Frances S.
Sterren I The Nature of Essential Oils
Hofstra College
Hernpsteod, New York I Chemical constituents, analysis
Essential oils are composed of many
classes of chemical substances. One oil may consist of
as many as 75 individual constituents (as in the case of
oil of camphor wood), or may contain largely one chem-
ical compound (for example oil of sweet birch contains
98% methylsalicylate, oil of anise 90% anethole).
Even though essential oils usually consist of complex
mixtures of acyclic, cyclic, aromatic, and heterocyclic
compounds and their oxygenated derivatives, most of
the constituentsfall into four main groups: (1) aliphatic,
non-terpenic compounds, (2) aromatic compounds, (3)
terpenes and terpenoids, and (4) miscellaneous.
Aliphatic Compounds Excluding Terpenes
A few aliphatic hydrocarbons have been found and
isolated in essential oils, e.g. heptane from pine needle
oil. "Stearoptenes, "whichconsist of amixtnreof waxes,
contain higher members of the paraffin series. This
wax-like material, probably originating from the pro-
tective coatings of leaves, flowers, fruits, and seeds, is
found in oils of rose and camomille in such large amounts
that these oils readily congeal below room temperature.
Waxes are also found in rather large percentage in cold-
pressed citrus oils. Essential oils contain only a few
aliphatic alcohols and acids in free form; most of them
are esterfied. The lower, water-soluble members of the
saturated aliphatic alcohols, such as methyl and ethyl
alcohol, and acids such as formic, acetic, propionic,
butyric, and valeric acid occur in oils of "cohobation"
obtained by redistillation of the distillation water.
These alcohols and acids are probably degradation
products formed by such processes as hydrolysis dur-
ing steam distillation or fermentation prior to distilla-
tion. Saturated aliphatic alcohols such as butyl, amyl,
hexyl, octyl, nonyl, decyl, undecyl in the form of normal
or branched isomers have been isolated by fractional
distillation from a variety of essential oils. The un-
saturated aliphatic alcohol 3-hexen-1-01, the so-called
"leaf alcohol," occurs in many green leaves, herbs, and
grasses; it has a characteristic grasslike odor and is the
main constituent of tea leaf oil. Methyl heptenol
isomers are formed in lemon-grass oil. 2,6-Nonadien-
1-01, called "violet leaf alcohol," has been observed in
violet leaf and flower oils (1) and androl (1-nonen-3-01)
in the distillation water of fennel oil.
The lowest members of aliphatic aldehydes (non-
terpenic) do not play an important role in essential oils.
For instance formaldehyde and acetaldehyde occur in
distillation waters and are probably decomposition or
degradation products formed in the course of steam
The first pert of this two-part paper dwcrihed the production of
essential oils. See J. CHEM.E ~ u c .39,
, 203 (1962).
distillation. Propyl, butyl, valeral, and caproaldehyde
occur, for example, in the lower fractions of eucalyptus
and peppermint oils. The higher aliphatic aldehydes,
such as octyl and nonyl, even though contained only in
minute quantities, play a more prominent role, due to
their characteristic powerful odor and flavor. They
are contained in such oils as orris root, coriander seed,
rose, lemon, and sweet orange. An unsaturated ali-
phatic aldehyde, beta hexanal ("leaf aldehyde") con-
tributes to the green leaf odor. 2,6-Nonadien-1-a1
called "violet leaf aldehyde" occurs in violet leaf oil (I).
Not many aliphatic ketones occur in essential oils.
Again, the lowest members, such as acetone and di-
acetyl, are formed mainly in distillation waters and are
probably decomposition products. Amy1 methyl ke-
tone has been found in the lower boiling fractions of
clove oil, and methyl hept,enone in many essential oils.
The following fatty acids have been found mostly in
essential oils from seeds and roots: alpha and beta-
methyl butanoic, caproic, enanthic, caprylic, pelargonic,
capric, nndecylic, lauric, myristic, hydroxy myristic,
palmitic, stearic, methacrylic, isopropylidenacetic,
angelic, tiglic, beta-propylacrylic, oleic, and succinic.
Some essential oils contain large quantities of fatty
acids; thus orris root oil contains up to 85% myristic
acid.
Esters are among the most important constituents
and contribute greatly to the odor and flavor character
of the essential oils. Some oils consist almost entirely
of esters (oil of wintergreen and oil of sweet birch con-
tain up to 99% methyl salicylate). Many alcohols
and acids occur as esters in essential oils. Obviously a
great variety of combinations are possible.
Aromatic Compounds
This group of compounds comprises a number of im-
portant essential oil constituents. The aromatic ring
may have substituted one or more functional groups or
side chains
For example safrole occurs in sassafras oil, myristicin
in nutmeg oil.
Some of the aromatic alcohols found in essential oils
are benzyl, phenylethyl, phenylpropyl, cinnamyl, and
cuminyl.
A number of the aromatic aldehydes play an impor-
tant role in essential oils; for example, cinnamic aldehyde
 is the main constituent of cassia oil and cinnamon oil.
Some of the more important aromatic aldehydes occur-
ring in essential oils are benzaldehyde, cumaldehyde,
phenylacetaldehyde, cinnamaldehyde, dihydrocinna-
maldehyde, vanillin, vanillin methyl ether ("methyl
vanillin,") piperonal (or heliotropin; 3,4-methylene di-
oxybenzaldehyde). Aromatic ketonesoccur very rarely
in natural essential oils, but some synthetic compounds
such as acetophenone and substituted derivatives are
widely used in floral-type synthetic perfumes.
Phenols and phenol ethers contribute to the flavoring
ingredients of many essential oils, for example eugenol in
oil of clove, methyl chavicol in oil of estragon, and
safrole in oil of sassafras. In other oils the phenols are
responsible for the antiseptic and germicidal properties
of the oils; for example thymol in oil of thyme and car-
vacrol in oil of origanum. Thus, the phenols and phenol
ethers belong among the most important constituents
of essential oils. Some of them are isopropylphenol,
thymol, carvacrol, chavicol, methylchavicol, anethol,
fenicnlin, p-an01 eugenol (main constituent of oil of
clove, cinnamon leaf, and pimenta), eugenol acetate,
methyl eugenol, isoeugenol, methylisoeugenol, safrole,
isosafrole, myristin, isomyristin, elemicin, and eugenone.
Some quinones and hydroqninones have been found to
occur in some essential oils, probably as glncosides.
Aromatic acids are present in essential oils free and/
or as esters; for example benzoic, phenyl acetic, cin-
narnic, salicylic, anisic, piperonylic, veratric, and meth-
oxy cinnamic acid. Some of the aromatic esters found
are benzylhenzoate, methyl salicylate (main constituent
of oils of wintergreen and sweet birch). Methylethyl-,
benzyl and cinnamyl-cinnamate, and isoamyl salicylate
are important synthetic aromatic chemicals.
Many members of the essential oil constituents are
related through simple chemical reactions. For ex-
ample isomerization followed by oxidation may convert
eugenol through isoeugenol to vanillin, a constituent of
vanilla oil (3, 3).
OCH. OCH~
Eugenol Isoeugenol
OCHa
Vmillin Acetaldehyde
The tendency of some essential oil derivatives to
resinify is probably due to the number of conjugated
double bonds in the structure, which readily form con-
densation products.
Lactones are quite widely distributed in nature; the
most important which occur in essential oils are the
coumarins, coumarone derivatives, and some furano
coumarins. Conmarin (4) can be considered derived
from o-hydroxy cinnamic acid:
Coumarins occur in many plants as glucosides and thus
often the plant itself is odorless, but coumarin may be
liberated due to enzyme action. Coumarins as such
probably contribute to the odor of hay, which develops
upon drying of the foliage in the sun. Most coumarins,
coumarone, and furano conmarine derivatives have high
boiling points; since they are only sparingly volatile
with steam, they are found mainly in extracted and ex-
pressed oils. For example 5-methoxy-furo(3',Zf,6,7)
coumarin in oil of bergamot, angelicin [furo (5',4',7,8)
coumarin] in oil of angelica root, limettin (5,7-dimeth-
oxycoumarin) in oils of lemon and lime, umbelliferone
(7-hydroxycoumarin) in grapefruit oil, and umbelli-
ferone methyl ether in oils of chamomile and lavender.
Different isomers of the same chemical substance
often vary greatly in odor and flavor. Six of the mono-
substituted methyl coumarins were prepared as pure as
possible in order to determine their odor character and
their utility in flavor compounds (5); all six are white
crystalline solids.
Comoorison of Methyl Coumorinr
Position of
methvl srour, Odor
3- Coumarin-like
4- Walnut-like
5- Between 3 and 4
6- Pleasant coconut odor
7- Very faint coconut-like
8- Almost odorless
Terpenes and Terpenoids
The most widely distributed compoimds present in
essential oils are the terpenes and sesquiterpenes, and
their oxygenated compounds. I n fact, the scient,ific
literature on the subject of terpenes and terpenoids has
grown very large (6-11).
-
The English word "ter~ene"is derived from the Ger-
man word "Terpentin" (turpentine, or oil of turpentine,
a product subject to much research and known to the
ancient Greeks). The term "terpene" refers to hydro-
carbons which have a chemical relationship to the
simple isoprene (C6Hs) molecule. "Terpenoids" (in
analogy with the term steroids) are compounds having
features relating them to the terpene structure. The
terms terpene and terpenoids usually refer not only to
the hydrocarhons but also to their oxygenated com-
pounds.
The members of the terpene group can conveniently
be classified into compounds containing branched
five-carbon chains: hemiterpenes (1 isoprene unit),
monoterpenes (2 isoprene units), sesquiterpenes (3 iso-
prene units), diterpenes (4 isoprene units), and poly-
terpenes.
The most characteristic group present in essential oils
are the monoterpenes and their oxygenated compounds
with the empirical formulas CloHlr; CIOHEO;CioHi~0.
It is purely hypothetical to assume that a Cb chain
actually represents the basic unit in the formation of the
terpenes in the plants. Many terpene investigators
have risked guesses as to the nature of the basic unit.
Isoprene is often mentioned as a precursor in biogenesis
of terpenic compounds. The mechanism of the biologi-
cal chemical reaction should be considered with critical
reserve. I n vilro it has been possible to synthesize a
number of terpenes in accordance with the isoprene rule
(13-16). The formulas written here show the principal
Volume 39, Number 5, Moy 1962 / 247
structural details by omitting as many carbon and
hydrogen symbols as feasible, showing double bonds,
functional groups, and in some cases (where indicated)
methyl and methylene groups.
ture, but forms readily by rearrangement from myrcene,
for example by application of heat.
The same terpenic substance may be reported in
various literature references under different names;
therefore uniformity of nomenclature could quite often
solve rather involved problems (%).
Several stages of oxidation and reduction of acyclic
terpene hydrocarbons are shown below:

-reduction

oridation

Dipentene (Limanene) Isomers Citml

(ClaHx,O)

3 Isoprenes
A

The biogenetic isoprene rule can be considered as a

useful working hypothesis, helpful for the elucidation of
the structure of the terpene compounds. However,
bH0-
- reduction

oxldatlon

there are also many compounds which do not comply

with the isoprene rule. Several other hypotheses were
postulated, e.g., condensation of 3-methyl butenal (16) ;
formation of terpenes and benzene derivatives from con-
densations and degradation of sugar derivatives; and
synthesis from acetone, acetaldehyde, and acetoacetic QOOH
acid (17-20). In recent work on the biosynthesis of
terpenes (Sf), isopentenyl was found to be the basic
unit. 14Glabeled isopentenyl-pyrophosphate, after Citronellic acid
isomerization and stepwise reaction, yields terpene hy- Many terpenes are named commonly after the plant
drocarbons of the general formula
from which they have been isolated, e.g. geraniol from
CHJ 0 0 oil of geranium, linalool from oil of linaloe, citronellol

I. , I
--O--P-O-P--OH
OH
I/
AH
and citronella1 from oil of citronella, etc.
Terpenes are very unstable and readily undergo
molecular rearrangement; structural variations of the
same empirical formula are found frequently:
where n = 1, 2, or 3 depending on the terpene synthe-
sized. Among other terpenes, geranyl pyrophosphate
and farnesyl pyrophosphate were prepared.
Terpenes occurring in essential oils may be acyclic,
monocyclic, bicyclic, and tricyclic. A saturated acyclic
hydrocarbon with 10 carbon atoms has the formula
C l a n ; a compound CloHlamay be acyclic with three
double bonds, or monocyclic with two double bonds, or
bicyclic with one double bond, or tricyclic with no
double bonds. However, terpenes occur in many stages
of oxidation or reduction; therefore, compounds with
more or fewer hydrogens are also found. The oxygenated
derivatives may contain all kinds of functional groups
such as hydroxyl, methoxyl, carbonyl, carhoxyl, etc.
Examples of acyclic terpenes CloHlswith three double
bonds (formulas are written to indicate possible ring
closures) follow: Geraniol also exists as cis- and trans-isomer. The
cis-isomer is called nerol'after oil neroli bigarade from
which it was isolated.

Myrcene Oeimene
(7-methyl-3-methylene (3,Fdimethyl
1,6-octadiene) 1,3,7-oetatriene)
Nerol Germiol
Ocimene is not considered a product occurring in:na- (cis-isomer) (tms-isomer)

248 / Journal of Chemical Education

 Similar isomerism exists between citronellol and rho-
dinol, and citronella1and rhodinal. The same substance
isolated from various natural sources exhibits difierent
odor values, e.g. geraniol derived from oil of geranium Teresantalie acid (CLOHXO~)
smells somewhat different from that derived from oil of The sesquiterpenes (CI6HZn)can again be acyclic,
rose, palmarosa, or citronella; this is attributed to iso- monocyclic, bi- or tricyclic. Some of the sesquiter-
meric mixtures present. penes occurring in essential oils are:
Most acyclic terpenes form cyclic derivatives under
the influence of acid; for example:

Citral Beta cyclocitral

The morioterpene menthadiene, CloHa, has theoreti-
cally a total of 32 isomers consideringthe position of the
two double bonds, cis- and trans-forms, racernic mix-
tures, and the possible optical antipodes. I n essential
oils, the most frequently encountered cyclic monoter- Alpha- Beta- Gamma-
penes, CIOH16, (menthadienes) are the terpinenes, phel- Bisabolene (Ct.Hu) (83, 24)
landrenes, terpinolenes, and limonenes.

Cedinene (C.H.) (26) Cadinol (CaHzsO)

Alpha- Bets, Gamma-
Tewinenes The most important azulenes (mostly blue-colored
compounds) are usually classified as sesquiterpenes and
are based upon the general formula ($6):

Alphs, Bet*
Phellandrenes

Vetivaeulene Guaiasulene Vetivone Guaiol

(CtbHd C H (CdLzO) (CISHXO)
Terpinolene Lirnonene

Many of these structures can be converted ir to each

other by relatively simple chemical reactions.
Some of the bicyclic monoterpenes are:
To the terpenoid group belong the ionones and irones
(violet odor) :

Alphs, Beta- Alphs, Bets, Gamma

Pinene (CmHu) Fenehene (CjoHx8)
Alpha- Beta-
Ionones (CMHNO)

h A A A
Alphs, Beta- Thujyaloohol Thujone
Thujene (ClaHls) (C,oHuO) (C,oH,,O)
Alpha- Bets, Gamma-
Irones (Cz4H7,0)

By far the largest groups of essential oil constituents

Tricyclic terpenic compounds occur less frequently as
essential oil constituents; an example of tricyclic ter-
pene is:
are terpenes and terpenoids and their oxygenated deriv-
atives. Reactions of terpenes, such as isomerization
(shifting of double bonds as well as cyclization or open-
ing of ring structure), polymerization, hydrogenation,
dehydrogenation, esterification, oxidation, etc., occur
Volume 39, Number 5, May 1962 / 249
rather readily, and many variations of terpenes are
found in essential oils. This article can merely give an
idea of the variety of compounds found as essential oil
constituents.
Miscdlaneous. A few compounds do not belong to
the three groups discussed heretofore. They are nitro-
gen- or sulfur-containing compounds, such as organic
cyanides, indole, skatole, allyl, benzyl, phenylethyl
cyanide, methyl authranilate, and methyl-N-methyl-
anthranilate, which are present in certain peel, flower,
and leaf oils from citrus fruit; organic disnlfides and
sulfides, e.g., allyl sulfides in oil of garlic; organic iso-
thiocyanates, e.g. allyl, butenyl, benzyl, phenylethyl
thiocyanate, as constituents of mustard oil. However,
there are surprisingly few of these compounds present
as essential oil constituents.
Analysis
An analysis for the purpose of identifying an essential
oil is usually not necessary, since the identity is estah-
lished by experts from odor alone. Essential oils are
analyzed chemically for three main purposes: identifi-
cation of essential oil constituents; detection of adulter-
ation; or evaluation of the quality of a commercial oil.
Identification of the individual constituents is done
for research purposes only. For many years the study
of these compounds, which are mostly liquids a t room
temperature, was based on first separating the individ-
ual isomers in as pure a form as possible by fractiona-
tion, then preparing crystalline derivatives and identify-
ing them by means of mixed-melting point determina-
tion with an authentic sample. This method is based
on the general standard qualitative analysis of organic
compounds by their functional groups. However,
attempts to prepare these derivatives often are compli-
cated by the instability of the essential oil constituent
and the fact that even small amounts of isomers, which
are usually present, act as impurities and may interfere
greatly with the preparation of the solid derivative. A
chapter written by the author on "The Preparation of
Derivatives of Essential Oil Constituents" gives more
detailed information (28).
The development of modern instrumentation, such as
vapor-phase chromatography, infrared, near infrared,
visible, ultraviolet spectrophotometry, mass spectrome-
try, and even nuclear magnetic resonance have made it
possible to separate isomers of high-grade purity seldom
achieved before, and have helped to elucidate the struc-
ture of terpene isomers (29, SO).
The analysis for the detection of adulteration of essen-
tial oils is basically the same as the analysis for the
evaluation of the quality of an oil. Adulteration fre-
quently occurs in view of the high cost of many of these
products.
The general procedure of analysis is to give the essen-
tial oil first a preliminary and organoleptic examination.
Color, clarity, viscosity, presence or absence of sedi-
ment, waxes, and water are noted. The study of odor
and in some cases flavor can suggest the presence of
adulterants, which may then be confirmed by special
tests. The trained human nose and taste buds have
often a greater minimal sensitivity than the analytical
instruments used for identification. Standard pro-
cedures for organoleptic tests are carried out (31).
Then physical and chemical properties are analyzed,
250 / Journal of Chemical Education
which include determination of solubility in different
fixed strengths of dilute ethyl alcohol (go%, 80% 70%
60%, 50%), specific gravity, optical rotation, refractive
index. Depending on the oil under consideration,
special tests are carried out, such as acid number, total
ester content, total alcohol content, aldehyde content,
phenol content, congealing point, evaporation residue,
etc. (S2).
The analytical figures obtained in as complex a mix-
ture as an essential oil may contain many or only a few
diierent individual components and do not always rep-
resent the actnal percentage of a single constituent;
e.g., in the case of an ester determination all saponifiable
material is calculated as a certain individual ester (for
example, as linalyl acetate). The analytical figures
obtained are then compared with previous analyses and
published standard data. These figures are valuable
and have great practical signilicance. The relationship
between individual chemical and physical properties is
very revealing and important. However, the inter-
pretation of all data obtained requires ingenuity and
much experience.
The use of modern instrumentation such as gas-phase
chromatography and spectrophotometry is still mostly
restricted to special cases, hut rapid progress is being
made along these lines. Much hope lies in the future
of these instruments. Vapor-phase chromatography
has the unique ability to separate organic compounds,
even very similar isomers and homologues, in a purity
seldom achieved before. The sensitivity of spectro-
photometric determination matches the fine organolep-
tic concentration requirements. However evident the
spectrogram's absorption band may be as a curve, there
still remain the problems of interpretation and of
identifying the peaks of those items which are vital
contributors to the odor. Analytical specification and
standardization by instrumentation are being studied
by the large essential oil manufacturers, by the National
Bureau of Standards, and by Sadtler Research Labora-
tories using punch-card methods to identify and sort the
large number of data available (SO).
Even though the senses of odor and taste are the
oldest senses, the most primary endowment of prehis-
toric man, research has not yet produced an analytical
classification similar to what we have for white light
in the spectrum and for sound in the musical scale.
D i e r e n t mixtures of various essential oils and aromatics
exhibit basically a similar odor. Literature reports
numerous olfactory researches (35-37) and theories
about the mechanism of olfactory stimulation based on
the chemical structural reactivity, volatility, molecular
vibration, etc. Quest,ionssuch as why similar odors are
produced by chemically different substances and why
concentration changes of the same chemical compound
a t times may produce opposite odor effects remain to be
answered.
Perhaps with new modern instruments and with new
research efforts we will be able to solve such problems,
as well as duplicate in a test tube the natural essential
oils, of which only very few can be successfully imitated
today. The study of essential oils and chemical
aromatics should prove most fruitful and stimulating
in the near future; many interesting problems await
solution.
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Volume 39, Number 5, May 1962 / 251