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Book Review Advances in Heterocyclic Chemistry. Vol. 5. Edited by A. R. Katrizky A. J. Boulton and J. M

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Advances in Heterocyclic Chemistry. Vol. 5. Edited by A . R.
Katritzky, A . J. Boulton, and J. M. Lagowski; Academic
Press, New York-London 1965. 1st ed., xiv, 395 pp.,
395 illustrations, $16.00.
In the first article (67 pp.), R. Zahradnik deals with theoretical
considerations on the electronic structure, the resulting
reactivity, and a number of physical properties of heterocyclic
sulfur compounds. Starting with the model for the atomic
orbitals of sulfur, calculations of the molecular orbitals for
sulfur compounds are presented, and comparisons are drawn
with corresponding carbocycles.
The second article (49 pp.) by K. Zahradnik and J . Koutecki.
covers theoretical studies on the physical properties and
reactivity of nitrogen heterocycles (“azines”). This article
presents lucidly a tabular collection of spectral data, polarographic half-wave potentials, Tc-electron densities, basicities,
and chemical reactivities of mono-aza heterocycles with a
completeness that is unequalled elsewhere.
F. Kurrer is responsible for the article o n 1,2,3-thiadiazoles
(85 pp.), a class of substances that has been closely studied
only in the last ten years. The syntheses developed during
this time are described, those discovered by J . Goerdeler being
particularly outstanding. Other chapters deal with the
chemical and physical as well as physiological and pharmacological properties of these compounds.
R . A . Heacock wrote the article on aminochromes (85 pp.),
the deep-red to violet oxidation products of 3,4-dihydroxyphenylethylamine and its derivatives (dopa amines). The
possibilities of formation, the methods of preparation, and
the mechanism of formation are discussed. The physical
behavior, and especially chromatographic and spectral data,
are presented clearly. The chemical properties, stability, and
rearrangement and condensation reactions are described at
length. Detailed reference is also made to the importance of
the aminochromes in medicine and biology, particularly for
the formation of melanine in the dark pigments or the
adrenochrome metabolism.
B. S . Thygarajan discusses the aromatic quinolizines (23 pp.).
He describes in detail the syntheses of the known quinolizine
derivatives, the possible reactions, and the ultraviolet and
infrared spectra.
The last contribution (50 pp.) by N . Kochetkov and A . M .
Likhosherstov, presents a digest of 125 original publications
o n advances in pyrrolizidine chemistry. The syntheses
described are backed up by numerous clear formulae. One
chapter is devoted to the reIative and absolute configuration
and stereochemical transformations of the pyrrolizidine
bases. The reactions and ring cleavages are reported at
length. The section closes with a discussion of the biogenesis
of naturally-occurring pyrrolizidines from ornithine or phydroxyornithine.
The book contains a balanced blend of theoretical and
preparative results from research o n special heterocycles.
The layout of the book is again outstanding, so that it is a
worthy successor to the earlier volumes, and will be a useful
source of information for anyone who is interested in heterocycles.
W. Ried
LNB 530 IE]
Comprehensive Biochemistry. Edited by M . Florkin and E. H .
Stotz. Vol. 16: Hydrolytic Reactions; Cobamide and Biotin Coenzymes 111. Elsevier Publishing Company, Amsterdam-London-New York 1965. 1st ed. XII, 267 pp. 10 illustrations, 37.50 Dutch florins (by subscription, 30.00 Dfl.).
Of the many reactions of enzymes a few are selected as examples and treated here in exemplary fashion; these are the
reactions of the hydrolases, the action of which as acid-base
catalysts has been largely elucidated in recent years, and
those of the isomerizing and carboxylating enzymes that use
cobamides and biotin as cofactors. A deeper insight into the
arrangement of the active site of esterases has been obtained,
mainly by variation of the structure of the substrate and by
Angew. Chem. internat. Edit. 1 Vol. 6 (1967)
No. 2
means of inhibitors; this is discussed by Oosterbaan and
Jnnsz. The role of phosphatases in the synthesis and degradation of cell substances is described by Morfon (in a n article
published posthumously) with his usual lucidity. A particularly topical section which, like the others, contains interesting aspects based on the personal experience of the author
(Cunnigham), deals with the serine proteases. Considerable
space in this section is devoted to the views on the formation
of active enzyme-substrate complexes, which have already
been extended to other enzyme mechanisms, and the chemical
and physical principles underlying these ideas are discussed.
The chapter on the cobamide (BIZ)coenzymes, in which the
essentials are presented concisely and authoritatively by
Weisbach, Peterkofsky, and Barker, is a masterpiece of selective writing. A somewhat less balanced section is that on
biotin carboxylases by Ochoa and Kaziro However, the discussion also includes a11 the necessary detail.
This volume is again undoubtedly well presented. However,
consideration of the further progress of the enterprise raises
the question of whether the completeness of this work, for
which a high price must be paid, is not a luxury. The volumes
should not be included in a single treatise, where there is
always a desire to complete the series, but which will nevertheless not become a comprehensive manual of biochemistry;
they should instead have been published as monographs,
from which one could select those required, and which could
be more easily kept up-to-date by publication of new editions.
L . Jaenicke
[NB 539 I€]
[l] Cf. Angew. Chem. 76, 868 (1964).
Advances in Organic Chemistry. Methods and Results. Vol. 5 .
Edited by R . A. Raphael, E. C . Taylor, and H. Wynberg.
John Wiley & Sons. Ltd., New York-London-Sydney 1965.
1 s t Edit.,vii, 337pp., several figures and tables, cloth, 105s.
In volume 5 [*I of “Advances in Organic Chemistry”, A . J .
Parker reports on the use of dipolar aprotic solvents, R .
McCrindle and K . H. Overton on the chemistry of cyclic dlterpenoids, and M. Tic@ o n the determination of intramolecular hydrogen bonds by I R spectroscopy and the application
of such data to stereochemistry.
Parker’s article (46 pp.; 232 references, of which no. 232
appears in the list of references but not in the text) is a careless piece of work and contains many mistakes. The content
of the publications on which the article is based is reviewed
(often distortedly) in a loose sequence instead of coordinated
to form a unified picture. Consequently, there is considerable
repetition with different references, while other topics are
discussed in unsuitable places (e.g. the reaction of mercaptides with oxygen appears under “Dipolar Aprotic Solvents
as Reactants”, and the formation of alkyl nitrates is given as
a n example of the reaction R X R’zNo+ NRR’;! X”);
with the result that the original sense is often lost (e.g. p. 27:
preparation of nylon from isocyanates). The main value of
this article would therefore lie in the reference list, but for its
careless compilation: 60 references are incorrect, data o n
the publishers rudimentary (e.g. Elsevier, New York’‘),
abbreviations of journals are sometimes inconsistent and
journals that are translated into English are referred to only
as the English translation. The work cited occasionally does
not deal with the topic in connection with which it is referred
McCrindle and Overton review 231 papers in 67 pages. The
terse discussion does not always follow Fieser’s “Style Guide
for Chemists”, and occasional incorrect (e.g. p. 74 under the
chemistry of dihydrorosenonolactone, p. 51, two methyl
groups missing; note a) of Tables I to IV is not relevant) or
incomprehensible presentation (p. 80, formula of podototarin) makes it necessary to consult the original literature (spot checks indicate that the references are almost free
from errors). The use of unaccustomed abbreviations is not
conducive to easy reading.
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