-2 ,4-
ylidenebutane
(Methylethylfulvene)
185 ca
0.8772
1.53702 s
C-C-C-C
II
87.4 to 87.9*
@ 20.9
0.878 "
@ 20.9
1.5375"
II
62.5 w
0.879 "
1.5377"
o
@ 13mm
1.52988*
27 to 29 "
n u'*
@ 0.08 to
0.15mm
a
1.50325"
-s.
1.50326"
a
1.55856"
1.55857"
n u
432
Name and Carbon Skeleton
M. /'.,"('.
n. P., c.
(</; 760mtn
nf
;/, 20
Additional Data
3-Cyclopentadien-2 ,4-
ylidenepentane
I
(Diethylfulvcne)
96.8 to 97.2 :i
0.8812 2
1.52997 s
@40mm
@ 16.4
^ 16.4
c-c-c-c-c
74.5 to 78.5 l
JL
@ 19mm
o
6-Methylene-3,3-di-
methylcyclohexa-
diene-1,4
c.
38 to 40 <
0.8360 3
1. 50295 8
ac
@ 15mm
@15.8
@15.8
0.8430 3
1.5086'
G
@ 14.95
433
Name and Carbon Skeleton
M. p.,r.
B. P., C.
@ 760tnni
/>r
,*J
Additional Data
3,3-Dimethyl-6-ethyl-
idenecyclohexa-
diene-1,4
c-c
81.5 to 84 4
0.857 4
1.51572 4
^r^^ c
@ 25mm
0.8614 4
15.15
c
71 to 73 *
@ 16mm
@ 15.5
0.8613 4
1.51477 4
@14.7
@ 12.8
1.51072 4
1.50982 *
n \<.i
1.53015 4
w-J*- lfi
1.52946 4
1. 54300 4
015.16
1.54221 4
3-Methylene-l ,6,6-
trimethylcyclohexa-
diene-1,4
c
60 to 65 4
0.8735 4
1.51813 4
\. .X'^Ss.
@ 15mm
@10.7
@10.7
1.51331 4
c L J^
n l0.7
c
1.53213 4
10.7
1.54435 4
434
Name and Carbon Skeleton
\f. P. t C,
B. P., C.
@ 760mm
tif
n%
Additional Data
2,3-Dimethyl-6-iso-
propenylcyclo-
hexadiene-1,3
j- +69.12 '
a]^- 103.49 9
c
978
.8724 8
.5000 8
oo c
746mm
@2i.r
@21.1
to 91.5 J
.8747 9
.50152
2 1mm
.8738 >
.49875 l
9.2 to 89.4 l
@19
@ 19.0
c
@ 18mm
0.8686 l
.50124 >
82 to 83
@ 18.8
@ 18.8
15mm
0.8776 7
.50215 7
75 to 76
15
15
10mm
1. 49596
72 to 73
W /J*
8mm
1.4945 1 1
a
1. 49803 7
1.51100 l
n a'*
1.50888
1.51260 7
B.
1.52071 >
7
1.51785
^18.8
T
1.50124'
ng
7
435
Nante and Carbon Skeleton
M. P.,*C
B. P., C.
(n\ 760nim
Iff
n
Additional Data
3,3-Dimethyl-6-propen-
1-yl-cyclohexadiene-l ,4
o-c=c
83 to 85 4
0.8618 4
1.50633*
^r^^i c
@ 13mm
@15.2
@15.2
^X\
1.50^89*
c
*"
1.51925'
1.52040'
n l&.3
v
l,3,3-Trimethyl-6-
ethenylcyclohexa-
diene-1,4
c
85 to 86 4
0.8844 4
1.51931*
c=c |
\X^s
15mm
@12.7
@12.7
1.51470*
c
1.53230*
1.54371 4
7
C 11
436
Name and Carbon Skeleton
M. P. t C.
B. P., C.
% 760mm
if!
<*
Additional Data
6-Methylene-2,3,3,4-
tetramethylcyclohexa-
diene-1,4
c c
89 to 90 4
0.8765 4
1. 51350 4
Vx^s/
@ 15mm
@23.3
@23.2
L < c
1. 50884 4
^y^ \
HJJ'
1 c
c
1, 52660 4
n a'*
1. 53830 4
*t23.2
6-Methylene- 1 ,3 ,3 ,4-
tetramethylcyclohexa-
diene-1,4
c
77 12mm 4
0.8809 4
1.51687 4
c I
@15.2
@15.2
ill c
1.51235 4
U^xx
w i?' 2
c
1. 53006 4
1.54172 4
44 16 .2
7
437
Name and Carbon Skeleton
if TO or*
JKL jr., C.
B. P., C.
@ 760mm
Iff
H D
Additional Data
2-Methyl-3-ethyl-5-
[a]". +86.19 7 - 8
isopropenylcyclohexa-
diene-1,3
(2-Ethyl-^-menthatriene-
100 to 101 *
0.8859 8
1.5041
2,6,8(9))
13.5mm
18
18
0.8880 '
1. 50847 7
C
15
15
1. 50429 7
n a
c=c c-c
1
1.51920 7
C < ,
Hf *0
1.52763 7
l,3,3,4-Tetramethyl-6-
ethenylcyclohexa-
diene-1,4
c
100 to 103 *
0.8837 4
1.51452*
o-c |
18mm
15.4
15.4
o/
1. 51028
c
1.52702*
rcJJ-*
1.53796*
y
438
Name and Carbon Skeleton
\f p o/-
1YJL. 4 , U.
J3. P., C.
@ 760mm
Df
Additional Data
2-Methyl-3-propyl-5-
isopropenylcyclohexa-
diene-1,3
[]-+ 86.20'
(2-Propylmcntha-
triene-2,6,8(9))
107 to 108 7
@ 13mm
0.8804 7
15
1.50273 7
@1S
C
1,49900'
r^
1.51312'
c=c oc-c
1
1.52141'
c
*
2-Methyl-5-isopro-
penyl-3-(3-methyl-
butyl)-cyclohexadiene-
1,3
Tir
c
135 to 137 10
0.8679 "
1.49478"
O/
@ 15mm
0.8703 10
1.4952 10
130 to 132 "
c=c c-c-c-c
1 1
c c
@ llmm
(1) K. v. Auwers and F. Eisenlohr, Ber. 43, 827, 1910.
(2) K. v. Auwers and F. Eisenlohr, J. prakt. Chem. [2] 84, 1, 1911.
(3) K. v. Auwers and K. Muller, Ber, 44, 1595, 1911.
(4) K. v. Auwers and K. Ziegter, Ann. 425, 217, 1921.
(5) C. Courtot, Ann, chim. [9] 4, 58, 1915.
(6) C. Engler and W. Frankenstein, Ber. 34, 2933, 1901.
(7) A. Klages, Ber. 40, 2360, 1907.
(8) A. Klages and F. Sommer, Ber. 39, 2306, 1906.
(9) H. Rupe and F. Emmerich, Ber. 41, 1393, 1908.
(10) F. W. Semmler, K. G. Jonas, and K. Oelsner, Ber. 50, 1838, 1917.
(11) F. W. Semmler, K. G. Jonas, and A. Roenisch, Ber. 50, 1823, 1917.
(12) J. Thiele, Ber. 33, 666, 1900.
(13) J. Thiele and H. Balhorn, Ann. 348, 1, 1906.
(14) R. Willstatter and M. Heidelberger, Ber. 46, 517, 1913.
X. CYCLOTRIENES OR CYCLOTRIOLEFINS, C n H 2n _ 6
441
X. CYCLOTRIENES OR CYCLOTRIOLEFINS, C.H,.., C,H,
Name and Carbon Skeleton
MT) O /"
, r., C.
B. P., C.
@ 760mm
D?
-s
Additional Data
Cycloheptatriene-1,3,5
(Tropilidene)
116 5
0.8929
115.5 to
@ 17,5
116.5
0.9129 8
114*
117 4
0.9082 .M
@ 724mm
@0
4,5,7,7-Tetramethyl-
heptatriene-1,3,5
or
5-Methylene-4,4,7-tri-
methylheptadiene-1 ,3
c c
67 to 68
0.8687
1.50660 8
Q\ ^-<^s.
@ llmm
or / T \.
c v_^
c c c c
(1) K. v. Auwers and F. Eisenlohr, Ber. 43, 827, 1910.
(2) A. Ladenburg, Ann. 217, 74, 1883.
(3) H. Rupe and W. Kerkovius, Ber. 44, 2702, 1911.
(4) R. Willstfltter, Ann. 317, 260, 1901.
(5) R. Willstatter, Ber. 34, 129, 1901.
XL DICYCLENES OR DICYCLOOLEFINS
1. Dicyclenes with alkyl substitutions, CnH 2 n_8
2. Dicyclenes with an alkyne substitution, C n Hj n _io
445
1. DICYCLENES WITH ALKYL SUBSTITUTIONS, C n H 2M _ 8 C,uHu
Name and Carhon Skeleton
M. / > ,/ C.
n. /., c.
(& 760iuin
D?
w :%0
"/>
AddilwHttl Data
1-Cyclopenten-l-
ylcyclopentene-1
(1,1 '-Dicyclopentenyl)
208 *
O-Ci
C I2 H 18
1-Cyclohexen-l-
ylcyclohexene-1
(1,1 '-Dicyolohexeny 1 )
28 2
245 to 251
0.9485 '
1.5287
250 to 253
oo
120 to 125
@ 15mm
l-Cyclohexen-2-
ylcyclohexene-2
(2,2'-Dicyclohexenyl)
234 3
0.9293 3
1.50903
*Author states that
"The hydrocarbon
was apparently an
octahy drod i p h e n y 1
which was isomeric
O-O
with the one having
conjugated double
bonds which has
been described by
Wallach.' 1
l-Cyclohexen-3-
ylcyclohexene-3
(3,3'-Dicyclohexenyl)
230 to 232
o-o
446
Name and Carbon Skeleton
M. F.,C.
B. P., C.
760mm
Iff
-s
Additional Data
2-Methyl-5-isopropyl-
l-(2-methyl-5-isopro-
pylcyclohexen-1-yl)-
cyclohexene-1
c c
90 to 195 ifl
.945 10
.5172 10
/~C VA
@30mm
p-Q
C-C 0-0
1 1
c c
1 ,2-Di-(2,6,6-trimethyl
cyclohexen-1-yl)-
ethane
(Di"/3-cyclogeranyl)
116^
C C
/-^ cc VA
/\ /\
C C C
447
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
8
Additional Data
1 -Methyl-6-cyclo-
hexylidenecyclo-
hexene-1
130 to 132 4
0.9282 4
1.5165 4
vl
0.9432 4
1 -Ethyl-6-cy clohexyli-
denecy clohexene- 1
139 to 141 4
0.9308 4
1.5172 4
x rS
@ 20mm
0.9461 4
3 ,3 '-Dimethyldicyclo-
hexenyl-x,x
265 to 267
448
q M cs
ON <
O
g
8
1
a
cl
449
Name, arid Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
It?
?>
Adtlituwnl Vati *P
i -Cycloocten- 1 -y Icy clo
octene-1
(I,r-Dicyclo6ctenyl)
36 to
115 to 116 7
0.9630 7
1.5353 7
O^^-s^
37 7
@ 0.25mm
@21.8
@24
-C
(1) K. Alder and H. F. Rickert, Ber. 71, 373, 1938.
(2) E. de B. Barnett and C. A. Lawrence, J. Chem. Soc. 1935, 1104.
(3) D. S. Frederick, H. D. Cogan, and C. S. Marvel, J. Am. Chem. Soc. 56, 1815, 1934.
(4) C. E. Garland and E. E. Reid, J. Am. Chem. Soc. 47, 2333, 1925.
(5) M. Godchot and G. Cauquil, Compt. rend. 186, 767, 1928.
(6) R. Kuhn and M. Hoffer, Ber. 67, 357, 1934.
(7) L. Ruzicka and H. A. Boekenoogen, Helv. Chim. Acta, 14, 1319, 1931.
(8) J. H. C. Smith, J. Biol. Chem. 90, 597, 1931.
(9) O. Wallach, Ann. 381, 95, 1911.
(10) O. Wallach, Ann. 403, 73, 1914.
C,,H, 4 450
2. DICYCLENES WITH AN ALKYNE SUBSTITUTION, C.H,._
Name and Carbon Skeleton
A/. r.:c.
fl. P., C'.
(r/j 7(>()tnrn
or
"7,
Additional Data
Dicy clopen ten- 1 -
ylacetylene
O-O
58.5 to
60
105 to 110>
@ 2mm
Cyclohexen-1-yl-cyclo-
penten-1 -ylacetylene
O-O
103 to 104
@2.5mm
0.9610'
1.5582 a
Dicyclohexen-1-
ylacetylene
Of/ \
158 to 159 4
0.9934 3
1.5520 3
-05H=0-^ \
@ 12mm
0.9604 4
1.5549 2
\ /
126 to 128 '
#1 3 3
1. 55768 4
@3mm
% 13
105 to HO 2
@ 1.5mm
(1) P. S. Pinkney and C. S. Marvel, J. Am. Chem. Soc. 59, 2669, 1937.
(2) P. S. Pinkney, G. A. Nesty, D. E, Pearson, and C. S. Marvel, J. Am. Chem. Soc. 59, 2666, 1937.
(3) P. S. Pinkney, G. A. Nesty, R. H. Wiley, and C. S. Marvel, J. Am. Chem. Soc. 58, 972, 1936.
(4) Ju. Salkind and N. Schuwalow, J. Gen. Chem. (U.S.S.R.) 7, 1235, 1937.
XII. BICYCLENES OR BICYCLOOLEFINS
1. Bicyclenes with alkyl substitutions, C, t H 2 ,_4
2. Bicyclenes with an alkenyl substitution, C W TI 2 .B
453
1. BICYCLENES WITH ALKYL SUBSTITUTIONS, C.H.,-4 CH 8
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
Iff
^
Additional Data
[0,2,2]-Bicyclo-
hexene-x
230 to 232
1038mm<
*- 9lll4
3,4,4-Trimethyl-
[0,l,3]< l .-bicyclo-
hexene-1
or
2 ,3-Dimethylene-
1,1-dimethylcyclo-
pentane
">1 V C c'
127 to 128 9
0.8292 9
O\ or /Y
@ 757mm
@0
~< p V '
c
d-l-Methyl-4-iso-
propyl-[0,l,3]<*.>-bi-
cyclohexene-1
lag - +37.69 "
tag- +35.54"
(-Thujene)
152 to
0.8314 I02
1.4502 102
c
c-c-c
152.5 "> 2
@ 699mm
151 to 152 7
151 to 152
755mm
0.8262
77 ao
0.8294 85
@ 17.4
30
1. 44909 7
1,45182 s *
@ 15.65
1. 44904 M
a
1. 45864
1. 46434 M
-
454
Name and Carbon Skeleton
M. P.C.
B. P., C.
@ 760mm
D?
3
Additional Data
M-Methyl-4-iso-
W=-4.23""
propyl-[0,l,3].>-bi-
cyclohexene-1
1-5- -.-.
(o-Thujenc)
152 to
0.8263 IM
1.45022
fa]g=- 37.20 ll2
152.3 no
{109.
(109
151 to 153 109
no
.10
151 to
0.8301 *
1.45150 2
152.5 109
151 112
@ 759mm
d-3-Methyl-6-iso-
La] j,- + 109.90 M
propyl-[0,l,3] <*>-
bicyclohexene-1
[aj > = +1 10.780 1K>
(/3-Thuiene)
147.5 to
0.8232 ll
1.44842 110
149.5 68
@22
@22
C
I
150 to 151 ll
0.8208 112
1.44708'"
o-c
@ 750mm
0.8248
1.44809"
X fC^l
147 112
0.8220 68
16
L\ J
@, 739mm
16
^AX\
c
CT Xlto
[1,2,21 < 3 - 6 >-Bicyclo-
heptene-1
(Norbornylene)
51 to
53 M
455
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
g
Additional Data
4-Methyl-[l,2,2]<'>-
Wcycloheptene-1
( 1 -Methylnorcamphene-4)
115.5 to
0.8668 12
1.4606 180
117 12
@ 18
18
@ 750mm
I
C
3,3-Dimethyl-
[1,2,2] (14 >-bicyclo-
heptene-1
(Camphenilene)
26.5 1M
138to 140 104
0,8699 IW
1.4676 1W
xf^s.
142 49
@21
@21
C \S
C
456
ivfy <*U
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
DP
B
Additional Data
1,2-Dimethyl-
[1,2,2] < 36) -bicyclo-
heptene-1
(San tone)
140 to 142 *
0.863 20
.46539 20
140 to 141 "
0.865 20
.4663 20
C
139 to 140 "
0.8700 69
.4688
/^/
136 to 140 9
@17
@17.5
L CN J
38 to 39
0.8720 94
1.4699 6
\^
@ 15mm
@17
@17.5
0.8664 4
1.4657 94
0.8698 5
1. 46758 59
0.871 69
1.4676 94
0.8710"
1.4710 94
0.8657 6
0.8680 94
a-Santene
140"
0.870 "
4,4-Dimethyl-
[1,2,2] < 3 >-bicyclo-
heptene-1
(Apoisofenchene)
24.5 to
25
134.5 to
135.5
0.8607 M
1.45764 86
@26
@ 762mm
0.8631
1.46111 M
140 to 142 6
0.8642 w
1.46023"
/\
136 to 138 u
C C
457
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
-8
Additional Data
7,7-Dimethyl-
[1,2,2] (36) -bicyclo-
heptene-1
(Apobornylenc)
36 to
135 to 140
0.8543 56
1.45374"
37 tt3
138"
@38.7
38 73
130 to 132 6
1. 45942 M
@ 742mm
1.45151 73
n 8.7
1. 45998
H f
1.46881 73
, !;
7,7-Dimethyl-
[1,1,3] < 4 6) -bicyclo-
heptene-1
(Apopinene)
14Q68
0.870 M
1.46700"
458
Name and Carbon Skeleton
M. P.,C
B. P., C.
^ 760mm
0r
Wg
Additional Data
1,4,4-Trimethyl-
M-+ 15.21 3
[0,l,4]< 3fi >-bicyclo-
heptene-1
WJ--f62.2w
(Carcne or Pinonenc)
172 to 173 '
0.8441 87
1.4717
WJ-+5.37 04
167 to 170
@30
@30
C
165.5 to 167 7
0.8552 7
1.4731 w
[a] yj = +82.64 * 7
r^^A
@ 707mm
/?30
@30
\^7
165 to 170 7
0.8594 10
1 47536 *
^x\
@ 685mm
Z) 27
c c
64 @ 29mm 87
0.8568 3
0.8561 4
1,5,5-Trimethyl-
|a| D =-f 14.45 U 9
[0,1,4] <<>-bicyclo-
heptene-1
fCareno or IscxHprene)
170 21
0.8586 I0
1 469 >oo
C
165 to 172 M
D 30
30
163 to 167 *
0.8575 87
1.4737"
/^
168 to 169 1W >
25
1. 47009
L)
@ 705mm
0.8571 <
18
/\^
123 to 124 10
0.8563 w
c c
@ 200mm
0.861 <
60 @, 30mm 87
o5!
0.8610 4
18
0.8668 21
D 16
459
Name and Carbon Skeleton
M. P.,C.
B. P., C.
760mm
or
n-
Additional Data
d-l,7,7-Trimethyl-
1.466 2
Mj, -+ 53.75 76
heptene-1
[a] I) -4-51.52
(d-a-Pinene)
156 to 157 43
0.8542 87
1.4634"
[al^- +51.14 1M
763mm
25
25
C
158.5 to 159 8S
0.8543 113 *
1.4635 113 *
[a]^- + 48.85 23
156 to
25
25
156.5 105
0.8582 42
1 .4645 87
laJ^" +47.9
156.0 to 96
25
25
[<*]-+ 47.89 7
156.1
0.8595 88
1.4608 105
156 33
x6
1. 46565 33
[a] . -f 47.48
155 to 159 75
0.8584 loa
1.4663 79 - 100
155 to' l08 - 107 -
0.8585 3 - 30
1.470 7f -
H^ -+ 33.37 '
156 108 - U3
155 17
0.8591 1M
0.8597 79
1. 46634 s
18.05
[cr]^- +15.47 088
154.5 to 155 79
0.8624 **
1.4663 43
[a]"- + 45.04 30
156.4 to
n*
^20
15
1 D
156.6 8
0.8594 8
1.4684 96
[]- +41.32 08
757tnm
15
@ 18.05
156 30
753mm
0.8620 23 - 4:)
15
1.4685 m
15
Reference 23 gives re-
fractive indices for
62 @ 30mm 7
44 14mm 17
45 1 2mm 3
0.8631 i)fi
15
0.8642 3 3
1.4691 5 17
14
1 .46929 30
13.8
mercury lines.
'"Average of four de-
terminations
15
1.4650 23
on same sample.
0.8643 *
@1?
15
if,
dii
-- fi 0004. /C"*
1.46354 s
0.8654
^18.06
dt (15 to 25)
15
a
1
0.8658 88
1.47322
W W.05
0.8591
1.47925 s
I
14
n ri
0.8694 w
7
n l
UIQ
0.8732 M
z?S
0.8740 M
4
0.8703 17
0.8746 30
460
Name and Carbon Skeleton
if P f
JXL, Jr., \f.
B. P., C.
760mm
*
*5
Additional Data
M,7,7-Trimethyl-
K- -46.65-
heptene-1
K--43^-
(/-a-Pinene)
156 to 157 32
0.8107 "
1.44797
[] 1> --42.6"
156"
155 to 156J| W
78.59
0.8259
61.4
61.4
1.45239
53.2
Wjj- - 40.51 l
WS- 1 - - 34.01 8
155"
153.3
157.1 to
157.4 8
757.5mm
0.8277
59.38
0.8327
53.2
0.8439
1.4625 10
28
1.4648 91
25
1.4687"
@9co
[a]JJ- -40,30"
Reference w has re-
fractive indices for
153.5 to
154.5
39.74
0.8525 '*
ZO
1. 46506 l5
24.1
mercury lines.
755mm
#"
1.46526"
155.4 to
0.8590 8fl
@ 23.5
155.8"
Dll
1.4606 22
@ 748.9mm
0.8565 16
1.4660 32
153tol54">
24.1
1.4676
700mm
0.8570 15
1.46803 8
23.5
16.25
0.8582
1.4649 23
0.8587 2
12
0.8598 18 - m
1.44523 16
0.8597 32
H *
1.44952 I6
I>20
w-
0.8621 8
16.25
a
1.46227 1S
0.8620 23
a
15
1.46252"
M 23.5
H
0.8654
a
15
1.465H 8
0.8685
n ii.
10
1.47202"
0.8749
W// i
1.47509"
W 16.26
0.8767 "
1.47779 I5
1. 48098 8
y
1.48122"
461
Name and Carbon Skeleton
M. P.SC.
7?, P., C.
(ft) 7(>0mm
Iff
2
Additional Data
dM,7,7-Trimethyl-
[1,1,3] '"-bicyclo-
heptene-1
(d/--Pinene)
155 to 156 2S
0.8108 M
1.46553 m
@ 764mm
@ 79.6
@21
159 to 161
0.854 l16
1.4662
155 to 160"
25
1.4664 1 "
fioe,
155 to 156j m
0.858 m
0.8592 IM
1.4662 >
@ 17.5
154.5 to 155 7
0.8593 "
1.43707"
@ 754mm
0.8583 "
a
153.5 to 154
@ 17.5
1.46324"
@ 750mm
0.8635 28
n 17 - 6
0.8586 w
1. 46736
Z) 16
WH !
0.8638 M
1.46741 2
@ 13.2
""*
1.44639"
1.47317 1
1.47631 ?8
1.47741"
w"- 2
1.45192"
W 7 8
t
1. 48332 s8
7
1.48341"
T
462
Name and Carbon Skeleton
M. P. t C,
n. P., c.
(fy 7 60mm
s
Additional Data
d-3,7,7-Trimethyl-
W| ,-+8J3-
heptene-1
(f/-8-Pinene)
156 to 159 7
0.8535 " 7
1. 46434 '
rOi
@ 748mm
c
1-3,7,7-Trimethyl-
H^-6.22""
heptene-1
156 to 158
0.8604 n7
1. 46672 7
@ 7 58mm
0.8708 79
@ 740.5mm
d/-3,7,7-Trimethyl-
[l,3,3]<.>-bicyclo-
heptene-1
157 to 159 w
0.8636 60
1.46561*
463
Name and Carbon Skeleton
B. P., C.
(Tn 760mm
/>r
s
Additional Data
d-3,7,7-Trimethyl-
tt| w --H9.29" m
[1,2,2] < 3 ' 6) -bicyclo-
heptene-1
| /| + 19.33 ">
(//-Bornylene)
109 to
46 u.
109.5 '
46.5 1U
X^N
109 to
(a) 750mm
l/>
110 111
C
/-3,7,7-Trimethyl-
W /> --22.27 ar '
[1,2,2] < 3 ->-bicyclo-
heptene-1
[a] /) =-21.69' 3
(/-Bornylene)
J13 11,13,8
14535
|| /) = -18.45"
113 to
@ 750mm
to
H4 12
145.6 to 146 >
l]^= -23.94
@ 7 50mm
146 ll
@ 745.5mm
146 ' 3
@ 740mm
d/-3,7,7-Trimethyl-
[!,2,2]< 3 .>-bicyclo-
heptene-1
(Bornylene)
96 to
149 to 150 31 -
101. 5 to
102.5 M
103 w
105 "
464
Name and Carbon Skeleton
M. P.,C,
B. P., C.
(fr 760tnm
pr
nl
Additional Data
1,2,3-Trimethyl-
[1,2,2] <">-bicyclo-
heptene-1
( Methyl santenc)
151 to 152"
0.8560
1.45943
C
1 c
^ x
"Ox
c
1,7,7-Trimethyl-
[1,2,2] - 6 >-bicyclo-
heptene-1
.-+.-
(Isopinene)
154.5 to
0.8658
1. 470253
c
1
155.5
8
3,5,5-Trimethyl-
[1,2,2] <*.Mbicyclo-
heptene-1
[a]^ =*- 68.76 78
[a],,- -57.28
(5-Fenchcne, Isofenchene,
139 to 140
0.8376 w
1.4505 M
[] J> --55.4
Fenchylene, Isofenchylene)
@ 760mm
0.8381
@ 20.8
^^^
139 to 140 "
0.8397 "
.4486 * 4
c fx^l
138.5 to 141 M
0.8398
.4494 78
C C
140.5 to w
141.5
@ 740mm
140 to 141 ' 78
0.842 "
0.8433 M
.4502 w
.4505
.47439 ll
@ 740mm
66 to 70
465
Name and Carbon .Skeleton ^M. l\ t C.
B. P., C.
(a\ 760mm
Iff
s
Additional Dttta
1,4,4-Trimethyl-
[l,2,2]< 3 .>-bicyclo-
heptene-1
(y-Fenchene)
146 to 148 w
0.854
1.461 M
145 to 150
0.8547
1.46072"
C
^ o
1
145 to 147 4
@> 17
@ 17
0.855 fi5
1.461
x>
@17
@17
c c
CTT
11 -til 8
7,7-Dimethyl-l-ethyl-
W5,- +33.96 2
[ 1,1,3] ->-bicyclo-
heptene-1
(Methyl myrtenyl)
95.5 to 96 2
0.8697
@ 62mm
C-C
1
8
1,2,3,6-Tetramethyl-
[1,2,2] (3 - 6) -bicyclo-
heptene-1
( 1 ,4-Dimethylsantenc)
161 to 162 62
0.8520 M
1. 46073
C
c | c
c
466
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
tit
8
Additional Data
1 ,4,4,6-Tetramethyl-
[ 1,2,2] < 8 >-bicyclo-
heptene-1
( Methy 1-fl-Fenchene)
160 to 162 M
0.85205 M
1.46261
@ 20.5
C
C ^
x\
c c
C 12*120
7,7-Dimethyl-l-propyl-
[1,1,3] <'>-bicyclo-
!], +21. 97 "
heptene-1
(Ethyl myrtenyl)
73 to 73.5 M
0.8663 M
@ 10mm
c-c-c
1
CisHaa
7,7-Dimethyl-l-butyl-
[], +21.63
[1,1,3] <.>-bicyclo-
heptene-1
(Propyl myrtenyl)
88 to 89 w
0.8624 M
@ 10mm
c-c-c-c
1
467
Name and Carbon Skeleton
\f n or>
JML. Jt .) C.
B. P., C.
@ 760mm
*?
-8
Additional Data
4,7,7-Trimethyl-3-(3-
M D K'
methylbutyl)-
[1,1,3] .>-bicyclo-
Mj)- 4.97 10S
heptene-1
(Dihydrocaryophyllene)
140 o
0.8898 19
1. 49032 I9
@24mm
@19
1.4885=
126 8 <>
0.8893 20
@ 18
@ 15mm
@ 18
1.496 108
1 c-c-c-c
129 to 130 "
0.8965 "
c 1
@ 14mm
15
1.4921 M
c
131
@16
@ llmm
[0,x,;t]-Bicyclooctene
137.5 to
0.891 118
1 .48434 ll8
139 119
0.9097 1I9
4-Methyl-[2,2,2] <*>-
bicyclooctene-1
fcT^N
147.5 to
0.8955 6l
i.4763 61
i x c 1
149"
17
@ 17
^^
@ 756.7mm
c
468
Name and Carbon Sheldon
Af. P.,C.
B. P., C.
(rt) 760mni
tff
M 20
W
Additional Data
2,5-Dimethyl-[0,3,3J-
bicyclooctene-1
-CO-
167 M
0.8605 M
@24
1.4649 6 *
24
2,6(?)-Dimethyl-[0,3,3]-
bicyclo8ctene-2
54 to 60
0.8632 M
1.4663 60
@20mm
3,3-Dimethyl-
[l,2,3]'7>-bicyclo~
octene-1
(Endocamphene)
170.6 to
0.8957 M
1. 48442 "
171.6 "
@ 12.4
@12.4
/Cv
@ 744.5mm
G
469
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Z)J
-8
Additional Data
l-Methyl-[0,3,4]-
bicyclononene-3
(8-Methylhexahydroindene)
175 to 176 r
0.8879 CT
1.4825 27
cb
@ 761mm
@ 16.5
@ 16.5
[0,4,4]-Bicyclodecene- 1
(A l -0ctalin)
194 25
0.9009 M
1. 48504 26
CO
@ 771mm
189"
@ 768mm
197 to 199
0.9090
0.9103
0.9105
@ 19.7
n u
1.491 24 26
1. 49525 26
"3,
1. 50138 26
,,20
/7 .
1.50126
1.50752"
[0,4,4]-Bicyclodecene-2
(/raj-/3-Octalin)
185 4
0.893 "
1.4841"
CO
0.8970
^15.6
10 XX ii
470
Name and Carbon Skeleton
M. P.,C
j3 n or*
/>. P., C.
@ 760mm
n x>
Additional Data
[0,4,4]-Bicyclodecene-2
(cw-/9-Octalin)
76 to 78
0.915 50
1.4959 10
@ 15mm
22
^22
72 to 73 "
0.909 10
1.4902 10
@12mm
[0,4,4]-Bicyclodecene-2
190 to 192 71
0.901 71
1.491 "
@13
@13
0.910 71
[0,4,4]-Bicyclodecene-
(1,6)
(/ram-Octalin)
|90W
0.8723 M
1.4719"
^x\ ^x"v
186 to 188 B2
(0 25
25
1 II 1
0.8936
1.48429"
kAJ
19,5
471
C 10
Name and Carbon Skekton
M. JVC.
B. P., C.
@ 760mm
iff
-g
Additional Data
[0,4,4]-Bicyclodecene-
-34
190 to 191 70
0.8987 l21
1.4867 l
189 w
22.5
22.5
194 to 196"
0.8968 l21
1.4851 m
@ 749mm
21
21
88 to 89
0.81 70
1.4976"
@ 19mm
@ 20.0
1.4979"
88 to 89
0.9205 8
1.4993
@ 14mm
0.9200 w
17
79 @ 14mm 46
0.914 70
17
0.931 7
frans-[0,3,5]-Bicyclo-
decene-2
co
63.5 47
0.8996 47
1.487U"
l-Methyl-[0,4,4]-
bicyclodecene-3
c
84 to 86
0.9074 72
1.4916"
^XJX^\
@ 14mm
16.2
16.2
1 II l|
82 M
0.9098 72
1.4956"
\X\/
@ 14mm
16
16
78 to 80 72
0.9085 "
1.4943"
@12mm
15.2
15.2
0.9053 8fl
1.4939"
@15
472
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
D?
l
Additional Data
2-MethyHO,4,4]-
bicyclodecene-x
78 to 80 3
@ 13mm
l,2-Dimethyl-[0,4,4]-
bicyclodecene-3
c
98 to 103 *
0.9121 2
14975 M
c 1
@ 12mm
@ 16.7
16.7
'I^^KII
95 to 99 2
0.9153 2
1.4974 28
^NX^^"^
@ 10mm
@ 16.4
@ 16.4
2,5-Dimethyl-8-ethyl-
[0,4,4]-bicyclodecene-
c
/^\
247 to 248 2
/Cu
c-c 1
c
2 ,8-Dimethyl-5-iso-
propyl-[0,4,4]-bicyclo-
decene-2
( Dihy drocadinene)
102 to 106
0.8944
1.4915 62
C
1
^\x^
@4mm
25
@25
/^^^^
c I
c-c-c
473
Name and Carbon Skeleton
Af. P.fC
B. P., C.
@ 760mm
iff
ng
Additional Data
2-Ethyl-3-propyl-
[0,4,4]-bicyclodecene-2
(l,2,4a,5,6,7,8,8a-Octa- "
hydro-3--propyl-4-
ethylnaphthalene)
89 to 90 84
@ 2mm
0.8913"
1.4838 M
C-C
1 c-c-c
ca
6, 10-Dimethyl-3-iso-
propyl-[0,3 ,S]-bicyclo-
decene-9
(Octahydroguaiazulene)
C
c 1
\ ^c-cj
123 to 125 9S
@ llmm
0.8872 9S
1.4834"
c
2-Propyl-3-butyl-
[0,4,4]-bicyclodecene-2
(l,2,4a,5,6,7,8,Sa-Octa-
hydro-3-?j-butyl-4-w-pro-
pylnaphthalene)
109 to 110 "
@ 2mm
0.8849 8J
1 4830 ^
c-c-c
| c-c-c-c
oa
474
(1) B. Ahlstrom and O. Aschan, Ber. 39, 1441, 1906.
(2) A. Andreocci, Gazz. chim. ital. 25, 1, 452, 1895.
(3) B. Arbusov and B. M. Michailov, J, prakt. Chem. [2] 127, 1, 1930.
(4) O. Aschan, Ann. 461, 1, (1928).
(5) 0. Aschan, Ber. 40, 4918, 1907.
C6) O. Aschan, Oversigt. av Finska Vetenskaps-Soc. Forh. 51, 1, 1908.
(7) O. Aschan, Oversigt. av Finska Vetenskaps-Soc. Forh. 53A, No. 8, 5.
(8) K. v. Auwers, W. Roth, and F. Eisenlohr, Ann. 373, 267, 1910.
(9) A. Behal, Bull. soc. chirn. [3J 27, 402, 1902.
(10) W. Borsche and E. Lange, Ann. 434, 219, 1923.
(11) J. Bredt and J. Hilbing, J. prakt. Chem. [2] 84, 778, 1911.
(12) J. Bredt and W. Perkin, Jr., J. Chem. Soc. 103, 224, 1913; J. prakt. Chem. [2] 89, 209, 1914.
(13) J. Bredt and H. Sandkuhl, Ann. 366, 11, 1909.
(14) L. Briggs and W. Short, J. Chem. Soc. 1928, 3118.
(15) J. Bruhl, Ber. 25, 151, 1892.
(16) E. Buchner and K. Rehorst, Ber. 46, 2680, 1913.
(17) M. Detepine, Bull. soc. chim. [4] 7, 468, 1910.
(18) N. Demjanow and I. Lenarski, Bull acad, sci (U.S.S.R.) 1937, 1001.
(19) E. Deussen, Ann. 388, 136, 1912.
(20) E. Deussen, J. prakt. Chem. [2] 114, 63, 1926.
(21) G. Dupont, Ann. chim. [10] 1, 184, 1924.
(22) G. Dupont, Private communication [Beilstein suppl. Vol. 5, p. 77].
(23) G. Dupont and L. Desalbres, Bull. soc. chim. [4] 33, 1252, 1923.
(24) F. Ebel and M. Goldberg, Helv. Chim. Acta, 10, 677, 1927.
(25) F. Eisenlohr and R. Polenske, Ber, 57, 1639, 1924.
(26) G. Elliott and R. P. Linstead, J. Chem. Soc. 1938, 660.
(27) K. D. Errington and R. P. Linstead, J. Chem. Soc. 1938, 666.
(28) J. F. Eykman, Chem. Weekblad, 3, 701, 1906.
(29) F. Flavitsky, Ber. 12, 2354, 1879.
(30) F. Flavitsky, J. prakt. Chem. [2] 45, 115, 1892.
(31) A. Gandini, Gazz. chim. ital. 66, 357, 1936.
(32) T. Gaponenkov, J. Gen. Chem. (U.S.S.R.) 4, 1128, 1934.
(33) E. Gildemeister, H. Kdhler, through O. Wallach, "Festschrift," 429, Gotlingen, 1909.
(34) J, Harvey, I. Heilbron, and E. Kamm, J. Chem. Soc. 1926, 3136.
(35) G. Henderson and W. Caw, J. Chem. Soc. 101, 1416, 1912.
(36) G. Henderson and E. F. Pollock, J. Chem. Soc. 97, 1620, 1910.
(37) T. Henry, J, Chem. Soc. 79, 1144, 190L
(38) D, C. Hibbit and R. P. Linstead, J. Chem. Soc. 1936, 470.
(39) D. C. Hibbit, R. P. Linstead, and A. F. Millidge, J. Chem. Soc. 1936, 478.
(40) F. Hofmann and P. Damm, Kaiser- Wilhelm Soc. 2, 97, 1925.
(41) R. Horiucki, Mem. Coll. Sci. Kyoto Imp, Univ. Ser. A. 11, No. 3, 171, 1928.
(42) J. Hosking, Rec. trav. chim. 47, 578, 1928.
(43) J. Hosking and W. Short, Rec. trav. chim. 47, 834, 1928.
(44) W. Huckel, Ber. 58, 1449, 1925.
(45) W. Huckel, R. Danneel, A. Schwartz, and A. Gercke, Ann. 474, 121, 1929.
(46) W. Huckel and H. Naab, Ann. 502, 136, 1933.
(47) W. Htickel and L. Schnitzspahn, Ann. 505, 274, 1933.
(48) V. N. Ipatieff, Ber. 43, 3383, 1910.
(49) W. Jagelki, Ber. 32, 1498, 1899.
(50) R. Jones and R. Linstead, J. Chem. Soc. 1936, 616.
(51) B. Kasansky and A. Plate, Ber. 68, 1259, 1935.
(52) S. Kimura, Mem. Coll. Sci. Kyoto Imp. Univ. Ser. A, 14, 173, 1931.
(53) G. Komppa, Ann. 472, 179, 1929.
475
(54) G. Komppa and S. Beckmann, Ann. 512, 172, 1934.
(55) G. Komppa and T. Hasselstrdm, Ann. 497, 116, 1932.
(56) G. Komppa and T. Hasselstrdm, Ann. 502, 272, 1933.
(57) G. Komppa and T. Hasselstrom, Ann. Acad. Sci. Fennicae, 26A, No. 1, 3, 1927.
(58) G. Komppa and T. Hasselstrdm, Ann. Acad. Sci. Pennicae 30A t No. 14, 3, 1930.
(59) G. Komppa and S. V. Hintikka, Bull, soc, chim. [4] 21, 13, 1917.
(60) G. Komppa and A. Klami, Ber. 70, 788, 1937.
(61) G. Komppa and G. Nyman, Ann. 517, 105, 1935.
(62) G. Komppa and G. Nyman, Ann. 518, 204, 1935.
(63) G. Komppa and R. Roschier, Ann. 429, 175, 1922.
(64) G. Komppa and R. Roschier, Ann. 470, 129, 1929.
(65) G. Komppa and R. Roschier, Ann. Acad. Sci. Pennicae 10A, No. 1, 62, 1917.
(66) G. Komppa and R. Roschier, Ann. Acad. Sci. Fennicae 10A, No. 15, 1, 1917.
(67) J. Kondakow, Chem. Z. 26, 720, 1902.
(68) I. Kondakow and V. Skeworzaw, J. Russ. Phys. Chem. Soc. 42, 497. 1910.
(69) A. Labo, Riv. Ital. delle essence and profumi, 7, 19, 1925.
(70) H. Leroux, Compt. rend. 141, 953, 1905.
(71) H. Leroux, Ann. chim. phys. [8] 21, 458, 1910.
(72) R. P. Linstead, A. Millidge, and A. Waipole, J. Chem. Soc. 1937, 1140.
(73) P. Lipp and J. Daniels, Ber. 69, 586, 1936.
(74) P. Lipp, A. Gdtzen, and F. Reinartz, Ann. 453, 1, 1927.
(75) E. Lynn, J. Am. Chem. Soc. 41, 361, 1919.
(76) K. Menon and J. L. Simonsen, J. Indian Inst. Sci. 10A, 1, 1927.
(77) W. Muller, Arch. Pharm. 238, 66, 1900.
(78) S. S. Nametkin, J. prakt. Chem. [2] 106, 26, 1923.
(79) S. S. Nametkin, J. Russ. Phys. Chem. Soc. 54, 177, 1922.
(80) S. S. Nametkin and L. Brussova, J. prakt. Chem. [2] 112, 169, 1926.
(81) S. S. Nametkin and E. Glagoleff, Ber. 62, 1570, 1929.
(82) S. S. Nametkin and V. Madajew-Ssitschew, Ber. 59, 370, 1926.
(83) S. S. Nametkin and A. Rushezewa, J. Russ. Phys. Chem. Soc. 51, 152, 1919.
(84) G. A. Nesty and C. S. Marvel, J. Am. Chem. Soc. 59, 2662, 1937.
(85) G. Ostling, J. Chem. Soc. 101, 468, 1912.
(86) J. Owen and J. L. Simonsen, J. Chem. Soc. 1931, 3001.
(87) R. Padmanabhan, and K. Jatkar, J. Am. Chem. Soc. 57, 334, 1935.
(88) W. H. Perkin, Sr., J. Chem. Soc. 81, 292, 1902.
(89) W. Qnist, Ann. 417, 278, 1918.
(90) G. Ramage and J. Simonsen, J. Chem. Soc. 1938, 1208.
(91) J. Riban, Ann. chim. [5] 6, 1, 1875.
(92) H. Rupe and A. H^ritier, Ann. 459, 171, 1927.
(93) L. Ruzicka, D. R. Koolhaas, and A. H. Wind, Helv. Chim. Acta 14, 1151, 1931.
(94) L. Ruzicka and F. Liebl, Helv. Chim. Acta 6, 267, 1923.
(95) L. Ruzicka and E. Rudolph, Helv. Chim. Acta 9, 118, 1925.
(96) A. Schorger, Ind. Eng. Chem. 6, 631, 1914.
(97) N. Schuickin, Uchenge Zapiski Saratov. Gosudarst. Univ. 3, 197, 1934,
(98) F. W. Semmler and K. Bartelt, Ber. 40, 4844, 1907.
(99) F. W. Semmler and H. Schiller, Ber. 60, 1591, 1927.
(100) J. L. Simonsen, J. Chem. Soc. 117, 570, 1920.
(101) J. L. Simonsen, J. Chem. Soc. 119, 1644, 1921.
(102) J. L. Simonsen, Indian For. Rec. 9, 289, 1923.
(103) J. L. Simonsen, "The Terpenes," Vol. 2, p. 520.
(104) P. Snitter, Bull. inst. Pin [2] 1933, 178, 200.
(105) F. H. Thurber and L. J. Roll, Ind. Eng. Chem. 19, 739, 1927.
(106) F. H. Thurber and R. C. Thielke, J. Am. Chem. Soc. S3, 1030, 1931.
476
(107) W. Treibs and H. Schmidt, Ber. 61, 459, 1928.
(108) D. Tsakalotos, Chem. Z. 32, 365, 1908.
(109) L. Tschugaev, Ber. 34, 2276, 1901.
(110) L. Tschugaev, Ber. 37, 1481, 1904.
(111) L. Tschugaev and W, Budrick, Ann. 388, 280, 1912.
(112) L. Tschugaev and W. Pomin, Ber. 45, 1293, 1912.
(113) M. Vezes, Bull. soc. chim. [4] 5, 931, 1909.
(114) O. Wallach, Ann, 239, 1, 1887.
(115) O. Wallach, Ann. 258, 319, 1890.
(116) O. Wallach, Ann. 300, 294, 1898.
(117) H. Wienhaus and P. Schumm, Ann. 439, 20, 1924.
(118) R. Willstatter and T. Kametaka, Ber. 41, 1480, 1908.
(119) R. Willstatter and H. Veraguth, Ber. 40, 957, 1907.
(120) N. D. Zelinsky, B. A. Kasansky, and A. F. Plate, Ber. 66, 1415, 1933.
(121) N. D. Zelinsky and M. B. Turova-Pollak, Ber. 58, 1292, 1925.
477 C : H
2. BICYCLENES WITH AN ALKENYL SUBSTITUTION, C n H 2n -e
Ndtnc an-d Carbon Skeleton
M. /./'(.
($ 700mni
I)?
3J
Additional Ihda
5-Methylene-4,4-di-
methyl-[l,2,2] <'.>-
bicycloheptene-1
( Isocamphodiene)
41.5 to
149 to 150
^
42
@ 763mm
C /\
C C
C* TT
6-Methyl-9-isopropyli-
dene-[0,4,4]-bicyclo-
decene-2
c
125 to 126 J
0.9124
1.5065 7
1
c-c
@ 12mm
@18
18
c
4,7,7-Trimethyl-3-(3-
methylbuten-3-yl)-
{<*]%=- 8.959"
[a]J-8.95
heptene-1
[a]M=-8.5to9.5 ie
(0-Caryophyllene)
258 to 259 '
0.9038
1.49976 18
@ 752mm
@24
1.50076 *
fOc?]
136 to 137 "
0.9032 8
1.49694"
Ic'l J C
@ 20mm
0.9030 1S
w 20
| C-C-C=C
c
129 to 130
@ 14mm
D 20
0.9076 "
1.50830 "
n 50
136 to 137 "
@ 15
"ft
@10mm
1.51528 "
119^120'
^
@9mm
478
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
Iff
-B
Additional Data
4,5-Dimethyl-5-(4-
[],,- -41.3
methylpenten-3-yl)-
heptene-1
(0-Santalene)
263 to 264 3
0.8940 12
1. 49460 l2
125 to 126 12
0.9139 8
c-oc-c-c |\j
@ 7mm
01
I ")>x!x
c |
c
3,7-Dimethyl-10-iso-
241^
propenyl-[0,4,4]-bicyclo-
decene-3
(Micranene)
266 to 268 6
0.9155 6
1.5050
126 to 128 6
30
@30
c=oc
1 c
@ 5mm
CO"
\X^^s/
1
c
3,10-Dimethyl-7-
[a]g- -51.36"
isopropenyl-[0,4,4]-
bicyclodecene-2
WD--
(Isozingeberene) *
138 @ 20mm 8
130 to 135
0.9070 '
0.9118"
1.5030 8
1.506 9
*Correct structure of
this seems to be 3,7-
C
1 c
ay
. @ 14mm
120 to 123"
@8mm
118 to 122"
0.9150 "
0.910- 9
@15
1.5062 "
1.5034"
Dimethyl-5 -isopro-
pyl-[0,4,4]-bicyclo-
decadiene-2,8. See
Simonsen,"TheTer-
penes," p. 498, Cam-
T
@7mm
bridge Press, Lon-
don, 1932.
479
Name and Carbon Skeleton
M. JVC
B. P., C.
@ 760mm
0?
5
Additional Data
9-Methylene-5-methyl-
2-isopropyl-[0,4,4]~
bicyclodecene-2
(y-Cadinene)
c-c-c
CX CD
266 <
0.9089 4
@30
1.5021
@30
^^ ^^^
c
2,6-Dimethyl-9-iso-
propenyl-[0,4,4]-bicyclo-
decene-2
W^- -1-61.6"
[ak=+49.5
(a-Selinene)
268 to 272 "
0.9190 l5
1.5048"
W-+32 010
C
1 c
c=c 1
X CO
133 to 134.5 10
128 to 132 18
@ 11 mm
0.9196
0.9232 "
15
0.9203 10
13
1.50920"
1.5075 10
@13
c
(1) E. Erdmann, J. prakt. Chem. [2] 56, 143, 1897.
(2) J. Gadamer and Amenomiya, Arch. Pharm. 241, 22, 1903.
(3) M. Guerbet, Compt. rend. 130, 1324, 1900.
(4) K. Kafuku, K. Ikida, and Y. Pujita, J. Chem. Soc. Japan 53, 636, 1932.
(5) K. Kafuku, K. Ikida, and Y. Pujita, J. Chem. Soc. Japan 56, 1186, 1935. '
(6) S. S. Nametkin and A. Zabrodina, Compt. rend. (U.R.S.S.) 1937, 1015.
(7) L. Ruzicka and E. Capato, Ann. 453, 62, 1927.
(8) L. Ruzicka, J. Meyer and M. Mingazzini, Helv. Chim. Acta 5, 345, 1922.
(9) L. Ruzicka and A. G. van Veen, Ann. 468, 143, 1929.
(10) L. Ruzicka, A. H. Wind, and D. R. Koolhaas, Helv. Chim. Acta 14, 1132, 1931.
(11) Schimmel and Co, Chem. Zentr. 1910, 1, 1719.
(12) Schimmel and Co. Berichte for Oct. 1910, 106.
(13) 0. Schreiner and E. Kremers, Pharm. Arch. 2, 281.
(14) P. W. Semmler and A. Becker, Ber. 46, 1814, 1913.
(15) P. W. Semmler and P. Risse, Ber. 45, 3301, 1912.
(16) J. L. Simonsen, "The Terpenes," Vol. 2, p. 515. London, Cambridge University Press, 1932.
(17) H. Thorns, Arch. Pharm. 241, 592, 1903.
XIII. BICYCLODIENES OR BICYCLODIOLEFINS
483
BICYCLODIENES
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
DT
5
Additional Data
1,5,5-Trimethyl-
W,= -71.6
heptadiene-1,3
[ a ] D *- 1 00.61 3
(Verbenene) /
159 to 160 6
0.8822 5
1. 49800
@ 758mm
0.8852 8
1. 49855*
C
158 to 159 4
15
@ 749mm
0.885 4
C fO^
158 to 159
15
/^b?
745mm
0.8866 fl
C
45 @ llmm 8
15
d
158 to 159
0.8867
1.49800
(] yj = -}- 100.71
@ 745mm
15
1 ,3,5,5-Tetramethyl-
[l,l,3]< 4 ' 8 >-bicyclo-
heptadiene-1,3
(Methyl verbenene)
175 to 176 6
0.872 5
1.4969
771mm
0.876 *
C
1
49 8mm 8
15
\(5<h
c c
[0,3,4] < l ->-Bicyclo-
nonadiene-2,4
/^T^^
171 to 172 87
0.9274 w
1.5153
OJ
@ 757mm
16.5
@ 16.5
484
Name and Carbon Skeleton
M, P.,C.
R. P., C,
(m 760mm
D?
?j 20
2-Isopropyl-5,5,9-tri-
methyl-[0,3,4]<' >-bi-
cyclononodiene-2, (6, 10)
(Guaiene)
31.5 2
C |
\ 1
/\
c c
[0,4,4]-Bicyclo-
decadiene-2,5
^^Xx^^x
75 to 76 19
0.9726 18
1.5322"
^^^^
@ 8mm
[0,4,4]-Bicyclo-
decadiene-x,*
199.5 to 200
0.934 w
1.52618
197 w
D?
^ 16.4
195 1<J
0.95807 80
1.52879"
18.4
ft 18 * 4
a
0.94887 20
1.52215"
16.4
0.9419"
a
@o
1.54397"
0,952
W 18.4
**
#0
1.53648"
JJ- 4
1.55340 80
47 18. 4
W^
7
1.54555 so
7
Additional Data
485
v/u
Name and Carbon Skeleton
M. P ,C.
B. P., C.
@ 760mm
^
ng
Additional Data
6-Methyl-[0,4,4]-
bicyclodecadiene-1 ,3
r^^Y^
172 14
LJCJ
@ 12mm
c
C, 2 H 18
3-Ethyl-[0,3,5]-
bicyclodecadiene-2 ,4
r^v%-c-c
109 to 111 30
1.5252 M
u^
@ 10mm
l,4-Dimethyl-[0,4,4]-
bicyclodecadiene-*,*
(1,4-Dimethyl-
hexahydronaphthalene)
0.92194 20
@ 19.8
1. 50902
@ 19.8
1.50547*
n-
1. 51790 s0
1 ,2,4,5-Tetramethyl-
[0,4,4]-bicyclodeca-
( 1 ,2 ,4, 5-Tetramethylhexa-
hydronaphthalene)
89 to 91 33
@ 0.6mm
0.926 33
D5
1.5095"
486
Name and Carbon Skeleton
M. P. t C.
B. P., C.
@ 760mm
Iff
* D
Additional Data
d-3,7-Dimethyl-10-iso-
propyl~[0,4,4]-bicyclo-
[a]5-+ 103.7 32
decadiene-2,9
( a ]20__|_4gJ2
(Cadinene)
274 to 275 10
0.9225 31
1.5065 32
lag- +47.92
273 to 275 10
0.9255 32
1.5094 10
o-c-c
272 to 274 32
0.9193 13
1.5107 10
W0-+55 "
i^v^ /c
260 to 261 7
@1S
1.5108 7
i a i -4-50'
[ I J
269 31
0.9224 l
1.5065 l3
D
T^
@ 750mm
@15
@15
[ a ju aa 4-n.68 -"
1
c
153 to 154 7
0.9247 7
@26mm
@15
129 to 131 I3
@ 10mm
/-3,7-Dimethyl-10-iso-
propyl-[0,4,4]-bicyclo-
[ a ] D =- 130.0 "
decadiene-2,9
W jD =- 116.73 27
274 to 275 35
0.9183 26
1.50858 26
[ a ]^~l 10.96 17
272 to
@22
^22
275 *' 27 ' 84
0.918 18
1.50647
[a],,-- 105.5"
272
0.9183 17
1.5065* fl
la]^ -- 98.56 36
271 to 272 17
0.9185 "
1.50651 w
135 to 137 8
0.9293 8
1.5073 17
[ a ] ^-yp^ss
@ 15mm
@18
1.5074 1J
140 to 142 8
0.9229 27
1.5070 1
[a] /? =-74.6 01
@ llmm
@ 15
^ 15
135 >
0.9298 1
1.5096 3
[a]^-- 68.38 8
@ llmm
@15
@ 13
134 to 136 "
0.9246 8
[a^-- 30.82 8
@ llmm
D\l
127 to 128.5 25
.@6mm
487
Name and Carbon Skeleton
M. P. t C
B. P., C
760mm
tif
s
Additional Data
3,7-DimethyMO-iso-
W =-t.o'
propyl~[0,4,4]-bicyclo-
decadiene-2,(l,<5)
(Isocadinene)
124 to 128 18
0,9181 l2
1.5158"
c-c-p
@12mra
124 to 126"
0,9154 "
1.5150"
oo /c
@ llmm
\X\X
c
10,10-Dimethyl-3-iso-
propyl-[0,4,4]-bicyclo-
decadiene-2,(l,6)
(Bicycloisoprenernyrcene)
130 to 134 22
0.9136
1.5051 22
@ 13mm
@ 21
@ 21
c
C c |
V c-c
oa
488
Name and Carbon Skeleton
M.P.fC.
B: P., c.
@ 760mm
iff
^
Additional Data
2 ,6-Dimethyl-9-iso-
propyHO,4,4]-bicyclo-
decadiene-2,9 or -2,8
[ a j^ ^-fl 94.3 *
(o- or e-Selinene)
130 2
0.9234
1.5167 29
@ 12mm
@14
@14
C 9
\Xj\x^
C
rS-form
or
C
1" '
r^^^r^
\xn^\^
C
-form
Eudesmene
..-
W^-s 4-52.6 24
(Position of double bonds
132 to 136 24
0.9232 28
1.50987"
unknown)
@ 15mm
0.9214 23
1. 50874 M
M5-+51 "
Q
128 to 132 23
0.9204 28
1. 50738
fa]20 _ 4Q028
@ 12mm
0.91964 2e
1.5125
a D
C 4>f xs v x '^
129 to 132 2
0.9175 24
1.5 134 2
1 1 J
@ 10mm
@ 19
^s-XTX^
122 to 124 26
C
@ 7mm
121 to 123 *
@6mm
489
(1) P. Aitken, J. Soc. Chem. Ind. 47T, 223, 1928.
(2) K. Birrell, J. Am. Chem. Soc. 57, 893, 1935.
(3) W. Blackie, J. Soc. Chem. Ind. 48T, 357, 1929.
(4) A. Blumann and H. Schmidt, Ann. 453, 48, 1927.
(5) A. Blumann and 0. Zeitschel, Ber. 46, 1178, 1913.
(6) A. Blumann and O. Zeitschel, Ber. 54, 887, 1921.
(7) E. Deussen, Arch. Pharm. 240, 288, 1902.
(8) E. Deussen, F. Weiss, P. Hacker, and P. Hille, J. prakt. Chem. 12] 117, 273, 1927.
(9) C. Graebe and P. Guye, Ber. 16, 3028, 1883.
(10) E. Grimal, Compt. rend. 135, 1057, 1902.
(11) G. G. Henderson and A. Robertson, J. Chem. Soc. 125, 1992, 1924.
(12) G. G. Henderson and A. Robertson, J. Chem. Soc. 1926, 2811.
(13) J. L. Hosking and W. P. Short, Rec. trav. chim. 47, 834, 1928.
(14) W. Huber, Ber. 71, 725, 1938.
(15) K. Kafuku, K. Ikida, and Y. Fujita, J. Chem. Soc. Japan 53, 636, 1932.
(16) H. Leroux, Compt. rend. 151, 384, 1910.
(17) N. Lepeschkin, J. Russ. Phys. Chem. Soc. 40, 698, 1908.
(18) W. Lbssen and A. Zander, Ann. 225, 109, 1884.
(19) S. S. Nametkin and E. V. Glazoleva, J. Russ. Phys. Chem. Soc 61, 535, 1929.
(20) R. Nasini and O. Bernheimer, Gazz. chim. ital. 15, 59, 1885.
(21) E. Parry, "The Chemistry of Essential Oils and Artificial Perfumes," Vol. II, 83, 4th edition, 1922.
(22) L. Ruzicka and W. Bosch, Helv. Chim. Acta 14, 1336, 1931.
(23) L. Ruzicka and E. Capato, Ann. 453, 62, 1927.
(24) L. Ruzicka, J. Meyer, and M. Mingazzini, Helv. Chim. Acta 5, 345, 1922.
(25) F. W. Semmler and K. G. Jonas, Ber. 47, 2068, 1914.
(26) F. W. Semmler and F. Risse, Ber. 46, 2303, 1911.
(27) F. W. Semmler and H. Stenzel, Ber. 47, 2555, 1914.
(28) F. W. Semmler and E. Tobias, Ber. 46, 2026, 1911.
(29) J. L. Simonsen, "The Terpenes," Vol. 2, p. 512, London, Cambridge University Press, 1932.
(30) A. St. Pfau and PI. Plattner, Helv. Chim. Acta 19, 858, 1936.
(31) H. von Soden, Chem. Z. 33, 428, 1909.
(32) F. Thurber and L. Roll, Ind, Eng. Chem. 19, 739, 1927.
(33) F. Trost and V. Debelli, Ann. chim. applicata 26, 301, 1936.
(34) S. Uchida, J. Am. Chem. Soc. 38, 687, 1916.
(35) O. Wallach and E. Conrady, Ann. 252, 141, 1889.
(36) F. Wreden, J. Russ. Phys. Chem. Soc. 9, 183, 1877; Ber. 9, 1598, 1876.
(37) N. D. Zelinsky and P. Borissov, Ber. 57, 2060, 1924.
XIV. D1BICYCLENES OR DIBICYCLOOLEFINS, C,.Hi_io
493
XIV. DIBICYCLENES OR DIBICYCLOOLEPINS, C.H,..,. C,,H,,
Name and Carbon Skeleton
W. /'.,C'.
B. P., C.
(a> 70()inm
^
-s
Add if tonal Data
Di-(7,7-dimethyl-
1 1 , 1 ,3 ] (4 fi) -bicyclohepten-
WL- + I3.7W
l-yl)-methane
(Dimyrtenyl)
173 to 174 *
0.9521 2
SHE
@ 10mm
Pinaconene
,c-c-c c-c-c
\ /
55 to 56
0.93046 >
1. 50233
@61
\ /
. cc
(1) B. Beckmann, Ann. 292, 1, 1896.
(2) H. Rupe and A. Heritier, Ann. 459, 171, 1927.
XV. POLYCYCLENES, C B H 2n .
497
XV. POLYCYCLENES, CM,*-.
Name and Carbon Skeleton
M. P.,C.
3. P., C.
@ 760mm
tf/
ng
Additional Data
Dihydrodicyclopenta-
diene
r x TVA
4717
178 3
(c jr //
50 to 51 2
@ 766mm
VJx^^/
67 to 68 17
@ 14mm
78 to 80 "
@ 13mm
C 12 H 18
6,7-Cyclopentano-
[0,3,4]-bicyclononene-
(1,5)
(l,2,3,3a,4,5,6,7,8,8b-Deca-
107 to 108 6
0.9397 fl
1.4990*
hydro-as-indacene)
@ 17mm
L/13 JH.20
2 ,3-Cyclopentano-
[0,4,4]-bicyclodecene-
(1,6)
(1,2,3,4,5,6,7,8-Octahydro-
74 to 76 8
0.95 13"
1.5074 8
1 ,2-cyclopentano-
@ 3mm
naphthalene)
f^^^T^l
^^^^
C,,H,
498
Name and Carbon Skeleton
M.P,C.
B. P., C.
@ 760mm
tf
B
Additional Data
Decahydrofluorene
/ -/N-'-x
258 to 259 "
1.012 13
1.S060 1 *
/""YT-V^
% 745mm
Y_ ) \ /
258"
@ 73 7mm
254 4
@ 727mm
Cullza
A u -Dodecahydrophe-
nanthrene
x\
268 to 269 12
0.964 l2
1.5098'
1 J
@ 737mm
0.9674 8
1.5102 8
r^irV
81 to 82 8
1.5119 ia
Cu
@ 1 ,5mm
Copaene
[]^=- 13.21 "
c-c-c
246 to 251 10
0.9077 10
1. 48943 10
\/ x ^\^ x ^s.
119 to 120 14
15
K IT ^1
MJ
@ 10mm
^v^ ^^^
C
499
Name and Carbon Skeleton
B. P., C.
@ 760mm
/>r
-5
A dd if ion a I Data
Dodecahydroretene
(Double bond position not
336 6
0.8985 >
1.48510 >.'
indicated)
148 to 150
p.
@ 10mm
f xxXXs Y xX V X ^ \
T T C
oc
1
1
c
C20-H.34
7,7-Dimethyl-3,4-
(5-methyl-2-isopropyl-
cyclohexano)-[0,4,4]-
bicyclodecene-(l,6)
(1,2,3,4,4',5,6,7,8,9,9',10-
176 9
0.9410'
1.5118 9
Dodecahydro- 1 -isopropyl-
@ 12mm
14
14
4 ,5 ,5 -trimethylanthracene ,
Tricyclic camphorene
dihydride)
c-c-c
( xXS N xXX Y X i
\/^xx^\x^
C C C
500
(1) D. Adelson and M. T. Bogert, Chem. Rev. 24, 135, 1939.
(2) K. Alder and G. Stein, Ann. 485, 223, 1931.
(3) K. Alder and G. Stein, Ber. 67, 613, 1934.
(4) P. Guye, Bull. soc. chim. [3] 4, 266, 1890.
(5) C. Liebermann and L. Spiegel, Ber. 22, 779, 1889.
(6) P. S. Pinkney and C. S. Marvel, J. Am. Chem. Soc. 59, 2669, 1937.
(7) P. S. Pinkney, G. A. Nesty, D. E. Pearson, and C. S. Marvel, J. Am. Chem. Soc. 59, 2666, 1937.
(8) P. S. Pinkney, G. A. Nesty, R. H. Wiley, and C. S. Marvel, J. Am. Chem. Soc. 58, 972, 1936.
(9) L. Ruzicka and M. Stoll, Helv. Chim. Acta. 7, 271, 1924.
(10) Schimmel and Co., quoted by F. W. Semmler and H. Stenzel, Ber. 47, 2555, 1914.
(11) J. Schmidt and E. Fischer, Ber. 41, 4227, 1908.
(12) J. Schmidt and R. Mezger, Ber. 40, 4240, 1907.
(13) J. Schmidt and R. Mezger, Ber. 40, 4566, 1907.
(14) F. W. Semmler and K. Spornitz, Ber. 45, 1553, 1912.
(15) H. Staudinger and H. Bruson, Ann. 447, 97, 1926.
(16) A. Virtanen, Ber. 53, 1880, 1920.
(17) H. Wieland and F. Bergel, Ann. 446, 13, 1925.
XVI. CYCLYNES OR CYCLOACETYLENES, C n H 2
503
XVI. CYCLYNES OR CYCLO ACETYLENES, CH 2n _ C 7 H lfl
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
DT
-s
Additional Data
Cycloheptyne-1
(Suberoterpene)
120 to 121 l
O
-/15-H.js
Cyclopentadecyne
158 to 159 M
0.8843 i.
1.4910
@ 14mm
Cycloheptadecyne
127 to 128 2
0.8840 2
1.4869*
@ 0.25mm
22
(1) W. Markownikow, J. Russ. Phys. Chem. Soc. 34, 911, 1902.
(2) L. Ruzicka, M, Hurbin, and H, A. Boekenoogen, Helv. Chim. Acta 16, 498, 1933.
XVII. SPIRO-HYDROCARBONS
507
XVII. SPIRO-HYDROCARBONS
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D?
s
Additional Data
Cyclopropane-spiro-
cyclopropane
ex
39.5 to 40.5 6
@ 746mm
0.7266
1.4120
C 9 H 16
1 ,5-Dimethyl-cyclo-
butane-spiro-cyclo-
butane
c
132
0.7972 4
1.43459*
@ 756mm
@20.0
@20.0
c
1 , 1 ,6,6-Tetramethyl-3-
isopropyl-cyclobutane-
spiro-cyclobutane
c c
c /\ >x
116 to 118 4
@23mm
0.8380 4
@20.0
1.46362 *
@ 19.9
\/\/ \
/\/\/
c \^ \/
1
c-c-c
508
Name and Carbon Skekton
M. P.,C
B. P., C.
@ 760mm
Iff
ng
Additional Data
Cyclopentane-spiro-
cyclopentane
OO
60 @ 12mm 2
Cyclopentane-spiro-
cyclohexane
OO
185 to 186 8
@ 745mm
0.8877 8
1.4748 8
75 @ 20mm 3
5-(Cyclohexane-spiro-
cyclohexyl)-docosane
C-<C),-C-<C)i 6 -C
0.867 5
1.4793 6
509
io Hie
Name and Carbon Skeleton
M. P. t C
B. P., C.
@ 760mm
D?
-8
Additional Data
[0,l,3]< 10 >-Bicyclo-
hexane-spiro-cyclo-
pentane
189 to 190 7
@ 764.5mm
0.9134 7
17
< >o
C 12x120
l-Methyl-[0,2,4] <''<>>-
bicyclooctane-spiro-
cyclobutane
^X>s/
77 to 78 *
@ 13.5mm
0.8679 4
1. 46809 4
@ 20.0
C n H 2 n-6
C 9 Hi 2
*
1 ,5-Dimethylene-cyclo-
butane-spiro-cyclo-
butane
c
/\/\
135 <
@ 774mm
70.5 4
0.8264 4
@ 20.0
1. 48064 4
@20.0
w
@90mm
II
38 4
c
@21mm
510
Name and Carbon Skeleton
M. P. t *C.
B. P., C.
(& 760mm
off
"S
Additional Data
l-Methylene-5-methyl
5-isopropenyl-cyclo-
butane-spiro-cyclo-
butane
c
101*
0.9346 4
1.52624*
II
@ 10mm
@ 20.0
@ 20.0
oc c
1
c
CuHie
1-Methylene-
[0,2,4] < 7 .-bicyclo-
8ctene-7,10-spiro-
cyclobutane
X\
72 to 74 4
0.8955*
1.50301 *
^^\s
@20.0
@ 20.0
(1) N. N. Chatterjee, J. Indian Chcm. Soc. 13, 536, 1936.
(2) N. N. Chatterjee, J. Indian Chem. Soc. 14, 259, 1937.
(3) G. R. Ciemo and J. Ormston, J. Chem. Soc. 1933, 352.
(4) S. V. Lebedev and B. K. Mereshkowsky, J. Russ. Phys. Chem. Soc. 45, 1249, 1913.
(5) L. Mikeska, Ind. Eng. Chem. 28, 970, 1936.
(6) N. D. Zelinsky and W. Krawetz, Ber. 46, 163, 1913.
(7) N. D. Zelinsky and N. I. Schuikin, J. Russ. Phys. Chem. Soc. 62, 1343, 1930.
(8) N. D. Zelinsky and N. I. Schuikin, J. Russ. Phys. Chem. Soc. 62, 2180, 1929.
XVIII. HYDROCARBONS OF KNOWN BUT UNCLASSIFIED STRUCTURE
XVIII. HYDROCARBONS OF KNOWN BUT UNCLASSIFIED STRUCTURE
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
7)5
s
Additional Data
CnH.2n.-4
Cyclohexylcyclo-
hexylidenemethane
o-o
133
@ 20mm
111 toH2 5
0.8972 *
0.919 "
t.4908 6
@ 12mm
1 ,1-Dicyclohexylethene
,
c=c
1
O
1 ,3-Dicyclohexylcyclo-
hexene-1
O
204 to 207 I3
@ 15mm
514
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
z>r
-s
Additional Data
1 ,4-Dicyclohexylcyclo-
hexene-1
(T-Iexadecahy drotcrpheny 1 )
Ill to
190 2
113 2
@ 13mm
o-oo
Dicyclohexylcyclo-
hexen-1-ylme thane
OjO
41 10
Dicyclohexylcyclo-
hexylidenemethane
6
@ 10mm
515
C&HIO
Name and Carbon Skeleton
B. P., C.
(?r) 760mm
,r
5
Additional Data
1 -Ethynylcyclohexene-1
c^c
148 to 151 '
0.8800
.4922 l
1
145 to 146
.4978
40 to 43 s
@ 12mm
2,7,7-Trimethyl-
l-(2,7,7-trimethyl-
a} u ~ 4-28.47
aJ^-i-15.56 '
bicycloheptyl)-
[1,2,2] < 3 '>-bicyclo-
heptane
(Bis-[2,7,7-trimethyl-[l t 2,2]-
bicycloj-heptyl)
C C
/ \
948
85 to 87 6
75 <
74 to 75 7
326 to 327 4
322 to 323 7
321 to 323.6 8
188 to 190 7
@ 1 2mm
1.001
(solid)
1,2-Dicamphane ethane
c c
/ \
205 to 208 "
@ llmm
516
(1) Bayer and Co., Ger. Pat. 290,558.
(2) J. v. Braun, G. Irmisch, and J. Neltes, Ber. 66, 1471, 1933.
(3) W. Carothers and D. Coffman, J. Am. Chem. Soc. 54, 4071, 1932.
(4) A. fitard and G. Meker, Compt. rend. 126, 526, 1898.
(5) P. G. Fischer and O. Stoffers, Ann. 500, 253, 1932.
(6) A. Hesse, Ber. 39, 1127, 1906.
(7) J. Houben, Ber. 38, 3796, 1905.
(8) E. Letts, Ber. 13, 793, 1880.
(9) R. Levina and S. Levina, J. Gen. Chem. (U.S.S.R.) 8, 1776, 1938.
(10) O. Neunhoeffer, Ann. 509, 115, 1934.
(11) H. Rupe and J. Brin, Helv. Chem. Acta 7, 546, 1924.
(12) P. Sabatier and A. Mailhe, Compt. rend. 139, 343, 1904.
(13) W. Schrauth, W. Wege, and P. Banner, Ber. 56, 260, 1923.
(14) E, Venus-Danilova, J. Russ. Phys. Chem. Soc. 61, 1479, 192&
517
C,H,
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
nr
"8
Additional Data
Cyclooctatetraene
-27 43
42.2 to 42.4
0.925 44
1. 53944
approx.
@ 17mm
0.923
1. 54225
36.2 to 36.4
0.920 3
1.5389 44
@ 14mm
0.943 * 4
1. 53413
W 5? ft
1. 53659
a
1. 55377
1.55759 45
1. 57089
n u
i
1.57426
12
Cyclopentylidene-
cyclopentadiene
DO
55 to 57 w
@ 2mm
C 10 Hi a'
518
Name and Carbon Skeleton
M. P. t C.
B. P., C.
760mm
^
-s
Additional Data
2,5-Endomethylene-
bicyclo-[0,4,3]-nono-
diene-3,7
(Dicyclopentadienc)
32.9
163 l
0.9302
1.48031
^T^
32.5 41
766mm
77.25 C
wg- 26
CM)
32 1,31,33.36
169.5tol70<
0.9756
35
1.51047 M
95 55mm
88 35mm 17
70 24mm M
69 12mm 88
68 to 70 M
0.9766"
33
1.012"
17.5
(solid)
1.49121
1.52181 M
-8,
@12mm
1. 49766
W 77.S5
v/n Jtli4
Cyclohexylidene-
cyclopentadiene
oo
78 to 80 "
25mm
C 12 Ilia
[l,4]-Endoethylene-
[0,4,4]-bicyclodeca-
diene-3,7
rrTu
229 to 230 *>"
0.9944 *
1.5265 s
519
Name and Carbon Skeleton
Af. P. t C.
B. P., C.
@ 760mm
Iff
B
Additional Data
3,7,7-Trimethyl-
[0,4,4] < l >-bicyclo-
decatriene-2,4,8
(Irene)
127"
0.9402 w
1.5274
@ 17mm
C
113toll5 1B - 37
X\ '
C C
3,4-Cyclohexano-
[0,4,4]-bicyclodeca-
diene-3,(l,6)
<^Y^Y^\
73 to
CXXJ
74 11
Decahydrophen-
anthrene
^^
-18 to
274 to 275
0.993
1. 5335
^Xx^X^X
-20
@ 737mm
C}f
520
Name and Carbon Skeleton
M. P.,C.
B. P., C.
@ 760mm
DT
-B
Additional Data
Methyldecahydro-
phenanthrene
^\
76.5 "
f xX ^ Sv r >x r
XX'^X^
@ 1mm
l,4,5 ) 8-Di-(endo-
methylene)-tetradeca-
hydroanthracene
^TN^N^TN
157 to 159*
CiXJiJ
@ 16mm
Decahydroretene
^x.
336 to 340
0.975
1.51501 39
1 J
155 to 158"
0.9342 8B
1 1 1
@ 10mm
oo
1
1
c
521
Name and Carbon Skeleton
M.PSC.
n ~p o/-
/>, /'., C.
@ 760mm
DT
B
Additional Data
Hexadecahydro-
triphenylene
/\
186 to 188.5 M
0.95 18
f^^Y^^^r
^x^XjX^x
@ 12mm
Hexadecahydro-
chrysene
m
360 20
168 '
1.0129 3
1.5442 8
@17
t^^r^T^^
@ 0.5mm
1 II 1
154 3
@ 0.3mm
Cn-H.jn-8
a-Camphorene
c
1
c-c-c=c-c
r^
190 to 192 27
@ 12mm
178 to 180 80
@ 8.5mm
0.8864 "
0.8870
0.8844 w
1.4998"
1.50339 81
1.50199 "
V ?
177 to 178"
@ 6mm
i 1
178"
@4.5mm
522
Name and Carbon Skeleton
M. P., e C.
B. P., C.
@ 760mm
*
8
Additional Data
Sciadopitene
W5- + 11.05 *
c
95 to
<^V
c hO
96 24
r--~H^^
cc^
11 ^^
c-c-c
Isosciadopitene
l]g- +22.13 *
c
106 to
X^./
107 "
c JL^XJ
110 to
f^^^^r^^K
111 88
^^/^^
\
c-c-c
9, 10-Diisobutyldeca-
hydroanthracene
c-c-c
1
c
1
r/ X Y X ' X Y X ^ x i
86 to
87 22,23
145
@ 0.01mm
^^^^^^
1
c
1
c-o-c
S23
8
a
1/5
MS
S
1
u
*
a
524
Name and Carbon Skeleton
5. P., C.
@ 760mm
Additional Data
Pseudocholestene
C (C; 8
J y , +60.13
7 to
78
'8 to
79 9 > 19
CJEl2n-8
3-Methyl-A'(?)-
cholestene
C (C) 8
81 to
82 7
S2S
(1) K. Alder and G. Stein, Ber. 67, 613, 1934.
(2) H. Bode, Ber. 70, 1167, 1937.
(3) J. v. Braun and G. Irmisch, Ber. 65, 883, 1932,
(4) B. Charlampowiczowna and L. Marchlewski, Bull, intern acad. polon. 1930 A, 376.
(5) O. Diels and K. Alder, Ann. 460, 98, 1928.
(6) J. P. Eykman, Chem. Weekblad 4, 41, 1907.
(7) S. N. Fanner and G. A. R. Kon, J. Chem. Soc. 1937, 414.
(8) K. Fleischer and E. Retze, Ber. 55, 3280, 1922.
(9) I. M. Heilbron, R. A. Morton, and W. A. Sexton, J. Chem. Soc. 1928, 47.
(10) F. Hofmann and P. Damm, Kaiser- Wilhelm Soc. 2, 97, 1926.
(11) W. Huber, Ber. 71, 725, 1938,
(12) T. Ikeda, Sci. Papers Inst. Phys. Chem. Res. Tokyo, 7, 48, 1928.
(13) V. N. Ipatieff, W. Jackowlew, and L. Rakitin, J. Russ. Phys. Chem. Soc. 40, 494, 1908; Ber. 41,
996, 1908.
(14) K, Kofuku, Ozamada, and Nishi, J. Chem. Soc. Japan 54, 364, 1933.
(15) E'^Knoevenagel, J. prakt. Chem. [2] 97, 288, 1918.
(16) E. P. Kohler and J. Kable, J. Am. Chem. Soc. 57, 917, 1935.
(17) G. Kraeraer and A. Spilker, Ber. 29, 552, 1896.
(18) S. Lebedev and L. Mereshkowski, J. Russ. Phys. Chem. Soc. 45, 1363, 1913.
(19) H. Lettre", Z.<physiol. Chem. 221, 73, 1933.
(20) C. Liebermann and L. Spiegel, Ber. 22, 135, 1889.
(21) C. Liebermann and L. Spiegel, Ber, 22, 779, 1889.
(22) E. Martin, Ann. combustibles liquides, 12, 97, 1937.
(23) E. Martin and G. Hugel, Bull. soc. chim. [4] 53, 1500, 1933.
(24) K. Nishida and H. Uota, J. Agr. Chem. Soc. Japan 11, 489, 1935.
(25) J. Olsson, Ing. Vetenskaps Akad. Hand. 1931, No. Ill, p. 27.
(26) H. Roscoe, Ann. 232, 348, 1886.
(27) L. Ruzicka and M. Stoll, Helv. Chim. Acta 7, 271, 1924.
(28) W. Schrauth and K. Gorig, Ber. 56, 2024, 1923.
(29) J. Schmidt and R. Mezger, Ber. 40, 4240, 1907.
(30) F. W. Semmler and K. G. Jonas, Ber. 46, 1566, 1913.
(31) F. W. Semmler and I. Rosenberg, Ber. 46, 768, 1913.
(32) H. Staudinger, Ber. 59, 3019, 1926.
(33) H. Staudinger and H. Bruson, Ann. 447, 97, 1926.
(34) H. Staudinger and A. Rheiner, Helv. Chim. Acta 7, 23, 1924.
(35) H. E. Stavely and W. Bergmann, J. Org. Chem. 1, 575, 1937.
(36) H. Stobbe and F. Reuss, Ann. 391, 151, 1912.
(37) F. Tiemann and P. Krueger, Ber. 26, 2675, 1893.
(38) H. Uota, J. Dept. Agr. Kyushu Imp. Univ. 5, 117, 1937.
(39) A. J. Virtanen, Ber. 53, 1880, 1920.
(40) H. Wieland, Z. physiol. Chem. 142, 191, 1925.
(41) H. Wieland and F. Bergel, Ann. 446, 13, 1925.
(42) H. Wieland and V. Wiedersham, Z. physiol, Chem. 186, 229, 1930.
(43) R. Willstatter and M. Heidelberg, Ber. 46, 517, 1913.
(44) R. Willstatter and E. Waser, Ber. 44, 3423, 1911.,
526
Name and Carbon Skeleton
i/ p r
1\1. Z , t C-.
B. P., C>
760mm
D?
"8
Additional Data
Di-[f erf-butyl ethynyl]-
cyclohexylidene
methane
.I,.r\
105 to 110*
@3mm
0.8578*
1.4838 8
CCOs C <^J
c c
III
III
c
1
c-oc
1
"1
2-Methyl-S-iso-
*Structure taken from
propenyl-l-(2-methyl-
5-isopropenylcyclo-
hexen-2-yl)-cyclo-
Beilstein.
hexene-2
(Biscarvene*)
169 to 171
@ llmm
C C
/ \
o-o
/ \
r**~-f* o r*
u :=s t> v/ \*
1 1
C C
527
Name and Carbon Skeleton
M. P.,C
B. P., C.
@ 760mm
D?
B
yl dditional Data
l,2-Di-(2,2-dimethyl-
[1,2,2] < 3 .>-bicyclo-
heptylidene)-ethane
( Dicampheny lidene
ethane)
181 7
C C C
C rt H.2n-10
CTT
22 Al 34
1 ,4-Di-(2,2-dimethyl-
[1,2,2] < 3 - 6 >-bicyclo-
heptylidene)-butane
Ma- +67.30'
(1 ,4-Dicampheny lidene
butane)
210 7
@25mm
0.952 7
15
C C
/ c >=c-c-c-c=/ c \
C27 X144
Cholestadiene-2,4
[]-- 112.5
C C 8
798
W5-+114.0 "
f^^\^\
63 I0
OJ
<^^^^c^
61*
528
Name and Carbon Skeleton
If. P.,C.
5. P., C.
@ 760mm
HP
4
Additional Data
Choleetadiene-3,5
o]=- 103.24"
C Cs
rr>
dr
76 l
75.9 to
80 4
78 to
79
]- -63.75"
CJEljn-lO
Ctolestadiene-4,6
[]- +45.77"
rH
or
84 to
85 <
7-Dehydrocholestene
c
c (c) 4 ~oc
^vJx^X^/
88 to
89
(1) E. Bergmann and Y. Hirshberg, Nature 142, 1037, 1938.
(2) A. Butenandt and H. Kudsuss, Z. physiol. Chem. 2S3, Mil, 1938,
(3) K. Dimroth and G. Trautmann, Ber. 69, 66$, 1936.
(4) J, C. Eck, R, L. van Peursem, and E. W. Hollingsworth, J. Am. Chem. Soc. 61, 171, 1939.
(5) H. B. Gillespie and C. S. Marvel, J. Am. Chem, Soc. 52, 3368, 1930.
(6) C. Harries and P. Kaiser, Ber. 32, 1320, 1899,
(7) G, Langlois, Ann. cliim, [9] 12, 265, 1919.
(8) R. Schoenhimer and E. A, Evans, Jr., J. Biol. Chem. 114, 567, 1936.
(9) H. E. Stavely and W. Bergmann, J. Org. Chem. i, 567, 1937.
(10) H. B. Stavely and W. Bergraann, J. Org. Chem. 1, 575, 1937.
529
Name and Carbon Skeleton
^ 760mm
DT
w 20
Additional Data
[0,3 ,5]-Bicyclodeca-
pentaene
co
98.5 to
99 c
Tricyclopentadiene
r^TN^IN-^v
60 7 - 8 - 9
254 l
u c 1 c 1 >/
66 2
@ 766mm
^xjx^xlx^/
68
HO 7
@3mm
105 8
@ 3mm
90 to 92
@ 0.06mm
C 18X124
3-Cyclopentadien-2 ,4-
ylidene-l-(2,6,6-tri-
methylcyclohexen-1-
yl)-butene-l
(6-(/3-[2',6',6'-Trimethyl-
cy clohexen- 1 -y 1 ] -vinyl ) -
6-methylfulvene)
Illtoll3 4
@ 0.5mm
C
c c
ClXlf <
530
Name and Carbon Skeleton
M. P.,*C.
BP r*
. Jr, f U-.
@ 760mm
pr
s
Additional Data
3-Cyclopentadien-2,4-
ylidene-l-(2,6,6-tri-
methylcyclohexen-2-
yl)-butene-l
(6-(/J.[2%6' f 6'-Trimethyl.
107 to 109 4
cyclohexen-2-yl]-vinyI) -
6-methylfulvene)
@5mm
/\ c
c c
6,10-Dimethyl-2-cyclo-
pentadien-2,4-ylidene-
undecatriene-3,5,9
(6-[4* f 8'-Dimethylnona-
trienyM',3',71-6-methyl-
fulvene)
139 to 141 *
@ O.Smm
c-c-c>c-c^c-<>-c-c^c-c
XX. c c
u
Tetrahydrotetracyclo-
pentadiene
^TN^TN^T^
200 to
.CiXiXiX)
202
531
Name and Carbon Skeleton
M. P.,C,
3. P., C.
@ 760mm
DT
s
Additional Data
Dicyclohexen-1-yl-
butadiyne
/ \ - - ff \
\J sc - csc -\^_y
62.5 to
63*
Dihydirotetracyclo-
pentadiene
XTX^tN^1N-^\
205 3
361*
CiXiIiX)
@ 766mm
a-Tetradecahydro-
perylene-A-
r^N^
180 to
181.5 "
532
Name atkl Carbon Skckion
Af. P. t C.
B. P., C+
(a} 760mm
Iff
n%
Additional Data
/3-Tetradecahydro-
perylene-A-
3,4,9,10,9',10'
161 to
162 "
(1) K. Alder and G, Stein, Ann. 485, 223, 1931.
(2) K. Alder and G, Stein, Ann. 490, 204, 1932.
(3) K. Alder and G. Stein, Ber, 67, 613, 1934.
(4) E. Kohler and J. Kable, J. Am. Chem. Soc, 56, 2756, 1934.
(5) R. Kuhn and K. Walienfels, Ber. 71, 1889, 1938.
(6) PI. A. Plattner and A. St. Pfau, Helv. Chim. Acta 20, 224, 1937.
(7) H. Staudinger, Ber. 59, 3019, 1926.
(8) H. Staudinger and H. A, Bruson, Ann. 447, 97, 1926.
(9) H. Staudinger and A. Rheiner, Helv. Chim. Acta 7, 23, 1924.
(10) J. Thiele and H. Balhorn, Ann. 348, 1, 1906.
<11) S. Uqhida and S. Takata, J. Soc. Chem, Ind. Japan, Suppl. Binding 36, 222, 1933.
|
a s a
a o a
g
s
533
d
"8
,0
i I
nj O
*- !
*) (J C
"8 i
o^^
-t
i
o
o^o 6~o^uu -
I
w
Vftf Hf9
534
u
535
3
I
1
o
. 2 to 5 ^ - w g
J3iO*OiOe < OSr +aOO | 00
a- a- s ss s?
V
ou
II
536
I
ft*
oa
SCS)
^
^
i
i-o
A
i
\
te and Carbon Skel
<D Sr
J 1
o' cl)
*"
1
"1
:>o
5 ^ co
8 .2^:-
.
of o a
* ^
-
1^ "8
.
" *
j "1 1
^
eo
A: A;
XIX. HYDROCARBONS OF UNDETERMINED STRUCTURE
(Thought to belong to the naphthene or cyclic series)
539
C IS lit 4
Hydrocarbons of
Undetermined Structure
5Lf P / n
jxit r ., L<.
5. P., C.
@ 760mm
pr
<
Additional Data
Hexahydrogeijerene
96 @ 20mm *
0.8373 i
D* 6
1.4577 l
Hexahydroelemene
114toll6
@ 10mm
0.8450 <
1.4621
M.~-
Hexahydro-o-
curcumene
128 @ 7mm 2
0.8283 *
1.4952 2
@30
Hexahydro--
curcumene
128 @ 7mm*
0.8283 *
1.4552*
@30
-+"
d-Tetrahydroferulen
118 to 122
@10mm
0.8400
1, 45810
,.-,.
540
(1) A. R. Penfold and J. L. Simonsen, J. Proc. Roy. Soc. N. S. Wales, 66, 332, 1932.
(2) B. S. Rao and J. L. Simonsen, J, Chem. Soc. 1928, 2496.
(3) P. W. Semmler, K. G. Jonas, and P. Roenisch, Ber. 50, 1823, 1917.
(4) F. W. Semmler and P. Liao, Ber. 49, 794, 1916.
541
Hydrocarbons of
Undetermined Structure.
M. JVC.
B. P., C.
(' 760mm
^
S
Additional Data
C nil xn -2
Dihydrobicycloekasan-
talane
204
0.8705
1.47151
@ 768mm
@15
@ 15
75 to 77
@ 10mm
Tetrahydrogeijerene
95 @ 20mm *
0.85058 '
1.4695 1
@25
Decahydrochamazulene
119 to 120*
0.8808 2
1.4776*
@ 12mm
@ 15mm
@ 15mm
Decahydro-S-guaiazu-
lene
130 to 13 1 s
0.8798 2
1.4783*
@ 13mm
@15
15
132 to 134 2
0.8823 2
1.4790*
@ 12mm
@15
542
Hydrocarbons of
Undetermined Structure
M. P.,*C.
B, P,, C
760mm
Of
W >
Additional Data
CnMsn-2
Wg- +36.99"
Tetrahydroatractylene
129 to 130 "
0.9030 "
1.49589 '
@ 10mm
u-
12
Tetrahydrobetulene
W^-3 *
118 to 120 8
0.8737
1.4744 s
@ llmm
@18
018
Tetrahydrocaryophyl-
lene
M..-
122 to 123 10
0.8712 10
1.4700 10
@ 12mm
Tetrahydroelemene
[a] J) --15.2 >
118 to 120
0.8576
1.4760*
[] 1) --20.4
@ 12mm
0.8659
117 to 119
@ 10mm
Tetrahydroguaiene
Wi, - + 10.52
118 to 119"
0.8806
1.47840"
@7mm
0.8884
1,481 1 1
126 to 128
@1S
15
@12mm
543
CigHn
Hydrocarbons of
Undetermined Structure
M. P.,C
B. P., C.
760mm
*
S
Additional Data
C nH 2 ft -2
M-+5.6-
Tetrahydro-o-
santalane*
*Suggested by Si-
monsen, "The Ter-
c
115 to 116 l *
0.8655 ia
1. 46908
penes/' Vol. II, p. 548.
fTl^c c-c c c
@9mm
c c
Tetrahydrosantalene
W J5 -f7.5 OJ
116 to!18 7
0.864 7
1.4676 7
@9mm
Tetrahydroselinene
(a]-H.12 011
128 to 130 4
0.8881
1.4823*
@ 12mm
0.8889
1.48259
126 to 128"
@ 10.5mm
125 to 126 "
@ 10mm
0.8903 *
0.8910*
0.8970 *
1.4830 *
1.48375 "
1.4877 *
A fully hydrogenated
sesquiterpene
..,.,.
265"
0.8994
@22
544
Hydrocarbons of
Uudetenti Ined S tructure
M. /'.,"('.
B. P., C.
(f4 76()mm
tr?
,
Additional Data
Tetrahydrozingiberene
130 to 135 *
0.842 6
1.463 s
@ 18mm
@15
@15
(1) A. R. Penfold and J. L. Simonsen, J. Proc. Roy. Soc. N. S. Wales 66, 332, 1932.
(2) L. Ruzicka and A. J. Haagen-Smit, Helv. Chim. Acta 14, 1104, 1931.
(3) L, Ruzicka and A. J. Haagen-Smit, Helv. Chim. Acta 14, 1122, 1931.
(4) L. Ruzicka, D. R. Koolhaas, and A. H, Wind, Helv. Chim. Acta 14, 1171, 1931.
(5) L. Ruzicka and A. G. van Veen, Ann. 468, 143, 1929.
(6) P. W. Semmler, Ber. 41, 1488, 1908.
(7) P. W. Semmler, Ber. 43, 445, 19101
(8) P. W. Semmler, K. G. Jonas, and E. L. Richter, Ber. 51, 417, 1918.
(9) P. W. Semmler and F, Liao, Ber. 49, 794, 1916; 50, 1286, 1917.
(10) P. W. Semmler and E. Mayer, Ber. 45, 1384, 1912.
(11) P. W. Semmler and P, Risse, Ber. 45, 3301, 1912.
(12) P. W. Semmler and P. Risse, Ber. 46, 2303, 1913.
(13) A. Soltys, Monatsh, 53-54, 185, 1929.
(14> S. Takagi, J. Pharm. Soc, Japan No. 473, 1-10, 1921.
545
Hydrocarbons of
Undetermitied Structure
if p C
*U / . , V^
J3. P., C.
@ 760mm
Iff
*s
Additional Data
CnHan-4
Carveprene
183 to 186 9
Chamene
W^-H-35 "
168 to 170"
0.8228 ll
1.4686"
86 to 88 "
@25
@25
@ 50mm
Citronellal-terpene
0.8535 8
1.4875 8
Dacrydene
(a 1^.4. 14.48 27
165 to 166 27
0.8524 27
Z3 22
Isochamene
L 1/3
88 to 90 "
0.8222
1.4726"
@ 50mm
25
V to HH
546
Hydrocarbons of
Undetermined Structure
Af. P.,C.
R t> <*/"*
X. /*., C.
@ 760mm
D?
ng
Additional Data
Norbicycloekasantalane
[a]^-- 19
186 to 189"
0.8827 "
1.4779"
62 to 64 "
Bicycloekasantalane
183.5 "
0.871 I8
1. 46856 18
@ 767mm
0.885 18
1.4774 18
72 to 74 "
@ 10mm
57 to 59 "
Dihydroaromadendrene
121 to 122
0.9014
1.4871 3
@ 10mm
@17
547
C 16
Hydrocarbons of
Undetermined Structure
M.,.,C
B. P., C.
@ 760mm
Iff
s
Additional Data
CnHaa-4
Dihydrocopaene
[a]-12.2 M
118 to 121"
0.8926 8<
1. 47987 s *
@ 12mm
@18
temp.not
given
Dihydrocyperene
W- + 7.6-
113 to 116 ' 2
0.9332 12
@ 12mm
D 19
Dihydroguaiene
[<].-- 26.65
124 to 125 16
0.89 14 7
1.4836 30
@ 15mm
25
23
122 llmm 7
0.8955 1B
1. 4981 7 7
102.2 30
0.9089 7
@ 20.2
@ 1mm
1.4894 16
Dihydro-a-gurjunene
[a^^^igow
129 29
0.9090 29
1. 49061 29
0.8977 29
1.4897 2
ii XI 14
548
Hydrocarbons of
Undetermined Structure
B. P., C.
() 760mm
tit
i/J
Additional Data
Dihydro-0-gurjunene
W. 42-
120@8mm 19
0.9239
l. 49490
[.^--37.5
115 to 117 23
0.9172 29
1.4922 29
@ 7mm
Dihydroledene
112 tollS 13
0.9075 18
1. 492324 13
@ 6mm
Dihydro-a-santalene
0.899 "
1.495 19
Dihydroselinene
138 to 139 "
0.8992 "
1.4878"
12mm
24
549
Hydrocarbons of
Undetermined Structure
AT. P.,C.
B. P., C.
@ 760mm
Of
s
Additional Data
CnH-Jn-4
Dihydrosesqui-
citronellene
13Uol33 22
0.83 16
1.4800"
@ 12mm
Dihydrovetivene
H>~1.8 21
126 to 132"
0.90734 2
1.48685"
Elemane
115 to 119 10
0.8830 10
1.4950 10
@ 10mm
17
@17
Ferulene
[]g-+6
126 to 128"
0.8687 20
1.4837 7 =0
@ 10mm
0.8698 20
1. 48423 20
124 to 126
@ 7mm
Isodihydro-
caryophyllene
[a] --29.4
137 to 138 17
0.8872
1.4880*
@ 19mm
@21
@21
124 to 124.5 '
0.919 "
1.4925"
@ 12.75mm
550
Hydrocarbons of
Undetermined Structure
ji/f P *r
M.* Jr., Ix.
B. P., C
@ 760mm
/*
n$
Additional Data
Octahydroazulene
123 to 124.5 14
0.8935 26
1.490
@ 10mm
@25
1.4921 l <
0.8967 M
15
Tetrahydrokessylene
105 to 108 >
0.8931 l
1.47289
@ 5mm
o-Kayene
H 7.9'
33.5 to 34.5 31
0.8600
1.47 13
@8mm
/5-Kayene
WJ 1S.1-
44.5 to 45.5 8l
0.8591
1.4721 8l
@8mm
CifH.it
Dihydroabietene
0.933
1.522
551
Hydrocarbons of
Undetermined Structure
M. P.,C,
B. P., C.
@ 760mm
DP
B
Additional Data
CftHftn-4
Tetrahydroditerpene
26*
Tetrahydromaaoene
141 to 142
0.9158
1.5030"
@ 0.2mm
Totarene
74,5 to
75 2
76
Eicosahydrocarotene
11". +0.337^
206 2B
0.8748 M
1.4821
@ 0.000 1mm
@ 24.2
24.2
552
(1) Y. Asahma and S. Nakanishi, J. pharm. Soc. Japan 48, 1, 1928.
(2) 0. Aschan, Ann. 461, 1, 1928.
(3) L. H. Briggs and W. F. Short, J. Chem. Soc. 1928, 2524.
(4) M. S. Carrie, J. Soc. Chem. Ind., 51, 367T, 1932.
(5) E. Deussen and K. Meyer, J. prakt. Chem. [2J 90, 318, 1914.
(6) T. Easterfield and G. Bagley, J. Chem. Soc. 85, 1238, 1904.
(7) A. L. Gandurin, Ber. 41, 4359, 1908.
(8) R. Horiuchi, Mem. Coll. Sci. Kyoto, Imp. Univ. Ser. A. 11, No. 3, 171, 1928.
(9) J. R. Hosking and C. W. Brandt, Ber. 68, 13 11, 1935.
(10) H. Jansch and P. Fantl, Ber. 56, 1363, 1923.
(11) K. Kafuku, T. Nozoe, and C. Hata, Bull. Chem. Soc. Japan 6, 40, 1931.
(12) Y. Kimura and M. Ohtani, J. pharm. Soc. Japan 48, 128, 1928.
(13) G. Komppa, Kgl. Norske Videnskab. Silskabs, Skrifter, 1933, 1-16.
(14) S. Ruhemann and K. Levy, Ber. 60, 2459, 1927.
(15) L. Ruzicka and E. Rudolph, Helv. Chim. Acta 9, 118, 1925.
(16) L. Ruzicka, A. H. Wind, and D. R. Koolhaas, Helv. Chira. Acta 14, 1132, 1931.
(17) F. W. Semmler, Ber. 36, 1038, 1903.
(18) "F. W. Semmler and K. Bode, Ber. 40, 1124, 1907.
(19) F. W. Semmler and W. Jakubowicz, Ber. 37, 1141, 1914.
(20) F. W. Semmler, K. G. Jonas, and P. Roenisch, Ber. 50, 1823, 1917.
(21) F. W. Semmler, F. Risse and F. Schr6ter, Ber. 45, 2347, 1912.
(22) F. W. Semmler and K. E. Spornitz, Ber. 46, 4025, 1913.
(23) F. W. Semmler and K. E. Spornitz, Ber. 47, 1029, 1914.
(24) F. W. Semmler and H. Stenzel, Ber. 47, 2555, 1914.
(25) A. E. Sherndal, J. Am. Chem. Soc. 37, 1537, 1915.
(26) W. F. Short and H. Stromberg, J. Chem. Soc. 1937, 516.
(27) H. G. Smith, J. Soc. Chem. Ind. 30, 1353, 1911.
(28) J. H. C. Smith, J. Biol. Chem. 90, 597, 1931.
(29) W. Treibs, Ber. 68, 1751, 1935.
(30) V. M. Trikojus and D. E. White, J. Proc. Roy. Soc. N. S. Wales 68, 177, 1935.
(31) R. Worsley, Bull. Imp. Inst. 32, 253, 1934.
553
Hydrocarbons of
Undetermined Structure
M.
CnH.2n-.ft
Cyclooctatriene
/>-Menthatriene
Methylmenthatriene
B. P., C.
to
SO
@ 760mm
D,
s
.147.2 to
0.9086 122
1. 52844 12
148.2 122
0.903 12
133 to 135 m
0.91 2 131
@ 7 15mm
<}0
57 to 57i5 21
0.925
(}4<>to
@o
50mm
36 to 40 121
( A 13mm
31.2 to 3 1.8 2
@, 8mm
183 m
0.863 U3
1. 49693 113
90 to 91.5 i
0.8728
1.5007 89
@21mm
0.8745 68
1. 50152 8
89.2 to 89.4 '
0.8747
1.501241
@ 18mm
0.8748 68
19.0
74 to 75
0.8738
1. 49875 '
@ 10mm
@ 19.0
18.8
74 to 76 M
0.8686 1
@9.5mm
18.8
0.8776 60
15
Additional Data
= +90.32
5S4
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
@ 760mm
Iff
8
Additional Data
Geijerene
85@17mm w
0.8720 *
1.4888 6 *
1 ,4-Diisopropenyl-
cyclohexene-1
or
l-Isopropenyl-4-iso-
pfopylidene-cyclo-
hexene-1
Low boiling
95 to 98 *
0.8715*
1.48717 4
@20mm
n a
1.50902*
n*
7
High boiling
105 to 108 *
0.8706 *
1.48650*
@20mm
W S
a
Aromadendrene
K 2 ?? 38 "" 6 - 109
121 to 121.4*
0.9116*
1.4978*
<> 10mm
0.9157 *
1.4993 *
121 10mm*
@17
555
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
760mm
Dl>
B
Additional Data
CflHjn-l
Atractylene
Mg- +78.35 *
260 to 263 27
0.9101
1.50893 *
125 to 126 27
D\l
1.51795 *
@10mm
0.9154 w
@ 13
1 08 to 109 1W
D\l
@3mm
0.9 189 IM
13
Azulene terpene
[oJ J> -+lL40
30 to 31 3
167 to 168.4
0.98771 ftl
1.5021 78
@ llmm
@25
127 to 128"
0.98465 61
@10mm
n"
^26
120 to 122"
@10mm
0.9835 w
140 to 1 45 88
@5mm
0.9134 78
117 to 120 r *
@5mm
135.6"
Betulene
[08- +6-
123 to 127 M
0.9120"
1.4952"
@ 13mm
@21
@21
130 to 132 ^^
(fy 2QCOJCQ
0.9213 "
1.5144 1W
556
Hydrocarbons of
Undetermined Structure
X.P..-C.
B. P., C.
@ 760mm
DT
<
Additional Data
/"* TT
VcsnJt-Lgnfl
Bulnesene
113.5 toll5" u
0.9149 119
1. 50467 llf
(a) 6mm
Calamene
lal^+5-
127 to 130"
0.9224 " 7
1.50572"
@>, 14mm
D 20
1.5023 74
123 to 126 97
0.9231 74
@ 19
@ 10.5mm
D\l
Camarene
||=-f6.74
263 42
0.9056
1.500
121 to 122 42
@30
(a) 30
(a) 4mm
Carlinene
139 to 141
0.8733
1.492"
@20mm
@ 23.8
@ 23.8
557
llydr ocarb OTIS of
[ hi delertn in ed Slrm tt<ic
M. /vr.
1
Iff
"L-
Aildilionnl Ditto
a-Caryophyllene
W--4.97-
130 to 131 62
0.8923 62
1.4942* 2
!] -24.07 1G
<$ 24mm
Dll
25
|]2--26.174 0|;
139 to 140 l5
8953
1.49617
@19mm
0.8959 18
1.49665 17
lJ/>"
125 to 125.5 17
14.5mm
123 to 124 17
@ 14.5mm
0.8986 19
0.8990 17
0.89951
@19
1.496 19
(0)18
1.496 19
iU--29r"
122 to 124 ie
/>n
@ 16
@ 12mm
0.8965 l
131 @ 10mm 19
@ ISnim
558
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
@ 760mm
Iff
"8
Additional Data
Cedrene
MD--85.5 "
264 to
0.9325
1.49798"
[^..gS-ii
268 "M"
0.93258
1.49817 "
264 "
0.9338"
1.5015"
[al^^-82 0107
263.5 to 264
0.9342 "
1.50251
[a] -67 lw
261 to 262 ls - u
0.9345 M
1.5028"
D
237 M
0.9359 "."
1.50233 8J ^
[al^^-60.8 0103
262 to 263
0.9362 1OT
@15
@ 750mm
0.9365 IW
1.4991 18
[al^^-60 012 ' 98 - 107
129tol32 !W
@17mm
124 to 1 26
@12mm
123 to 124"
@12mm
118 to 1 19
0.9385 1W
0.9231
0.9354 "
@15
0.9366
15
1.4964"
W U
1.5011"
1.5133"
M --59"
MD- -56.51 '
131 to 132 7
0.9367 "
"ft
[a] =~47.8 0fi7
@ 10mm
@15
1.5258"
D
119 M
n *H y
[ a ] D = -47.54 M
@ 10mm
116 to 117 "
@10mm
114 to 115"
112 to 1 13 H
119 to 121"
559
Culls 4
Hydrocarbons of
Undetermined Structure
M p r
Ml - V* .
B. P., C.
@ 760mm
DP
-B
Additional Data
Clovene
Fraction I
25 1 to 253 72
0.9215
1.4968
[a] D -- 29.66 w
@ 765mm
@18
@18
117 to 119
@ 16mm
Fraction II
260 to 262 7 *
0.9244
1.4951
[ak .- 39,66
@ 765mm
@18
@18
122 to 124"
@ 16mm
261 to 263 u <
0.924 *
1.4980"
Wp-+U
131 to 139"
0.92223 I7
1.4740 "
@ 15. 5mm
JT)J9
19
[a]-fl.3
111 to 113"
0.930 1U
1. 50066 " 4
@ 10mm
^18
a-Costene
[.] 12-
122 to 126
0,9014"
1.49807
@ 12mm
@21
O16
/3-Costene
H.-+-
144 to 149 M
0.8728 M
1.4905"
@ 18mm
@22
Cubebene
[] D - -39.15
255 to 260 M
0.915 M
220 M
@15
Hydrocarbons of
I Undetermined Struct u re
M. /V'f.
B. P., C.
("' 760rnni
DT
'*/?
Additional Data
tt-Curcumene
MK=-22.9
128 to 130 s
0.8633 63
J .4944 M
@ 9mm
/?S
@30
-Curcumene
[ Q! ]3o == _27.9 063
128 to 130 3
0.88 10 63
1.4940 63
@ 6mm
/?S
@30
Curcumene
[a]g=+ 16.35
139 to 142
0.9235
1.50594"
@ 13mm
@24
@24
140 to 142
12mm
Cyclolinaloolene
165 to 167 88
0.81 12 s
1.4602
Cyclosesquicitronellene
129 to 132
0.8892 98
1.5069"
@ 15mm
561
Hydrocarbons of
Undetermined Structure
K/r p o/^
JXL Jr., i/.
B. P. t C.
@ 760mm
if!
"S
Additional Data
Cyperene
Wg-+i.s-
110 tollS 48
0.9372 49
1.50127
@ 7mm
DS
13
a-Cyperene
132 to 133 7
@ 15mm
Dicyclic sesquiterpene
[.]- U.9-
115 to 117 3
0.8932 63
1.4936 W
@ 7mm
rv30
^30
@30
Dysoxylonene
136 to 137 M
0.9236 "
1.5063"
@ 10mm
@15
Elemene
115 to 117 92
0.8797
@ 10mm
562
Hydrocarbons of
Undetermined Structure
M. P.,C.
11. P., C.
(ft, 760mm
D?
W S
Additional Data
C n H. 2 n-6
Equinopanocene
[]{, +33.5
135 to 138 46
0.9051 46
1.5013 4e
@ 15mm
@5
@15
Fokienene
[]>;= + 16.93
112 to 114 31
0.8802 31
1. 49594 81
@ 7mm
15
@13
Galipene
255 to 260 "
0.912 "
@19
Gonystylene
Wg=+40 M
137 to 139 23
0.9183 23
1.5134"
@ 17mm
@17
@15
563
Clftl24
Hydrocarbons oj
Undetermined Siructm c
/. P.,C.
B. P., C.
(rft 760mm
7)f
S
Additional Data
CJElzn-G
Guaiene
a] D =-l6.S"
135 to 138 36
0.8954 28
1. 49468 28
[a]g=- 40.35 27
@ 14mm
@25
@25
134 to 136 3
0.9085 27
1.5022 75
[]- -66.11
@22mm
0.9182 3B
1.50114 ue
128 to 130 78
0.910
1.50049 27
@ 12mm
0.9115 75
124 28
@19
@ llmm
0.9133 28
123 to 124 27
@0
@> 9mm
124tol28 llfl
@ 13mm
a-Gurjunene
[aj.-95'w
114 to 116 "
0.919 1M
1.5010 90
[a] z> --90 7a
@ 10mm
0.918 M
1.501 l08
122 to 126 7B
0.9285 76
1.5047 76
@12mm
@15
@15
119 18
@ 12mm
iso-a-Gurjunene
[]-- 135
0.9109 108
1.5101 108
CltXlfl4
564
Hydrocarbons of
Undetermined Structure
M. P.,C
B, P., C.
@ 760mm
iff
<
Additional Data
/3-Gurjunene
W X) a =-f74.5 ow
120 to 123 M
0.9348 90
1. 50526
[ a ] fiSS -{.70.5
@ 13mm
0.9329 M
1. 50275 M
122.5 to
0.9321 108
1.5022 108
123.5 18
@ 12mm
113.5 to
114
@ 7mm
iso-/3-Gurjunene
[^36
0.9313 IM
1.5109 1M
Hexahydro-
chamazulene
118 to 124 7
0.911 7 7
1.5200 76
@ llmm
Humulene
[-8 as-
263 to 266 u
0.8977 "
1.5021 ll
132 to 137
n 20
^20
@19
@ 13mm
0.9001 ll
1.4978 11
D 15
8
a
565
Hydrocarbons of
Undetermined Structure
M. JP.,C.
B. P., C.
@ 760mm
Iff
-s
Additional Data
Isocamerene
MS- -11.21'
253
0.8942 2
1.4925 42
110 to 111 28
30
30
@ 5mm
Isoclovene
[a]g S6.6-
130 to 131 30
0.943 3fl
1.5039*
@ 12mm
19
19
Isocostene
W.-+S1-
130 to 135 88
0.9062 88
1. 50246 M
@ 12mm
21
Isofokienene
[-5- +3.92-
Fraction I
95 to 96 32
0.9075
1.5041 32
@3mm
@21
a-Isosantalene
H.-+W-
225 to 256 33
566
Hydrocarbons of
Undetermined Structure
M. JVC
B. P. t C.
@ 760mm
iff
H D
Additional Data
0-Isosantalene
lag- +16.89'
259 to 260
Isosesquichamene
^ 852i"
265 to 268 m
129 to
0.9320 *.i
@21.5
1.5109**." 1
@21.5
W--15.7 " 1
[]].=- 8.532 w
131 43,44,111
0.9367 " l
1.5009" 1
@ 12mm
Machilene
la] =+63"
142 to 144 73
0.9267 73
1.5104 M
@20mm
15
@15
Patchoulene
fa]g= -38.08 27
255 to 256 81
0.939 11<J
1.49835"
[]^= -42.10 51
254 to 256 > 16
252 to 255 52
@23
0.9296 27
1. 50094 "
[a]^* -36.52"
@ 743mm
0.9334 8l
112 to 115 27
@15
@ 12 to
0.93 7 62
12.5mm
@ 13.5
0.946 62
567
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
@ 760mm
D?
s
Additional Data
Populene
la]^- +21.22 M
121 to 122 54
@ 8mm
0.9135 M
1.504 64
7-Santalene
118 to 120 87
@9 to
10mm
0.9355 8 '
1.5042 87
Sesquibenhene
WS-+3S.7-
127 to 131 41
0.9162 41
1.5058 41
@24
Sesquichamene
lag- 89.85 43 ' 44
112.5 to
123.5 43 - 44
@ 12mm
0.9277 43 ' 44
1.5021 43 - 44
Sesquicitronellin
la]^* 4-0.36 M
138 to 140 "
0,8489 w
1.53252 M
568
Hydrocarbons of
Undetermined Structure
M. P.?C.
B. P., C.
@ 760mm
Iff
g
Additional Data
CftHtfi.fi
Sesquiterpene-1
140 la
0.902
@ 26mm
@15
Sesquiterpene-2
Mj>-+so*
153 to 154 18 "
0.9247 "*
@ 26mm
@15
Sesquiterpene from
aliharz oil
W^-H-iai.QQ "
270.8 to 271 83
0.9190 83
1.52252"
@ 754mm
@15
@15
Sesquiterpene from
balsoharz balsam
Wg 1-116.4
118 to 119 2
0.9104 2
1.4956 2
@ 8mm
@30
@30
Sesquiterpene from
caiyophyllene-dihydro-
chloride
[]- -35.39 JW
0.9191 1M
1.49901 lw
569
Hydrocarbons of
Undetermined Structure
AT. P.,C.
B. P., C.
@ 760mm
*
ng
Additional Data
Sesquiterpene from
citronellol
272 to 275 *
0.8643 80
170 to 172 80
@ 15
@ 16mm
157 80
@ 15mm
Sesquiterpene from
Ethereal Oil of Pittos-
porum
263 to 264
0.9100 6l
1.5030"
167 to 171
D\l
@60mm
Sesquiterpene from
alcohol from Capaiba
[a] D =* 61.7 m
balsam
252 2
0.952 " 2
1.5189 l
@ 759mm
15
570
Hydrocarbons of
Undetermined Structure
M. P., 9 C.
B. P., C.
@ 760mm
Iff
ng
Additional Data
CnH 2n -6
Sesquiterpene from
Matico Oil
1"]^=- 10.83 1M
138 to 139 10
@17mm
133tol34>
@ llmm
0.914 1M
0.916 10<J
1.50542 106
1. 50808 lw
a
1.52177 1M
w 21
1.53028 w
7
Sesquiterpene
from Ysop Oil
125 75
@ 12mm
0.91 16 76
@17
1.5012 75
Sesquiterpene
from Cubebene Oil
274 to 275 116
0.918 ll5
1.50467 115
Sesquiterpene from
Eucalyptus Globulus Oil
124 to 127"
@ 12mm
0.9078 75
1.4969 75
571
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
' @ 760mm
Iff
*g
Additional Data
C n H. 2n _ 6
Sesquiterpene from
Eucalyptus Globus Oil
127 to 131"
0.9172"
1.5001
@12mm
Sesquiterpene
266 26
0.9269 2
1.5094*
@30
30
Sesquiterpene
Ma- +58.40
265.5 to 266 101
0.9326 1
1. 50602 lw
@ 750mm
@15
Sesquiterpene
Mj,-- 55.48
247 to 248 "i
0.8956 101
1. 49287
@ 748mm
@15
Sesquiterpene
from Cymbopogon
Sennaarensis, Chiov Oil
%
Mg aa + 24.40
150 to 155 6
0.9114 M
@ 27mm
n 16
^15
Sesquiterpene
MS- + 16.1 M
127
0.8961
1.4990 M
@ 14mm
@30
30
572
Hydrocarbons of
Undetermined Structure
M. JVC.
B. P., C.
@ 760mm
P!
"S
Additional Data
CnHsn-e
Sesquiterpene
122 to 127 3
1.527
@ 10mm
@17
Terebenthene
[a] B -+3.2
155.4 to
0.8685 22
1.4648"
[] c --40.3 e
155.8 10
@25
@15
@ 748.9mm
0.867
@17
Vetivene
M B =- 10.20
Bicyclic
137 to 140 M
0.9321 96
1. 51 896 w
@ 16mm
0.9339 71
1.5179"
132 to 133 71
@15
@ 12mm
Vetivene
Tricyclic
123 to 130 w
0.9335 M
1.51126 w
@ 16mm
0.9372 71
1.5143"
126 to 127 71
15
15
@ 12mm
573
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
@ 760mm
Iff
ng
Additional Data
Dihydrocyclosclarene
M^+33.4 "
122 to 128 40
@ 0.15mm
0.9288 40
@25
1.5075 40
@25
0.9296 40
Dihydroisomanoene
123 to 124 "
@ 0.2mm
0.9164
19
@19
a-Dihydromanoene
149 to 150 38
@ 0.3mm
0.9206 "
21
1.5089"
a-Dihydropodocarprene
Mg-- 15.85"
83 to
84 8
/3-Dihydropodocarprene
[*] D -+1M**
203 to 204 '
@ 17mm
1.5121"
o-Dihydrophyllocladene
[]g- +23.25 8
73 to
/3-Dihydrophyllocladene
55
574
Hydrocarbons of
Undetermined Structure
M. P. t C.
B. P., C.
@ 7 60m m
Iff
S
Additional Data
Kaurene
86 to
0.9282 37
1.4912
3737
@106
@100
0.9330 87
@100
Allo-a-ergostane
W = + 170
84 to
85 4
Bombisestane
Wg-+18.6-
79 48
81
Cholestane
[a] c = +24.59
79110
71 104
70 to
71
575
Hydrocarbons of
Undetermined Structure
M. l\ t C.
T? p r
n. /-,, o,
(ft) 760n)iii
iff
n ff
Additional Dttta
Lupane
184 to
185 20
Soja-7-sitostane
Wg-+.a-
87 6
"* XT
^28*1>
Pseudoergostane
W--+25J-
(5424
Ergostane
WjJ+22.9"
81 to
82
82 21
Artostane
101 65
576
Hydrocarbons of
Undetermined Structure
M.
B. P., C.
@ 760mm
DT
Additional Data
Stigmastane
84 to
84.5 ]
577
(1) K. v. Auwers and P. Eisenlohr, Ber. 43, 827, 1910.
(2) R. F. Bacon, PhilHpine J. Sci. 4A, 93, 1909.
(3) K. Birrell, J. Am. Chem. Soc. 57, 893, 1935.
(4) M. T. Bogert and C. P. Harris, J. Am. Chem. Soc. 41, 1676, 1919.
(5) K. Bonstedt, Z. physiol. Chem. 176, 269, 1928.
(6) A. T. Bose and W. Doran, J. Chem. Soc. 1929, 2244.
(7) A. E. Bradfield, B. H. Hegde, B. S. Rao, J. L. Simonsen, and A. E. Gillam, J. Chem. Soc. 1936, 667.
(8) L. Briggs, J. Soc. Chem. Ind. 56T, 137, 1937.
(9) L. H. Briggs and W. F, Short, J. Chem. Soc. 1928, 2524.
(10) J. Bruhl, Ber. 25, 142, 1892.
(11) A. Chapman, J. Chem. Soc. 67, 54, 1895.
(12) A. Chapman and E. Burgess, Proc. Chem.' Soc. 12, 140, 1896.
(13) E. Deussen, Ann. 359, 273, 1927.
(13a) E. Deussen, Ann. 388, 136, 1912.
(14) E. Deussen, Arch. Pharm. 240, 288, 1902.
(15) E. Deussen, J. prakt. Chem. [2] 114, 63, 1926.
(16) E. Deussen, J. prakt. Chem. [2] 145, 31, 1936.
(17) E. Deussen and A. Lewinsohn, Ann. 359, 245, 1908.
(18) E. Deussen and H. Philipp, Ann. 374, 105, 1910.
(19) E. Deussen, F. Weiss, P. Hacker, and P. Hille, J. prakt. Chem. [2] 117, 273, 1927.
(20) H. Dieterle and A. Salomon, Arch. Pharm. 270, 495, 1932.
(21) J. L. Dunn, I. M. Heilbron, R. F. Phipers, K. M. Samont, and F. S. Spring, J. Chem. Soc.
1934, 1576.
(22) G. Dupont, Ann. chim. [10] 1, 184, 1924.
(23) P. A. A. F. Eyken, Rec. trav. chim. 25, 44, 1906.
(24) E. Fernholz, Ber. 69, 1792, 1936.
(25) F. Fichter and J. Kate, Ber. 32, 3183, 1899.
(26) Y, Fujita, J. Chem. Soc. Japan 55, 6, 1934.
(27) J, Gadamer and T. Amenomiya, Arch. Pharm. 241, 22, 1903.
(28) A. L. Gandurin, Ber. 41, 4359, 1908.
(29) J. Gladstone, J. Chem. Soc. 45, 241, 1884.
(30) J. Gladstone, J. Chem. Soc. 59, 290, 1891.
(31) E. Glichitch, Compt. rend. 191, 1457, 1930.
(32) E. Glichitch, Parfums de France 8, 157, 1920.
(33) M. Guerbet, Compt. rend. 130, 1324, 1900.
(34) A. Guttenberg, Z. gas. exp. Med. 54, 642, 1927.
(35) H. Haensel, Geschaftsberichte, April-Sept., 1908.
(36) J. A. R. Henderson, R. O. O. McCrone, and G. J. Robertson, J. Chem. Soc. 1929, 1368.
(37) J. Hosking, Rec. trav. chim, 49, 1036, 1930.
(38) J. Hosking and C. Brandt, Ber. 68, 37, 1935.
(39) V. N. Ipatieff and V. Petrov, Ber. 60, 753, 1927.
(40) M. M. Janot, Ann. chim. [10] 17, 5, 1932.
(41) K. Kafuku and K. Ichikawa, J. Chem. Soc. Japan 54, 1011, 1933.
(42) K. Kafuku, T. Ikeda, and C. Hata, J. Chem. Soc. Japan 56, 1186, 1935.
(43) K. Kafuku and T. Nozoe, Bull. Chem. Soc. Japan 6, 111, 1931.
(44) K. Kafuku and T. Nozoe, Chem. News 143, 21, 1931.
(45) T. Kariyone and Y. Matsushima, J. Pharm. Soc. Japan, No. 546, 674, 1927.
(46) T. Kariyone and Morotomi, J. Pharm. Soc. Japan, No. 546, 671, 1927.
(47) C. Kawasaki, J. Phann. Soc. Japan 57, 736, 1937.
(48) K. Kawasaki, J. Pharm. Soc. Japan 55, 758, 1935.
(49) Y. Kimura and M. Ohtoni, J. Pharm. Soc. Japan 48, 128, 1928.
(50) A. Klages, Ber. 40, 2360, 1907.
(51) R. E. Kremers, J. Am. Chem. Soc. 45, 717, 1923.
578
(52) E. Montgolfier, Compt. rend. 84, 90, 1877.
(53) K. Moudgill and P, Virdhaehalam, Perfumery ami Essential Oil Record 13, 173, 1922.
(54) N. Nakao, J. Pharm. Soc. Japan, No. 513, 4, 1924.
(55) M. C. Nath, Z. physiol. Chem. 247, 9, 1937.
(56) K. Nishida and H. Uota, Bull. Agricult. Chem. Soc. Japan 7, 1, 1931.
(57) V. Pavesi, Rend. Inst. Lombardo [2] 37, 487, 1904.
(58) A. R. Penfold, J. Proc, Roy. Soc. N. S. Wales 61, 337, 1928.
(59) A. R. Penfold and J. L. Simonsen, J. Proc. Roy. Soc. N. S. Wales 66, 332, 1932.
(60) P. S. Pinkney and C. S. Marvel, J. Am. Chem. Soc. 59, 2669, 1937.
(61) P. B. Power and F. Tutin, J. Chem. Soc. 89, 1083, 1906.
(62) G. R. Ramage and J. L. Simonsen, J. Chem. Soc. 1938, 1208.
(63) B. S. Rao and J. L. Simonsen, J. Chem. Soc. 1928, 2496.
(64) P. Reindel and E. Walter, Ann. 460, 212, 1928.
(65) A. Reychler, Bull. soc. chim. [3] 15, 366, 1896.
(66) K. Roberts, J. Chem. Soc. 107, 1465, 1915.
(67) L. Rousset, Bull. soc. chim. [3] 17, 485, 1897.
(68) H. Rupe and F. Emmerich, Ber. 41, 1393, 1908.
(69). H. Rupe and K. Liechtenhan, Ber. 39, 1119, 1906.
(70) L. Ruzicka, Helv. Chim. Acta 6, 483, 1923.
(71) L. Ruzicka, E. Capato, and H. W. Huyser, Rec. trav. chim. 47, 370, 1928.
(72) L. Ruzicka and D. T. Gibson, Helv. Chim. Acta 14, 570, 1931.
(73) L. Ruzicka, D. R. Koolhaas, and A. H. Wind, Helv. Chim. Acta 14, 1178, 1931,
(74) L. Ruzicka, J. Meyer, and M. Mingazzini, Helv. Chim. Acta 5, 345, 1922.
(75) L. Ruzicka, S. Pontalti, and F. Balas, Helv. Chim. Acta 6, 855, 1923.
(76) L. Ruzicka and E. Rudolph, Helv. Chim. Acta 9, 118, 1926.
(77) L. Ruzicka and J. A. van Melsen, Helv. Chim. Acta 14, 397, 1931.
(78) S. Sabetay and H. Sabetay, Compt. rend. 199, 313, 1934.
(79) A. St. Pfau and P. A. Plattner, Helv. Chim. Acta 19, 858, 1936.
(80) Schimmel and Co., Geschaftsberichte, Oct. 1899.
(81) Schimmel and Co., Geschaftsberichte, Apr. 1904, 75.
(82) Schimmel and Co., Geschaftsberichte, Oct., 1909.
(83) Schimmel and Co., Geschaftsberichte, Oct., 1908, 80.
(84) O. Schreiner and E. Kremers, Pharm. Arch. 2, 273, 1899.
(85) F. W. Semmler, Ber. 27, 2520, 1894.
(86) F. W. Semmler, Ber. 39, 726, 1906.
(87) F. W. Semmler and K. Bode, Ber. 40, 1124, 1907.
(88) F, W. Semmler and J. Feldstein, Ber. 47, 2687, 1914.
(89) F. W. Semmler and A. Hoffmann, Ber. 40, 3521, 1907.
(90) F. W. Semmler and W. Jakubowricz, Ber. 47, 1141, 1914.
(91) F. W. Semmler, K. G. Jonas, and W. Richter, Ber. 51, 417, 1918.
(92) F. W. Semmler and F. Liao, Ber. 49, 794, 1916.
(93) F. W. Semmler and E. Mayer, Ber. 45, 1384, 1912.
(94) F. W. Semmler and F. Risse, Ber. 45, 355, 1912.
(95) F. W. Semmler, F. Risse, and H. SchrStter, Ber. 45, 2347, 1912.
(96) F. W. Semmler and K. E. Spornitz, Ber. 45, 1553, 1912.
(97) F. W. Semmler and K. E. Spornitz, Ber. 46, 3700, 1913.
(98) F. W. Semmler and K. E. Spornitz, Ber. 46, 4025, 1913.
(99) F. W. Semmler and K. E. Spornitz, Ber. 47, 1029, 1914.
(100) F. W. Semmler and H. Stenzel, Ber. 47, 2555, 1914.
(101) F. W. Semmler and E. Tobias, Ber. 46, 2026, 1913.
(102) "The Sesquiterpenes" [Milwaukee, 1904], 71, 108.
(103) H. v. Soden and W. Rojahn, Ber. 37, 3353, 1907.
(104) W. Steinkopf, H. Wmternitz, W. Roederer, and O. Wolynski, J. prakt. Chem. [2] 100, 65, 1920.
579
(105) S. Takagi, J. Pharm. Soc. Japan, No. 473, 1, 1921.
(106) H. Thorns, Arch. Phartn. 247, 591, 1909.
(107) W. Treibs, Bcr. 68, 1047, 1935.
(108) W. Treibs, Ber. 68, 1751, 1935.
(109) W. Treibs, Ber. 69, 41, 1936.
(110) L. Tschugaeff and W. Fomin, Ann. 375, 288, 1910.
(111) S. Uchida, J. Soc. Chem. Jnd. Japan 19, 611, 1916.
(112) L. Van Itaffie and C. Nieuwland, Pharm. Weekblad 43, 389/1906.
(113) O. Wallach, Ann. 264, 1, 1891.
(114) O. Wallach, Ann. 271, 285, 1892.
(115) 0. Wallach and E. Conrady, Ann. 252, 141, 1889.
(116) O. Wallach and P. Tuttle, Ann. 279, 391, 1894.
(117) P. Walter, Ann. 39, 247, 1841.
(118) P. Walter, Ann. chim. [3] 1, 498, 1841.
(119) H. Weinhaus and Scholz, Ber. Schimmel and Co., 1929, 269.
(120) R. Wfflstatter and M. Heidelberger, Ber. 46, 517, 1913.
(121) R. Wfflstfttter and H. Veraguth, Ber. 38, 1975, 1905.
(122) R. Willstfttter and E. Waser, Ber. 44, 3423, 1911.
(123) A. Windhaus and J. Brunken, Z. physiol, Chem. 140, 47, 1924.
580
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P. t C.
@ 760mm
tit
*s
Additional Data
Calamenene
136 to 140
0.942
1.5239
@ 12mm
16
@16
Dehydrobetulene
HS
112 to 1 14 67
0.9 186"
1.5052 "
@9mm
@23
@23
C 18 H M
Dinormenthadiene
170 to 172
@ 16mm
Abietine also
"Diterebentyl"
253 to 255 16
0.977 w
@82to
85mm
210 to 211 ss
@ 26.5mm
199 to 200
@ 13mm
581
Hydrocarbons of
Undetermined Structure
B. P., C.
@ 760mm
. Iff
-8
Additional Data
I-Bifenchene
W B 5.13-
321 to 325 6
0.9488 M
1. 50762 M
@ 751mm
@15
7-Camphorene
176tol78 J8
0.8875 28 *
1.5030 28 *
@4.5mm
19
@19
Colophen
318 to 320 18
crCryptomerene
W c - +34.22 M
6160
345 eo
198 60
@ 15mm
0-Cryptomerene
212 W
with
s u b -
lima-
tion
582
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
<& 760mm
#
s
Additional Data
CnHjn-S
Dacrene
951,7
1.5120 7
(' 13
Briggs states that
Dacrene, Sciadopi-
tene, and Phyllocla-
dene are identical
and that the use of
the names Dacrene
and Sciadopitene
should be discon-
tinued in the litera-
ture.
Dicarvenene
170 to 173"
0.928 <
1.5175 4e
@. 10mm
Dicinene
329 to 334 32
328 to 333 23
182 32
@ 13mm
Diisocarvestrine
188to 190 l9
20mrn
583
Hydrocarbons of
Undetermined Structure
M. P. f C.
B. P., C.
@ 760mm
Iff
^
Additional Data
Diisochamene
4-- -0.7-
155 to 156
0.9150
1.5134"
@ 4mm
Dipinene
183 to 184 "
0.9260"
1.5174 u
@ 15mm
Diterpene
[a]j; 61 ~-i.n*
57 to 58 24
55.5 38
320 M
184 to 186 24
@ 10mm
0.963 1 24
@60
0.9686 24
1.5132*
60
1.5150*
140 to 142 24
@ 1mm
1.5208*
@25
1.5244"
Diterpene
H.--
178 52
Diterpene
156 to 160 42
0.8966 42
1.5048 42
@ 13mm
n 20
Z/20
CM HIS
584
Hydrocarbons of
Undetermined Structure
M.PSC.
B. P., C.
760mm
iff
s
Additional Data
Diterpene from 1-
Pinene and Limonene
in the presence of HC1
330 to 332 "
174 to 178 M
@ llmm
0.932 M
@ 17.5
1.51983"
Diterpene
180tol85 20
@ 15mm
0.9309 20
1.5168 20
30
Diterpene
142 to 143 2
@ 4mm
0.8654 2
1.5080'
@23
Diterpenes from
/-a-Phellandrene
W- + 14.96 "
182 to 184 12
@ 16mm
0.9257 M
1.5171"
oil from Eucalyptus
dives
[]- + 13.20"
193 to 195 "
0.9245 "
1.5178"
585
C N H,,
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
@ 760mm
DT
n D
Additional Data
oil from Eucalyptus
phellandra
MS- 4-3.28
194 to 196 12
0.9272
1.5173 l8
@24mm
oil from Melaleuca
[K-f 1.00 w
acuminata
191 to 193 12
0.9303 l2
1.51813 12
Diterpene
173 to 183
0.9361 41
1.5170 4l
@ 13mm
Diterpene with 3
double bonds
170"
0.923 "
1.5143"
@ 12mm
Diterpene-bicyclic with
3 double bonds
M.- + UT.
178 to 180*
0.8892 40
1.4884*
@ 6mm
C je HM
586
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
@ 760mm
tif
*s
Additional Data
Diterpilene
210 to 212 3 <
0.9404 84
Isodacrene
[],,- +48.4'
107 <
107 l
Isophyllocladene
[]-+ 23.4
110.5 to
112 9
108 to
109 10
Methylabietine
135 to 138"
0.9734 45
1.5313 45
@ 0.15mm
24
587
Hydrocarbons of
Undetermined Structure
f. P.C.
J5. P., C.
@ 760mm
pr
s
Additional Data
CnH 2 n-8
Phyllocladene
95
98
<x] D ~+ 16.06
Pinaconane
98 s
a-Podocarprene
L5-11M1-
SO 38
/3-Podocarprene
[^-13.88-
188 to 190 38
0.9688 38
1.5203 38
6-Podocarprene
I Jjj
65 20
^
Sclarene
W.-14-
125 to 128
@ 0.2mm
0.9388 * 8
17
1.5217
588
Hydrocarbons of
Undetermined Structure
M.PSC.
B. P. t *C.
@ 760mm
D?
4
Additional Data
CnH.jn-8
Tetracyclic Diterpene
[]-- 25.1
185 to 186
@ 12mm
0.9648 "
1.5185"
@25
Tricyclic Diterpene
179 to 182 3
@ 12mm
0.9482
C.H.
135 2
@ 0.2mm
0,921 2 2
@16
1.5114 2
16
CTT
23 -Lite
79 63
Dehydrocholane
213 to 218"
@ 12mm
2 10 to 213
@ 12mm
589
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
@ 760mm
or
g
Additional Data
C n H 2 n-8
Amyranene
182 to
183"
Bombicestene
91 to
92 8o
Inagostene
Wg--50.7
89"
Lupene
180 to
181"
Microcionastene
61 to
62
C,,H,
590
Hydrocarbons of
Undetermined Structure
M. P.C.
B. P., C.
@ 760mm
D?
n
Additional Data
Neocholestene
-
71 to
7422
Pseudositostene
69
Soja-7-sitostene
[] fl =-59.3
738
76 to
77"
a-Ergostene
WS-+H
77 to
78 22a
0-Ergostene
[] B =+2t.3 b
87 to
86 to
87 15
78"
591
1/27 XI 41
Hydrocarbons of
Undetermined Structure
M. P.fC.
@ 760mm
Of
*S
Additional Data
A 24 -Pseudoergostene
[!=+ 20.3
103 1 *
Cryptostene
Wg .+M.i. M
74.5 to
76 54
592
(1) P. W. Aitkens, J. Soc. Chem. Ind. 47T, 223, 1928.
(2) B. Arbusov, Her. 67, 563, 1934.
(3) P. R. Balas and Z. Pejsova, Collection Czechoslovak, commun. 2, 424, 1930.
(4) G. B. Beath, J. Soc. Chem. Ind. 52T, 338, 1933.
(5) B. Beckmann, Ann. 292, 1, 1896.
(6) W. Bergmann and T. B. Johnson, Z. physiol. Chem. 222, 220, 1933.
(7) W. J. Blackie, J. Soc. Chem. Ind. 48T, 357, 1929.
(8) K. Bonstedt, Z. physiol. Chem. 176, 269, 1928.
(9) L. H. Briggs, J. Chem. Soc. 1937, 79.
(10) L. H. Briggs, J. Soc. Chem. Ind. 56, 137, 1937.
(11) L. H. Briggs and W. F. Short, J. Chem. Soc. 1928, 3118.
(12) P. G. Carter, H. G. Smith, and J. Read, J. Soc. Chem. Ind. 44T, 543, 1925,
(13) Deville through S. Uchida, J. Am. Chem. Soc. 38, 687, 1916.
(14) H. Dieterle and A. Salomon, Arch. Pharm, 270, 495, 1932.
(15) J. L. Dunn, I. M. Heilbron, R. P. Phipers, K. M. Samant, and F. S. Spring, J. Chem. Soc. 1934,
1576.
(16) T. Easterfield and G. Bagley, J. Chem. Soc. 85, 1238, 1904.
(17) P..Ebel and M. W. Goldberg, Helv. Chim. Acta 10, 677, 1927.
(18) E, Fernholz, Ber. 69, 1792, 1936.
(19) K. Fisher and W. H. Perkin, J. Chem. Soc. 93, 1876, 1908.
(20) C. S. Gibson and J. L. Simonsen, J. Chem. Soc. 1929, 305.
(21) C. Harries, per. 35, 3256, 1902.
(22) K. Hattori and C. Kowasaki, J. Pharm. Soc. Japan 57, 588, 1937.
(22a) I. M. Heilbron, F. S. Spring, and E. T. Webster, J. Chem. Soc. 1932, 1705.
(22b) I. M. Heilbron and D. G. Wilkinson, J. Chem. Soc. 1932, 1708.
(23) C. Hell and H. Sturcke, Ber. 17, 1970, 1884.
(24) J. R. Hosking, Rec, trav. chim. 47, 578, 1928.
(25) J. R. Hosking and C. Brandt, Ber. 68, 237, 1935.
(26) J. R. Hosking and C. Brandt, Ber. 68, 286, 1935.
(27) K. Kafuku and T, Nozoe, Bull. Chem. Soc. Japan 6, 111, 1931; Chem. News 143, No. 3717, 21,
1931.
(28) K. Kafuku, T. Nozoe, and C. Hata, Bull. Chem. Soc. Japan 6, 40, 1931.
(28a) K. Kafuku, Ozamada, and Nishi, J. Chem. Soc. Japan 54, 364, 1933.
(29) J. Kawamura, Bull. Imp. Forestry Exp. Station Japan, No. 31, 93, 1931.
(30) K. Kowasaki, J, Pharm. Soc. Japan 55, 758, 1935.
(31) K. Kowasaki, J. Pharm. Soc. Japan 56, 76, 1936.
(32) E. Knoevenagel, Ann. 402, 111, 1914.
(33) I. L. Kondakow and S. Saprikin, Bull. soc. chim. [4] 37, 1045, 1925.
(34) L. Lafont, Ann. chim. [6] 15, 145, 1888.
(35) P. Levy, Ber. 39, 3043, 1906.
(36) K. Matsubara and W. H. Perkin, J. Chem. Soc. 87, 661, 1905.
(37) F. H. McDowaU and H. J. Finlay, J. Soc. Chem. Ind. 44T, 42, 1925.
(38) K. Nishida and H. Uota, Bull. Agr. Chem. Soc. Japan 7, 1, 1931.
(39) K. Nishida and H. Uota, J. Agr. Chem. Soc. Japan 11, 489, 1935.
(40) G. V. Pigulevski, E. T. Kanetskaya, and M. A. Platonova, J. Gen. Chem. (U.S.S.R) 7, 873, 1937.
(41) K. C. Roberts, J. Chem. Soc. 127, 2451, 1925.
(42) S. Ruheman, Z. angew. Chem. 44, 75, 1931.
(43) L. Ruzicka and M. M. Janot, Helv. Chim. Acta 14, 645, 1931.
(44) L.,Ruzicka, J. Meyer, and M. Mingazzini, Helv. Chim. Acta 5, 345, 1922.
(45) L. Ruzicka, H. Waldman, P. Meier, and H. H6sli, Helv. Chim. Acta 16, 169, 1933.
(46) F. W. Semmler, Ber. 42, 522, 1909. *
(47) F. W. Semmler, K. G. Jonas, and F. Richter, Ber. 51, 417, 1918.
593
(48) H. Smith, J. Soc. Chcm. Inch 30, 1353, 1911.
(49) H. Staudinger and H. A. Bruson, Ann. 447, 97, 1926.
(50) S. Uchida, J. Am. Chem. Soc. 38, 687, 1916.
(51) H. Uota, J. Dept. Agr. Kyushu Imp. Univ. 5, 118, 1937.
(52) H. Weinhaus, Nordiska Kemistmotet, 1926, 211.
(53) H. Wieland, Z. physiol. Chem. 142, 191, 1925.
(54) H. Wieland, H. Pasedach, and A. Ballauf , Ann. 529, 68, 1937.
(55) A. Windaus and J. Brunken, Z. physiol. Chem. 140, 52, 1924.
(56) O. Zeitschel, Ber. Schimmel and Co. Akt. Ges. 1929, 319.
594
Hydrocarbons of
Undetermined Structure
M. P.,*C.
B. P., C.
760mm
/?r
s
Additional Dula
C w H,2/-10
crCholesterylene
W^-- 116.20 1J>
79 to
257 to 267 20
0.9572 20
1. 52027 20
[a]^-- 109.30 22
80
@ 12mm
o
79 20.21
laj^^-107 023
78,2 l2
78 3 - 10
[ak-- 102.1 10
77 22,23
[a] i) --6I.S5
75.5 2
00
74 to
W /) =-47.7 20
76"
[] -1 7.53 > 2
/3-Cholesterylene
593
a-Ergostadiene
[aB 10-
124 to
/3-Ergostadiene
Wg 33-
66 to
67 9
Dehydroergostene
fcfl-13-
71 to
72"
595
Hydrocarbons of
Undetermined Structure
M. JVC.
(f(} 7 60 mm
of
"3
/I dflifioiHil Data
Amyrene
Wg- 4-44.9 *
(> 15mm
cr Amyrene I
WJJ-+72.2-
96 to
97,5 2 <
/3-Amyrene
98 '
252 '
^ 1 2mm
$-Amyrene Ib
[ a ] as ^.98.9 24
104"
^-Amyrene I
[^=4-77.6^
89 to
91. 5 24
jff-Amyrene la
[]w4-115
209 to
210 2 <
a-Amyrene II
120 to
122"
0-Amyrene II
[<-+M.6^
162 24 *
-Amyrene III
W--22 P
187 to
189.5 2<
596
Hydrocarbons of
Undetermined Structure
M. JVC,
B. P., C.
(5>/ 760mm
tif
s
Additional Data
On-H.2M-.lo
Amyrene (Continued)
/3-Amyrene IV
Mj;=+57.3 24
159 to
161 24
Dihydro-o-amyrilene
[<*]**+ 120.2 >
84 to
0.841 16
85 >
(solid)
Dihydro-0-amyrilene
I
83 to
0.846 16
|aj y> =-fl3t.5 0j
85 "
(solid)
II
92 to
0.941 17
[<*]= +7 7'^
93"
@102
Friedelene
257 to
258*
Isolanostene
80 to
81
597
CsoHso
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
@ 760mm
cff
*S
Additional Data
CttH.2n-.10
Lanostene
76 to
776
Oleanene
[j^+56.5"
193 25
Oleanene I
113 to
116 24
Oleanene II
193 24
Oleanene III
Wg=+30.1 2 *
225 to
226 2 <
598
Hydrocarbons of
Undetermined Structure
M. P. t C.
B. P., C.
@ 760mm
i>5
-8
Additional Data
CJHan-10
Iso-tetracyclosqualene
228 to 230 8
0.9237 8
1.5098 s
< 3mm
D 20
a-Viscane
98
-Viscane
136 1
Methyl friedelene
272 to
274 6
C H
Thevetene
79 to
80 '
599
(1) K. H. Bauer and V. Girloff, Arch. Pharm. 274, 473, 1936.
(2) A. Bloch, Bull. soc. chim. [3] 31, 71, 1904.
(3) A. T. Bose and W. Doran, J. Chem. Soc. 1929, 2244.
(4) H. Dieterle, A. Salomon, and E. Herzberg, Arch. Pharm. 269, 78, 1931.
(5) N. Drake and W. Campbell, J. Am. Chem. Soc. 58, 1681, 1936.
(6) C. Doree* and V. A. Petrov, J. Chem. Soc. 1936, 1562.
(7) N. Ghatak and G. P. Pendse, Bull. Acad. Sci. United Provinces Agra Oudh, India, 2, 259, 1933.
(8) J. Harvey, I. M. Heilbron, and E. D. Kamm, J. Chem. Soc. 1926, 3136.
(9) I. M. Heilbron, P. S. Spring, and E. T. Webster, J. Chem. Soc. 1932, 1705.
(10) I. M. Heilbron, R. A. Morton, and W. A. Sexton, J. Chem. Soc. 1928, 47.
(11) R. E. Marker, O. Kamm, T. S. Oakwood,and J. Laucius, J. Am. Chem. Soc. 58, 1948, 1936.
(12) E. Miller and I. H. Page, J. biol. Chem. 101, 127, 1933.
(13) E. Montigne, Bull. soc. chim. [5] 2, 1367, 1935.
(14) A. Morrison and J. Simpson, J. Chem. Soc. 1932, 1710.
(15) F. Nord, Biochem. Z. 99, 261, 1919.
(16) L. Ruzicka, H. Silbermann, and M. Furter, Helv. Chim. Acta 15, 482, 1932.
(17) L. Ruzicka, H. Silbermann, and P. Pieth, Helv. Chim. Acta 15, 1285, 1932.
(18) F. S. Spring, J. Chem. Soc. 1933, 1345.
(19) W. Steinkopf and E. Blummer, J. prakt. Chem. [2] 84, 460, 1911.
(20) W. Steinkopf, H. Winternitz, W. Roederer and A. Wolynski, J. prakt. Chem. [2] 100, 65, 1920.
(21) A. Windaus, Z. physiol. Chem. 117, 146, 1921.
(22) L. Tschugaeff and W. Fomin, Ann. 375, 288, 1910.
(23) L. Tschugaeff and Gasteff, Ber. 42, 4631, 1909.
(24) A. Winterstein and G. Stein, Ann. 502, 223, 1933.
(25) A. Winterstein and G. Stein, Z. physiol. Chem. 202, 217, 1931.
600
Hydrocarbons of
Undetermined Structure
M. P. t *C,
B. P,, C.
@ 760mm
Iff
s
Additional Data
CnH.2n-.12
Chamazulene
159"
0.9881 l7
@ 1 1 mm
@18
Elemazulene
0.9355 14
0.9735 14
S-guaiazulene
167 to 168 u
0.9333 "
@ 12mm
@80
164"
0.9712 I4
@ llmm
<>23
0.9728 "
0.9759 17
Diterpene
194 to 199 10
0.9494 >
1.5303 I0
% 17mm
0.9244 I0
1.S280 10
190 to 194 l
<$ 14mm
601
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P, t C.
@ 760mm
m
'
Additional Data
CnHjn-12
Dihydroergotetraene-A
Mg-+121"
98i8
Ergostatriene-D
[! 4-42.7
134 to
135
Oleanylene
Wg- 496,4 2 <
185 to
186 2 <
Oleanylene
182"
Oleanylene I
[]+ 78.9
145 to
14923
Oleanylene II
186 23
Oleanylene III
178 to
182 23
602
Hydrocarbons of
Undetermined Structure
M. P.,C.
B. P., C.
@ 760mm
DT
fig
Additional Data
CfJH.2n-.lS
a-Amyrilene
Ma- +109.48"
ef-form
135 2l
450 M
0.9532 '
1.5107"
M0- + 109.5"
134 ""
285"
137.0
137.0
134 to
15mm
135
133 to
134"
/-form
[a]^ -- 104.9 l2
193 to
194 20
a-Amyrilene I
133 to
235 "
0.9857 16
1.5420"
135 2S
O.lmm
38
38
a-Amyrilene II
[]-+ 136.6 *
119 to
120 23
/3-Amyrilene
[a],,- +112.19"
175 to
235 18
0.9268 l6
1.4973 lft
[1 1 1 1 1 7 SI
Qfl = -J 111.^ **
! 78 i9,2i
O.lmm
173.2
173.2
173 to
0.9807 15
1.5409 M
175"
38
603
Hydrocarbons of
Undetermined Structure
M. P.,c
S. P., C.
@ 760mm
Iff
s
Additional Data
CnH.2n-.l2
0-Amyrilene I
170 to
175 23
#-Amyrilene II
[]g- + 139.3
147 to
148 6
148 to
ISO 23
0-Amyrilene III
[!- + 155
103 6
7-Amyrilene
W35-+S4.1 *
175 8
a-Latucene
207
a-Viscene
[15--fl20.2
169 2
C 301:148
604
Hydrocarbons of
Undetermined Structure
M. P.,C
B. P., C.
@ 760mm
*
H D
Additional Data
#-Viscene
161 2
[)JJ-f32.2 *
5-Euphorbodiene
232 to 235 3
@ 5mm
Ergotetraene A
9718
r^U' ss -|- 1 76 ^
Ergotetraene B
105 "
lyyl JO^ 1U
Ergotetraene C
98
-+-
605
Hydro ra rbo ns of
Undetermined Structure
Lumistatetraene
AI.
. p., r.
76()tmu
7/f
88 to
90 8
Additional Data
ia|2J--f 298.9
(1) H. B6ckstrom through A. Vesterberg, Ber. 20, 1245, 1887.
(2) K. H. Bauer and U. Gerloff, Arch. Pharm. 274, 473, 1936.
(3) K. H. Bauer and G. SchrSder, Arch. Pharm. 269, 209, 1931.
(4) K. H. Bauer and E. Schub, Arch. Pharm. 267, 413, 1929.
(5) H. Dieterle, H. Brass, and P. Schoal, Arch. Pharm. 275, 557, 1937.
(6) H. Dieterle, A. Salomon, and E. Herzberg, Arch. Pharm. 269, 78, 1931.
(7) A. Guiteras, Z. physiol. Chem. 215, 196, 1933.
(8) I. M. Heilbron, F. S. Spring, and P. A. Stewart, J. Chem. Soc. 1935, 1221.
(9) I. M. Heilbron, F. S. Spring, and E. T. Webster, J. Chem. Soc. 1932, 1705.
(10) Riki Horiuchi, Mem. Coll. Sci. Kyoto Imp. Univ. Ser. A. 11, No. 3, 171, 1928.
(11) Kenjiro Kitasato, Acta Phytochem., Japan 8, 207, 1935.
(12) v. Koch through A. Vesterberg, Ber. 24, 3835, 1891.
(13) H. Matthes and O. Rohdich, Ber. 41, 19, 1908.
(14) L. Ruzicka and A. J. Haagen-Smit, Helv. Chim. Acta 14, 1104, 1931.
(15) L. Ruzicka, H. W. Huyser, M. Pfeiffer, and C. F. Seidel, Ann. 471, 21, 1929.
(16) L. Ruzicka and E. Rudolph, Helv. Chim. Acta 9, 118, 1926.
(17) L. Ruzicka, H. Silbermann, and M. Furter, Helv. Chim. Acta 15, 482, 1932.
(18) O. Rygh, Z. physiol. Chem. 185, 99, 1929.
(19) A. Vesterberg, Ber. 20, 1242, 1887.
(20) A. Vesterberg, Ber. 24, 3834, 1891.
(21) A. Vesterberg, Ber. 24, 3836, 1891.
(22) K. A. Vesterberg and S. Westerlind, Ann. 428, 247, 1922.
(23) A. Winterstein and G. Stein, Ann, 502, 223, 1933.
(24) A. Winterstein and G. Stein, Z. physiol. Chem. 202, 222, 1931.
American Chemical Society
MONOGRAPH SERIES
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1. The Chemistry of Enzyme Action (Revised Edition). By K. George Falk.
2. The Chemical Effects of Alpha Particles and Electrons (Revised Edition).
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3. Organic Compounds of Mercury. By Frank C. Whitmore. (Out of Print)
4. Industrial Hydrogen. By Hugh S. Taylor.
5. Zirconium and Its Compounds. By Francis P. Venable.
6. The Vitamins (Revised Edition). By H. C. Sherman and S. L. Smith.
7. The Properties of Electrically Conducting Systems. By Charles A. Kraus.
8. The Origin of Spectra. By Paul D. Foote and F. L, Mohler. (Out of Print)
9. Carotinoids and Related Pigments. By Leroy S. Palmer.
10. * The Analysis of Rubber. By John B. Tuttle.
11. Glue and Gelatin. By Jerome Alexander. (Out of Pritrt)
12. The Chemistry of Leather Manufacture (Revised Edition). By John A. Wilson.
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13. Wood Distillation. By L. F. Hawley. (Out of Print)
14. Valence and the Structure oi Atoms and Molecules. By Gilbert N. Lewis,
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15. Organic Arsenical Compounds. By George W. Raiziss and Jos. L. Gavron.
16. Colloid Chemistry (Revised Edition). By The Svedberg.
17. Solubility (Revised Edition). By Joel H. Hildebrand.
18. Coal Carbonization. By Horace C. Porter. (Revision in preparation)
19. The Structure of Crystals (Second Edition) and Supplement to Second Edi-
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20. The Recovery of Gasoline from Natural Gas. By George A. Burrell.
21. The Chemical Aspects of Immunity (Revised Edition). By H. Gideon Wells.
22. Molybdenum, Cerium and Related Alloy Steels. By H. W. Gillett and E. L.
Mack.
23. The Animal as a Converter of Matter and Energy. By H. P. Armsby and
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24. Organic Derivatives of Antimony. By Walter G. Christiansen.
25. Shale Oil. By Ralph H. McKee.
26. The Chemistry of Wheat Flour. By C. H. Bailey.
27. Surface Equilibria of Biological and Organic Colloids. .By P. Lecomte du
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28. The Chemistry of Wood. By L. F. Hawley and Louis E. Wise.
29. Photosynthesis. By H. A. Spoehr. (Out of Print)
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31* Equilibria in Saturated Salt Solutions. By Walter C. Blasdale.
32. Statistical Mechanics as Applied to Physics and Chemistry. By Richard C.
Tolman. (Out of Print)
33. Titanium. By William M. Thornton, Jr.
34. Phosphoric Acid, Phosphates and Phosphatic Fertilizers. By W. H. Waggaman.
35. Noxious Gases. By Yandell Henderson and H. W. Haggard. (Revision in
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36. Hydrochloric Acid and Sodium Sulfate. By N. A. Laury.
37. The Properties of Silica. By Robert B. Sosman.
38. The Chemistry of Water and Sewage Treatment. By Arthur M. Bnswell.
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39. The Mechanism of Homogeneous Organic Reactions. By Francis O. Rice.
40. Protective Metallic Coatings. By Henry S. Rawdon. Replaced by Protective
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41. Fundamentals of Dairy Science (Revised Edition). By Associates of Rogers.
42. The Modern Calorimeter. By Walter P. White.
43. Photochemical Processes. By George Kistiakowsky.
44. Glycerol and the Glycols. By James W. Lawrie.
45. Molecular Rearrangements. By C. W. Porter.
46. Soluble Silicates in Industry. By James G. Vail.
47. Thyroxine. By E. C. Kendall.
48. The Biochemistry of the Amino Acids. By H. H. Mitchell and T. S. Hamilton.
(Revision in preparation)
49. The Industrial Development of Searles Lake Brines. By John E. Teeple.
50. The Pyrolysis of Carbon Compounds. By Charles D. Hurd.
51. Tin. By Charles L. Mantell.
52. Diatomaceous Earth. By Robert Calvert.
53. Bearing Metals and Bearings. By William M. Corse.
54. Development of Physiological Chemistry in the United States. By Russell H.
Chittenden.
55. Dielectric Constants and Molecular Structure. By Charles P. Smyth. (Out of
Print)
56. Nucleic Acids. By P. A. Levene and L. W. Bass.
57. The Kinetics of Homogeneous Gas Reactions. By Louis S. Kassel.
58. Vegetable Fats and Oils. By George S. Jamieson.
59. Fixed Nitrogen. By Harry A. Curtis.
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Huffman.
61. The Catalytic Oxidation of Organic Compounds in the Vapor Phase. By L. F.
Marek and Dorothy A. Halm
62. Physiological Effects of Radiant Energy. By H. Laurens.
63. Chemical Refining of Petroleum. By Kalichevsky and B. A. Stagner. (Out of
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64. Therapeutic Agents of the Quinoline Group. By W. F. Von Oettmgen.
65. Manufacture of Soda. By T. P. Hou. (Revision in Preparation)
66. Electrokinetic Phenomena and Their Application to Biology and Medicine.
By H. A. Abramson.
67. Arsenical and Argentiferous Copper. By J. L*. Gregg.
68. Nitrogen System of Compounds. By E. C. Franklin.
69. Sulfuric Acid Manufacture. By Andrew M. Fairlie.
70: The Chemistry of Natural Products Related to Phenanthrene (Second Edition
with Appendix). By L. F. Fieser.
71. The Corrosion Resistance of Metals and Alloys. By Robert J. McKay and
Robert Worthington.
72. Carbon Dioxide. By Elton L. Quinn and Charles L. Jones.
73. The Reactions of Pure Hydrocarbons. By Gustav Egloff.
74. Chemistry and Technology of Rubber. By C. C. Davis and J. T. Blake.
75. Polymerization. By R. E. Burk, A. J. Weith, H. E/Thompson and I. Williams.
76. Modern Methods of Refining Lubricating Oils. By V. A. Kalichevsky.
77. Properties of Glass. By George W. Morey.
78. Physical Constants of Hydrocarbons. By Gustav Egloff. Vol. I.
79. Protective Coatings for Metals. By R. M. Burns and A. E. Schuh.
80. Raman Effect and its Chemical Applications. By James H. Hibben.
81. Properties of Water. By Dr. N. E. Dorsey.
82. Mineral Metabolism. By A. T. Shohl.
