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Book Review Diazo Chemistry I. By H. Zollinger

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BOOKS
troscopy. which has advanced greatly in
the last ten years, based on the CPiMAS
method developed by Schaefer and
Stejskal. First M. J. Potrzebowski and J.
Michalski give a short introduction to this
field. Taking a bis(phosphory1)disulphide
as an cxamplc, they compare the information yielded by CP,'MAS measurements
with that given by X-ray crystallography,
and show correlations between the two
(e.g. Ah is correlated with the S-P-S
bond angle). I,. D. Quin describes how
electrophilic compounds containing phosphorus in Isw-coordination states, supported on silica gel, are used as scavengers
to prepare samples which are then analyzed bq CP:MAS 3 1 P N M R spectroscopy. This last chapter ends with an
introduction to MAS-frequency-dependent NMR spectroscopy by R. E. Wasylishcn. illustrated by results on
Cd(PPh.~)(N0.~)2.
The book a s a whole suffers from the
defects already mentioned earlier and
from those of conference reports in general. namely hcterogeneity across the chapters and ii relatively high price due to the
short print run. However. it is certainly
not redundant. since it collects together
for the first time the many analytical capabilities of ' * P N M R spectroscopy, which
can be used to investigate such widely different substances as highly reactive intermediates, nucleic acids, cyclotriphosphazenes. and derivatized coal constituents. The book can therefore be recommended not only for readers with interests in tlicse topics but for others too.
Ruiner Strtwhel
Institut fur Anorganische und
Analytische Chemie
der Technischen Universitat
Braunschweig (Germany)
Diazo Chemistry I. By H . Zollinger.
VCH
Verlagsgesellschaft,
Weinheim, 1994. 453 pp., hardcover
DM 198.00.-~-ISBN 3-527-2921 3-6
Heinrich Zollinger, the author of this
monograph on the chemistry of aromatic
and heteroaromatic diazo compounds. is
better qualified than virtually anyone else
to write a comprehensive and critical
work on the subject. Diazo compounds
are of great industrial importance. and
their chemistry raises difficult and
challenging problems. The work reviewed
here incorporates the knowledge gained
from the author's experience in the industrial application of diazonium compounds and in research into their
modes of reaction.
Its predecessors are
Zollinger's earlier
books Diazo and
Azo Chemistrj, of
Aliphatic und Arornatic Compounds
(1961) and Color
Cliemistr:), (1 987,
followed by a second edition in 1991). Part I1 of the present
work, covering aliphatic and inorganic diazonium compounds, is to be published
within a year following the first volume.
In thirteen chapters Diazo Chemistry I
deals with all the important concepts and
properties that make up the present understanding of the chemistry of aromatic
and heteroaromatic diazo compounds.
Chapter 1 (9 pp.) describes the historical
development of the subject and explains
the nomenclature for this group of compounds. Chapter 2 (31 pp.) deals with
preparative methods, beginning with the
most common procedure. the diazotization of amines by alkali metal nitrites in
dilute mineral acids. Aspects of diazotization in concentrated mineral acids and under anhydrous conditions are then discussed. The author also deals briefly with
the isolation of diazonium salts and draws
attention to the special case of the diazotization of aminophenols. which are readily deprotonated to give diazoketones.
Apart from the nitrosation of amines.
there are only a few other methods for
preparing diazonium salts, and this concludes the chapter. The third chapter
(25 pp.) is concerned with the kinetics and
mechanisms of diazotization. After critically reviewing the considerable literature
on this subject, the author devotes special
attention to the effects of different mineral acids and concentrations on the diazotization mechanism. Other aspects treated
include the use of nucleophilic catalysis in
diazotization, and the conversion of isolated N-nitrosamines to diazonium salts.
Chapter 4 (23 pp.) deals with the structurc
of diazonium salts, reviewing the latest results from crystal structure determinations. Spectroscopic observations and the
reactive properties of diazonium compounds are discussed and explained in the
light of theoretical studies. In Chapters 5
and 6 (48 pp. altogether) the author discusses the addition of nucleophiles to aryl-
diazonium compounds. The effect of pH
on the reaction of diazonium salts with
water is treated in detail. followed by discussions of the reactions with 0-,S-, N-,
P-. and C-nucleophiles. These two chapters are completed by a section on intramolecular coupling reactions, which
yield some interesting heterocyclic compounds. Chapter 7 (16 pp.) discusses the
mechanism of the addition of nucleophiles to diazonium ions and the structures of the resulting compounds. Mechanistic aspects of the reactions of
diazonium compounds involving loss of
nitrogen are treated in Chapter 9 (48 pp.).
and Chapter 10 (67 pp.) describes the synthetic applications of such reactions as a
general method for introducing nucleophiles into non-activated arenes. Chapter 11 (15 pp.) deals briefly with hostguest complexes of atene-diazonium
salts. then in Chapter 12 (78 pp.) the author treats what is undoubtedly the most
important reaction of aromatic and heterocyclic diazonium compounds, the coupling reaction yielding a/o dyes. The last
chapter (19 pp.) is concerned with the formation and reactions of triazenes.
The author's comprehensive knowledge
of aromatic and heteroaromatic diazoniuni compounds has resulted in a monograph which contains practically all the
information that a specialist working in
this field could wish for. The reader approaching the subject from a somewhat
greater distance may find that the often
very detailed treatment presents a rather
formidable "energy barrier". Also many
of the formula schemes are not very carefully prepared. in stark contrast to the
precision of the text. As well as many
errors of stoichiometry. the most serious
problem is that in many c ~ s e sinsufficient
care has been taken with the layout of the
formulas. Better formula schemes presenting the information clearly would
have greatly improved the book. especially for the non-specialist.
However, every chemist whose work is
concerned with diazonium compounds,
whether in industry or academia. will find
this book indispensabic. Furthermore,
those whose research intrrests lie in other
directions but who occasionally have to
deal with diazonium compounds. especially in a teaching role, should certainly
use this book at such times.
6 i . n ~Ei/;irnhergrr
Institut fur Organische Chemie
und Isotopenforschung
der Universitiit Sturtgart (Germany)
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