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Book Review Houben-Weyl Methoden der organischen Chemie (Houben-Weyl Methods of Organic Chemistry). Vol

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BOOK REVIEWS
Houben-Weyl: Methoden der organischen Chemie (HoubenWeyl: Methods of Organic Chemistry). Vol. 10, Part 3
“Stickstoffverbindungen 1/3” (“Nitrogen Compounds
I/3”). Georg Thieme Verlag, Stuttgart 1965. 4th Edit.,
edited by Eugen Miiller. xLiii + 971 pp., 69 tables,
subscription price before publication of the last volume
D M 229.50 (about $ 5 7 . ~ ) . Single volumes D M 255.about $63.-).
The new edition of Houben-Weyl, having treated amines and
quaternary ammonium compounds in volume 1111-3,
allots three volumes to the remaining nitrogen compounds,
the third of these now being the first to appear. In this the
well-tried method of presentation is used for the preparation
and reactions of compounds containing multiply bonded
nitrogen attached to at least one aromatic residue. The
individual sections, except for the two chapters o n azides
and nitrile oxides (see below), are written by Industrial
chemists (Farbenfabriken Bayer) whose experience guarantees reliable reporting. It should, however, be emphasized
that general scientific importance attaches to the azo compounds treated, as i s particularly clear in the content and
style of chapters 1, 4, and 5. In all sections the literature of
the past 80 (!) years (modern authors please note) is carefully
evaluated and it is good to see that this continues up to 1964.
1. Aromatic Diazonium Salts (200 pp., 35 tables, R . Putter).
This chapter conveys a lively impression of the numerous
reactions available for the preparation of diazonium salts
and of the influence of conditions and substituents. It
includes heterocyclic diazonium salts. Direct introduction
of the diazonium group, oxidation of arylbydrazines, and
use of amine derivatives are described as well as methods of
diazotization. Reactions involving loss of nitrogen are also
described extensively. The article is enriched by inclusion
of the most important theoretical results and of numerous
tables.
2. Diary1 Azo Compounds (244 pp., 2 tables, K . H . Schundehiitte). This unusually extensive field is made clear by means
of skillfully chosen examples. First the tautomerism of
hydroxy- and amino-azo compounds is described, and then
the various coupling reactions of diazonium salts with hydrocarbons, derivatives of aromatic amines and phenols,
reactions affording polyazo compounds, and the preparation
of macromolecular azo compounds. Here one also finds
reactions that are seldom considered, such as the Cu9catalysed conversion 2 ArNz9 + Ar-N=N-Ar
N2 (Vor[under), as well as the preparation of azo compounds from
reactive methylene compounds or pheilols and active azides,
and oxidative coupling. The section on alkylation and acylation of amino-azo compounds includes the preparation of
reactive dyestuffs. The numerous methods for preparation
of metal complexes of azo dyes occupy 22 pages. This
chapter will appeal particularly to the technologically
oriented chemist, not least because the patent literature is
extensively evaluated.
3. Aromatic-Aliphatic Azo and Azoxy Compounds from
Arylhydrazones by Coupling (73 pp., 6 tables, E. Enders).
This scientifically interesting chapter describes the oxidative
conversion of hydrazones into azo compounds, also their
coupling with reactive methylene compounds (Japp-Klingemann reaction). Other relevant methods are also considered.
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4. Other Arylazo Compounds (72 pp., 8 tables, R . Putter).
Under this heading are collected arene-diazotates, -diazo
ethers, -diazosulfonates, -diazosulfones, -diazocarboxylates,
etc. The original literature about this many-sided group of
compounds, that is so troublesome to read, is here explained
by means of characteristic examples.
5. Formazans (33 pp., 2 tables, R . Putter). This class of
compounds has long been known, but it has recently gained
importance owing to the reversible conversion into tetra-
528
zolium sAts and stable radicals. Views on the mechanism of
the syntheses are critically examined.
6. Aromatic Triazenes and Higher Azo Homologues (44 pp.,
8 tables, C . Siiling). Aromatic-aliphatic as well as purely
aromatic triazenes can be singled out on account of their
technical importance as “protected” diazonium salts, and
on account of the acid-catalysed fission. Surprisingly,
triazatrimethinecyanines also occur in this section. Tetrazenes and pentazadienes are also treated.
7. Aromatic AZOXYCompounds (26 pp., 1 table, K . H .
Schiindehiitte). This section describes the constitutional
problem and then the synthesis from aromatic nitroso and
hydroxyamino compounds, by reduction of nitro compounds,
and by oxidation of azo compounds. Particular interest
attaches to the Wallach rearrangement of azoxy compounds
which takes different courses in light and in sulfuric acid.
The last two chapters depart from the form of the previous
ones. C. Griindmunn gives a n excellent exposition of the
importance of two functional groups in the whole field of
organic chemistry:
8. Organic Azides (54 pp.. 4 tables). First the preparation
of hydrazoic acid and its salts is described and then introduction of the azido group into organic compounds by addition
and substitution as well as by reactions of other nitrogencontaining groups. The reactions of azido compounds are of
general importance: addition to multiple bonds, the Schmidt
and the Curtius degradation, and the mode of reaction
(described In detail) of the nitrenes that occur as intermediates.
9. Nitrile Oxides (29 pp., 3 tables). The very instructive
description of this class of compounds, to which little attention is usually paid, includes not merely their prcparation
(with a review in tabular form) but also particularly their
very numerous addition reactions to multiple bonds that
lead, e.g., to furoxans and isoxazole derivatives. This and
the preceding chapter end with methods of detection of the
two groups.
This short indication of content must suffice to show that
this volume maintains the high standard of the complete
work. In accordance with its aims the methodological aspect
is in the foreground, and the experimental detail is intended
as a help for analogous experiments.
The volume ends with an exhaustive author (42 pp.) and
subject index (38 pp.), to which is added a special index of
diazonium salts and the azo compounds treated (arranged
according to their methods of preparation). A patent index
would in this case have been useful.
A proposal for future volumes: preparative yields should be
restricted to whole units percent. The extensive list of journals (37 pp.) would be better placed at the end, with the
iablc of abiircviations on “fold-out” pages.
S. Hiirriz
[NB 479 333 1EI
Klassische und molekulare Genetik (Classical and Molecular
Genetics). By C . Bresch. Springer-Verlag, Berlin-Gottingen-Heidelberg 1964. 1st Edit., viii 319 pp., numerous
figs., 14 tables, cardboard D M 32.- (cu. $ 8.-).
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Publication of this book is most welcome. The central position
of genetics in biology, already recognized by far-sighted investigators at the turn of the century, is nowadays clearly
acknowledged.
C. Eresch, the author of the present book is a representative
of the modcrn “molecular” biologists; he came to biology
through physics. He has reviewed the total content of moleAirgew. Chem.
internot. Edit. / Vol. 5 (1966) / No. 5
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