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Book Review Electronic Carges of Bonds in Organic Compounds. By G. V. Bykov translated from the Russian by J. T. Greaves edited by R. W

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Friedel-Crafts and Related Reactions. Edited by G . A . 01011.
Vol. 11: Alkylation and Related Reactions. Part I and
Part 11. Interscience Publishers, a Division of John Wiley
& Sons, New York-London-Sydney 1964. 1st Edit., Parts 1
and 2 together, 1362 pp., numerous tables, linen € 18.18.0
(about S 52.50).
Volume 1 of this series placed the general aspects of this
subject in the forefront, and now the discussion of “Alkylation and Related Reactions” is continued in greater detail.
The intense interest that has been shown by researchers -particularly in industrial laboratories - in the alkylation of
aromatics ever since its discovery by Friedel and Crufis has
resulted in such a vast amount of literature reports that the
subject can only be covered with great effort. The editor and
his co-authors are to be awarded high commendation for
undertaking the none too easy task of introducing an orderly
principle here. Scientific and patent literature is covered up
to 1961 - sometimes up to 1962 - and the-references cited
are mainly from publications that have appeared within
the past 15 years, although frequently (e.g. on pp. 2, 475, and
979) references are given to important reviews of earlier
investigations.
In Part 1, the following topics are discussed in sequence:
Methods of alkylating aromatics using alkenes and alkanes
(Chapter XIV, S. H. Putinkin and B. S. Friedman), using
dienes and substituted alkenes (Chapter XV, R. Koncos and
B. S. Friedman), using alkynes (Chapter XVI, V. Franzen),
using halogenated alkanes (Chapter XVII, F. A . D r h o w z a l ) ,
using alcohoIs and ethers (Chapter XVIiI, A . Schriesheim),
with aldehydes and ketones (Chapter XIX, J . E. Hofmun and
A . Schriesheim), and finally with inorganic esters and alkylarenesulfonates (Chapter XX, F. A. DruhowzaZ). Part 11
deals with halogenoalkylation (Chapter XXT, G . A . Oluh and
W. S. Tolgyesi), cycloalkylation of aromatics (Chapter XXII,
L. R . C . Barclay), dehydrogenative condensation (the Scholl
reaction, Chapter XXIII, A . 7‘. BaZuban and C . D . Nenitzescu),
isomerization of aromatic hydrocarbons (Chapter XXlV,
D . A . McCauZey), alkylation of saturated hydrocarbons
(Chapter XXV, L. Schmerling), the condensation of halogenoalkanes with alkenes and halogenoalkenes (Chapter XXVI,
L. Schmerling), the alkylation of alkenes with carbonyl
compounds (Chapter XXVII, C. W. Roberts), the isomerization of saturated hydrocarbons (Chapter XXVIII, H. Pines
and N . E. Hoflman), hydrogen exchange in aromatic compounds (Chapter XXIX, V. Gold),and polymerization (Chapter XXX, D . C. Pepper).
Both parts of Volume I1 are apparently intended for use
mainly as handbooks, for it has been attempted to reproduce
as much experimental material as possible in tabular form
(there are over 320 full-page tables) in order to enable the
reader t o acquire speedy information on the reaction he is
interested in. I n general, detailed theoretical considerations
such as appeared in large sections in Volume I and conferred
upon it the nature of a textbook have been disregarded here;
only a few are included, for example in Chapter XXIX
(hydrogen exchange) and Chapter XXX (polymerization;
here the Ziegler-Natta polymerization has been intentionally
excluded).
The outlay and appearance of the two books i s good. They
are intended primarily for the use of the experimenting
chemist, who, the reviewer earnestly believes, will soon find
that he would not like t o be without them.
J . Gosselrk
[NB 299/158 IE]
Electronic Charges of Bonds in Organic Compounds. By G. V.
Bykov, translated from the Russian by J. T. Creases,
edited by R. W. CZarke. Pergamon Press, Oxford-LondonNew York-Paris 1964. 1st Edit., viii 191 pp., 16 figs., 39
tables, linen €3.0.0 (about $8.25).
+
I n this monograph, where a summary of his publications appearing between 1951 and 1960 are presented, G . V. Bykov
attempts to develop a purely empirical treatment of the electronic structures of organic compounds. The starting point
178
for this approach is the linear relationship between the physical properties of a compound and the charge densities in
its bonds. The charge densities evaluated in this manner are
used to derive values for the electronegativity of the atoms,
this concept being defined in a new way. The author states
that the aim of this book is to coordinate the publications in
this field and t o make them available to all chemists. Unfortunately, this aim is not attained. Instead of relating the various - mostly quantum mechanical - theories of charge density t o one another the author’s theory is presented in such a n
unsystematic manner that it is difficult to distinguish between
the assumptions and the results of the theory.
The translation does not give a n account of the developments
that have taken place since the appearance of the Russian
edition and does not contribute to an easier understanding of
the text. By a slight stretch of imagination, it can be seen from
the context that “frequencies of valence fluctuations of the
CH-bonds”, for example, means C-H valence vibrational
frequencies and that “super-conjugation” means hyperconjugation. Since there are about a hundred errors spread out
evenly over the text and formulae, it is advisable to check all
derivations and formulae carefully. If the reader wishes t o
peruse some of the original literature cited, he will be surprised to learn that references to Pauling’s “Nature of the
Chemical Bond” and to Hiickel’s “Theoretische Grundlagen
der organischen Chemie” are based on the Russian editions
of these two books.
M. Klessinger [NB 2491107 IE]
Elimination Reactions. By D . V. Bunthorpe. Vol. 2 of a series:
Reaction Mechanisms in Organic Chemistry, edited by
E. D. Hughes. Elsevier Publishing Co., Amsterdam-London-New York 1963. 1st Edit., viii + 215 pp., 17 tables,
linen D M 25.- (about $6.30).
D . V. Banfhorpe has investigated elimination reactions, and
using his wide experience in this field has written this very
readable book. With its 482 references the work reflects the
state of this subject a t the beginning of 1962. The selection
and presentation of the material discussed illustrate the
author’s subjective approach, stressing the classical examples
of $-eliminations from saturated systems. Four sections are
devoted to a discussion of the mechanism of olefin formation,
the influence of structure o n the course of elimination redCtions, orientation rules and their interpretation, and elirninations from cyclic systems where base-catalysed reactions
are emphasized. Two chapters are devoted to acid-catalysed
and pyrolytic eliminations.
i t is well-nigh impossible to find a better presentation of this
subject matter; however, in the reviewer’s opinion, the standpoint adopted in the book is sometimes too “classical”, and
the chapter on “Less Usual Elimination Reactions” is too
short, even though references to reviews by other authors are
given. Thus, for example, eliminations from olefins are allowed
only three pages and fragmentations receive only two pages
of text. A little more space is allotted to a-eliminations, but
this certainly does not correspond nowadays to the importance to be attached to the mechanisms pertinent here. An
extended treatment of the latter and the inclusion of important results published after completion of the manuscripts
would be desirable in any subsequent edition of the work.
Nevertheless the book can be highly recommended to advanced students and to anyone interested in reaction mech-
anisms.
G . Kobrirh
[NB 255/113 IE]
Technique of Organic Chemistry, edited by A . Weissberger.
Vol. XI: Elucidation of Structures by Physical and Chemical Methods, Part IT. Edited by K . W. Bentley. Interscience
Publishers, a division of John Wiley & Sons, New YorkLondon 1963. 1st Edit. ix + 537 pp.. numerous tables, linen
€7.7.0 (about $20.00).
The second part of Vol. XI of this series contains ten interesting articles written by prominent organic chemists. 2.
Vulentu demonstrates in his article that distillation over zinc
Aiigew. Cheni. internat. Edif. / Vol. 4(1965)
No. 2
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