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Book Review The Chemistry of Functional Groups. The Chemistry of Diazonium and Diazo Groups. Edited by S. Patai

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and E2 reactions are discussed, where frequently specific solvations decide the issue. However, this chapter also includes
a thorough discussion of the considerably weaker effects in
radical and pericyclic reactions, together with their mechanistic consequences. The chapter has 45 1 references.
A further chapter (45 pages) deals with solvent effects on
spectral properties. Starting with solvatochromism phenomena (UV/VIS), the author describes effects on IR, NMR,
and ESR spectra, by which it is also often possible to detect
specific solvations. This provides a logical transition to linear
“free energy relationships” (54 pages), which are mainly derived from spectroscopic data for given model systems and
which, possibly just because of their empirical nature, range
over an astonishingly wide field of chemical reactivity. Here
too the book shows the use and limitations of the Z and ET
values and AN and D N values, together with the value of
multiparametric equations, some of which have only recently
been developed.
An appendix gives brief information about the purification and possible applications of solvents, their spectroscopic
and other physical data, and also their toxicity.
No other work currently available presents the confusing
multiplicity of solvent effects as thoroughly, comprehensively, and critically as this one. Furthermore, it is intended for
the organic chemist who wants to interpret these effects or to
use them in planning his reactions. It is hoped that the high
price will not hinder a wide readership of this book.
Siegfried Hiinig [NB 481 IE]
Organometallic Mechanisms and Catalysis. By J. K. Kochi.
Academic Press, New York 1978. xvii, 623 pp., $ 59.50.
It isn’t very often that a reviewer has the good luck to be
asked to write a critique about a book which he intended to
purchase and I was, therefore, delighted when this volume
landed on my desk-particularly in view of the price.
Organometallic chemistry and homogeneous catalysis can
no longer be ignored by conventional organic and inorganic
chemists: many organometallic compounds have either
found direct practical application (e. g. organotin- and organolead compounds) or are routinely used as stoichiometric
reagents in organic synthesis (e.g. organolithium- and organomagnesium compounds) or are involved as intermediates
in metal catalyzed organic transformations some of which
now form the basis of large industrial processes (e.g. organocobalt- and organonickel compounds in the hydroformylation and hydrocyanation of alkenes).
Although a number of reaction- or metal-specific books
and reviews are available, it has become clear in the last few
years that the role of organometallic species in organic synthesis could be profitably discussed from a unifying mechanistic standpoint and it is to fill this need that this book has
been written.
Has the author succeeded? On the whole I think he has.
He is certainly to be admired for not capitulating before the
sheer volume of the material to be discussed. The book is divided into three related sections: part one deals with oxidation-reduction processes in which the metal undergoes a discrete change in oxidation state, part two is devoted to the
chemistry of organometallic compounds with emphasis on
reactions leading to cleavage of the metal-carbon bond, and
part three is concerned with charge transfer interactions.
This arrangement enables a surprising amount of information to be classified while avoiding the frequently artificial
distincticn between main group- and transition-metal organometallic compounds. A first-class index makes it easy to
804
find relevant material. The main difficulty facing the author
is that concrete evidence is often lacking for many of the catalytic processes being considered and, in spite of his good
intentions, the discussion all too often becomes metalspecific and generalizations have to be followed by a disclaimer. The most desirable effect which this book could have
would be to stimulate further work towards greater mechanistic uniformity.
The book will be of greatest interest to chemists involved
directly with organometallic compounds and catalysis but it
should also be very profitable reading for all preparative organic chemists. Its greatest service will be to act as an orientation point in classifying new information. For me at least it
will now be easier to keep an eye on what is happening in the
wood while at the same time tending some of the trees.
P. W . Jolly [NB 477 IE]
The Chemistry of Functional Groups. The Chemistry of Diazonium and Diazo Groups. Edited by S. Patai. John Wiley
& Sons, New York 1978. Part 1, xiv, 510 pp.; Part 2, xiv,
pp. 511-1069; bound, together $ 130.00.
The last comprehensive survey of diazo and diazonium
compounds (H. Zollinger: Diazo and Azo Chemistry) was
published in 1961; the pertinent chapters of Houben-Weyl
(10/3 and 10/4) were written in 1965 and 1968. The present
two-volume work in the series “Chemistry of Functional
Groups” is therefore most welcome.
Diazonium ions and diazo compounds do have a number
of interfaces (they are related by acid-base equilibria in the
aliphatic series), but differ greatly in their reactions. The two
classes of compounds are therefore considered together in
some of the chapters, but separately in others. The work
opens with a theoretical survey ( J . B. MoJfaat)which also embraces diazirines and diimides. Three chapters are concerned
with the synthesis of diazonium salts (14, K. Schank) and of
diazoalkanes and their carbonyl, phosphoryl, and sulfonyl
derivatives (15, 17, M. Regitz). Further chapters are devoted
to acid-base equilibria (2, V. Sthba; 6, J. F. McGarrity),
structural problems (3, S. Sorriso; 7, H. M . Niemeyer), and
analytical procedures (5, D. A. Ben-Efraim). The section on
thermochemistry (4, R. Shaw) does not appear very successful, being based on a value for the heat of formation of diazomethane which is most probably incorrect. Mechanistic
questions are discussed with particular emphasis on photochemistry (9, W. Ando), electrochemistry (10, J. Fry), substituent effects (11, E. S. Lewis), kinetics (12, A . F. Hegarty),
rearrangements (13, D. Whittaker), and the use of isotopes
(16, P. J. Smith and K . C. Westaway).Special attention is focused on the synthetic application of diazonium salts (8, D.
S. Wulfman) and diazo compounds (18, D. S. Wulfman, G.
Linstumelle, and C. F. Cooper) by two large chapters with ca.
2400 references. This is where the chemist engaged in preparative work will gain well-founded information and critical
suggestions concerning, for example, the choice of catalyst in
the decomposition of diazo compounds.
Repetition is bound to occur in a book written by 19 authors
(e.g. the Wolff rearrangement is mentioned in Chapters 3, 9,
13, and 18); and yet new aspects are often revealed precisely
by such repetition. Some information turns up in unexpected
places, e. g. I3C-NMR data of diazo compounds in Chapters
11 and 16, but not in Chapter 5 and regrettably not in the index. Typographical errors are rare (e.g. pp. 374, 413, 607,
629, 726, 851, 855, 909,932); errors of fact are even rarer (the
statement on p. 13 that diazirine is more stable than diazomethane contradicts the heats of formation compiled in Tables
10 and 11; classification of the photochemical Bamford-StevAngew. Chem. Int. Ed. En@. I8 (1Y79) No. 1 0
ens reaction as “photolysis of aliphatic diazonium ions” in
Chapter 9 is surprising; the hypothesis of “hot” cations is attributed to the wrong authors on p. 574). Interspersion of an
occasional bon mot provides amusement between formulae
and tables: “It is not clear whether the catalyst plays an active role or represents a retreat to the chemistry of (Paracelsus) von Hohenheim” (p. 910). The subject index (24 pages)
is comparatively exhaustive; the author index (66 pages) provides a visible measure of the relative ranking of the pundits
(Regilt is a clear winner with 11.8 cm).
The high quality of most of the contributions, the high information content, and the careful editing recommend these
volumes not only to subscribers to the series but to a wide
circle of organic chemists engaged in mechanistic and preparative work.
WoIfgang Kirmse [NB 475 IE]
IUPAC: Carbohydrate Chemistry-9 (London 1978). Edited
by A. B. Foster. Pergamon Press, New York 1979. pp.
1343-1476, bound, $ 30.80.--ISBN 0-08-022354-0
Advances in Structure Research by Diffraction Methods,
Vol. 7. Unconventional Microscopy for Molecular Structure Determination. Edited by W . Hoppe and R. Mason.
Vieweg & Sohn, Braunschweig 1979. 225 pp., bound, DM
84.00.-ISBN 3-528-08117-1
Developments in Polymerisation-2. Edited by R. N. Haward. Applied Science Publ., London 1979. xi, 285 pp..
bound, $ 62.50.-ISBN 0-85334-821-9
Chemistry and Physics of Carbon, Vol. 15. Edited by Ph. L.
Walker, Jr. and P. A . Thrower. Marcel Dekker, Basel 1979.
xi, 299 pp., bound, SFrs. 82.00.-ISBN 0-8247-6816-7
Handbuch zur Anwendung der Nomenklatur organischchemischer Verbindungen. Edited by W. Liebscher. Akademie-Verlag, Berlin 1979. xix, 1076 S., bound, ca. DM
135.OO.
Air Pollution Chemistry. By J. D. Butler. Academic Press,
New York 1979. viii, 408 pp., bound, $52.50.-ISBN 0-12147950-1
Chemie der organischen Derivate des Hydrazins. By B. V.
Zoffe, M. A . Kuznecou, and A . A . Potechin. Verlag Chimija,
Leningrad 1979. 224 pp., paper 1 Rubel, 90 Kop.
Amino-acids, Peptides and Proteins, Vol. 10. Senior Reporter: R. C. Sheppard. The Chemical Society, London 1979.
xix, 537 pp., bound, DM 155.00.--ISBN 0-85186-094-X.A volume of the series “Specialist Periodical Reports”
A Theory of Biochemical Supersystems and its Application
to Problems of Natural and Artificial Biogenesis. By T.
Ganti. Akademiai Kiado, Budapest 1979. 136 pp., paperback.-ISBN 963-05-1719-1
Spektren und Strukturen organischer Verbindungen. By E.
Fahr and M . Mitschke. “taschentext” 61. Verlag Chemie/
Physik-Verlag, Weinheim 1979. 130 pp., paper, DM
24.80.-ISBN 3-527-21027-X
Carbon-13 NMR Spectral Data. A “Living” COM-Microfiche Collection of Reference Material. Edited by W.
Bremser, L. Ernst, B. Franke, R. Gerhards, and A . Hardt.
Verlag Chemie, Weinheim 1979. 2nd edit. 32 pp., 108 microfiches with 18719 spectra of 14786 compound. Looseleaf file, DM 1lOO.OO.-ISBN 3-527-25835-3
Umweltforschungsreport 1977/78. Issued by the Umweltbundesamt Berlin. 233 pp., paper.
Landolt-Bornstein. Zahlenwerte und Funktionen aus Naturwissenschaft und Technik. Neue Serie. Gruppe 111,
Band 7. Edited by K. H. Hellwege and A. M. Hellwege.
Springer-Verlag, Berlin 1979. xxvii, 452 pp., bound, DM
550.00.-ISBN 3-540-09039-8
Atom-Molecule Collision Theory. Edited by R. B. Bernstein.
Plenum Press, New York 1979. xx, 779 pp., bound, $
57.50.-ISBN 0-306-40121-5
Chemical Engineering, Vol. 5. By J. M. Coulson and J. E
Richardson. Solutions to the Problems in Chemical Engineering, Vol. 2. By J. B. Backhurst and J. H. Harker. Pergamon Press, New York 1979. vii, 255 pp., paper, $
15.00.--ISBN 0-08-022952-2
Fluid Catalytic Cracking with Zeolite Catalysts. By J. B. Venuto and E. T. Habib, Jr. Marcel Dekker, Basel 1979. vi,
156 pp., bound, SFrs. 44.00.-ISBN 0-8247-6870-1
Angeu,. Chem. In!. Ed. Engl. I R (1979)
No. 10
Gas Phase Ion Chemistry, Vol. 1. Edited by M. T. Bowers.
Academic Press, New York 1979. xiii, 354 pp., bound, $
39.50.--ISBN 0-12-120801-X
The Porphyrins, Vol. 7. Biochemistry, Part B. Edited by D.
Dolphin. Academic Press, New York 1979. xxi, 550 pp.,
bound, $ 55.00.--ISBN 0-12-220107-8
The Chemistry of Heterocyclic Compounds, Vol. 25. Indoles,
Part 3. Edited by W. J. Houlihan. John Wiley & Sons,
New York 1979. x, 586 pp., bound, $ 93.00-ISBN 0-47105132-2
Porphyrin Chemistry Advances. Edited by F. R. Longo. Ann
Arbor Science Publ., Ann Arbor 1979. vii, 368 pp., bound,
€ 18.70.--ISBN 0-250-40229-7
Studienbucher Chemie: Einfuhrung in die Kunststoffchemie.
By G. Rink. Diesterweg/Salle/Sauerlander, Frankfurt
1979. x, 210 pp., paper, DM 14.90.--ISBN 3-7941-1468-X
Liquid Chromatographic Analysis of Food and Beverages,
Vol. 2. Edited by G. Charalambous. Academic Press, New
York 1979. xi, pp. 237-563, bound, $ 25.00.--ISBN 0-12169002-4
805
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