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Book Review The Chemistry of Enols. (Series The Chemistry of Functional Groups; Series editor S. Patai). Volume editor Z. Rappoport

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ed by a large number of illustrative figures, energy-level diagrams, numerous references and cross references, and extensive author and subject indexes. The book presents basic
physical concepts in simple terms with little formalism and
numerous experimental examples not easily found elsewhere
in such breadth. As such, it provides an interesting and comprehensible introduction for the newcomer to this fascinating field and a valuable source of information for the specialist. However, the readership the book deserves could be
limited by its prohibitive price.
Hans Heitele
Institut fur Physikalische und Theoretische Chemie
der Technischen Universitat Miinchen,
Garching (FRG)
The Chemistry of Enols. (Series: The Chemistry of Functional Groups; Series editor: s.Patai). Volume editor: Z . Rappoport. Wiley, Chichester, 1990. xvi, 823 pp., hardcover
€ 195.00.-ISBN 0-471-91720-6
The addition to the Patai series of a volume treating enols
as a functional group in its own right is clearly warranted by
the revolutionary recent advances achieved in the direct
investigation of enol chemistry. The editor of this volume
has succeeded in engaging leading proponents of recent
developments, thus providing a highly competent and informative account of all the aspects usually covered in the series, namely preparation, structure, and reactivity. Personal
views given by the individual authors provide a vivid presentation of a lively research area from different standpoints. As
a consequence, there is some reiteration of material in different chapters, but, overall, the editor and authors have
achieved a consistent and comprehensive presentation of the
chemistry of enols. Literature coverage is up to 1988 (in part
1989)and contains nearly 2500 references as well as extensive
author and subject indexes providing easy access to up-todate information. A majority of the references cited are from
the last decade, but important early work starting from
Erlenmeyer’s first contribution to enol chemistry in 1875 is
also included. The chemistry of enolates and enol ethers is
deliberately excluded.
Chapter 1 on “Theoretical Calculations” by Y Apeloig
provides an exemplary description of the fruitful interactions
between state-of-the-art theoretical methods and current experimental research. In Chapter 2 J. P. Guthrie derives increments for the Benson group additivity scheme from the
presently available data, and shows how reliably these allow
one to estimate thermodynamic parameters of enols. Chapter 3, “The Chemistry of Ionized Enols in the Gas Phase” by
F. TureEek, discusses the reversal of keto-enol equilibria in
radical cations. In Chapter 4 on “NMR, IR, Conformation
and Hydrogen Bonding” by B. Floris the emphasis is on
systems with substantial equilibrium concentrations of two
or more tautomers; the chapter includes a comprehensive
compilation of spectral data as well as studies of the effects
of solvent, substituents and temperature on equilibria. In
Chapter 5 methods for generating unstable enols in pure
form or in higher than equilibrium concentrations are presented by B. Capon. In Chapter 6 reliable keto-enol equilibrium constants are compiled by J. Toullec, and the merits
and limitations of various methods for determining these
data are critically reviewed. Old and new insight into the
kinetics and mechanism of enolization and ketonization is
reviewed by J. R. Keefe and A. J. Kresge (Chapter 7). Ernphasis is laid on new developments in monitoring ketonizaAngew. Chem. Inl. Ed. Engl. 31 (1992) No.1
tion reactions in aqueous solution, general-acid and generalbase catalysis, isotope effects, and the pathways of the “uncatalyzed” reactions in protic solvents. Isolable and relatively stable simple enols are discussed by H. Hart, Z.
Rappoport and S. E. Biali in Chapter 8. As “simple” enols
they consider those lacking stabilizing functional groups
such as CO in the P-position, in particular the kinetically
stabilized aryl-substituted enols of the type studied by Fuson
in the early forties. Chapter 9 on “Photochemical Reactions
Involving Enols” by A. C. Weedon covers the numerous reactions which lead to the formation of enols as primary
products, as well as the photoreactions of enols themselves.
In Chapter 10 the scarce experimental data on enols of carboxylic acids and esters are reviewed by A. F. Hegarty and P.
O’Neill. In “The Biochemistry of Enols” (Chapter 11) J. P.
Richard focusses on the biochemical reactions of carbonyl
compounds which proceed through enol or enolate reaction intermediates, excluding reactions of the stable enol
Vitamin C. Unstable tautomers can sometimes be stabilized
by complexation; the properties of transition metal-enol
complexes are covered by D. Milstein in Chapter 12
“Organometallic Chemistry of Enols”. Experimental data
on “Structural Chemistry”, mainly from single crystal X-ray
measurements on isolable enols, are compiled and discussed
by G. Gilli and V. Bertolasi in Chapter 13.
The Patai series needs no recommendation as an indispensable source of comprehensive, critical and up-to-date
information. It is clearly a must for any chemical library.
Unfortunately this situation is being exploited by the publishers: the astronomical price of this volume will discourage
most researchers from purchasing their own copy.
Jakob Wirz
Institut fur Physikalische Chemie
der Universitat Base1 (Switzerland)
Synthesis of Lanthanide and Actinide Compounds. Edited by
G. Meyer and L. R. Morss. Kluwer Academic Publishers,
Dordrecht, 1991. xvi, 367 pp., hardcover HFI 220.00.ISBN 0-7923-1018-7
This compendium of invited reviews is the second in a
series of “Topics in $Element Chemistry” edited by Shyama
P. Shinha, the first having appeared some six years ago,
entitled “Americium and Curium Chemistry and Technology”, edited by Edelstein, Navratil, and Schulz. Meyer and
Morss have assembled an outstanding array of contributions
from several of the more noteworthy contemporaries in the
area of synthesis off-element compounds. As they observe in
their Preface, “The history of the rare earths has entered its
third century ;transuranium elements are now a half century
old”, so we cannot expect contributions from all ofthe major
players in f-element chemistry. The fourteen contributions
do, however, contain over 1400 citations that do well to encompass much of the previous work. The goal of the editors
and authors to compile a review of “tried and true” synthetic
techniques has been achieved. Since no single volume of
synthetic reviews can ever be complete, we should anxiously
await the next volume. What follows are some brief comments on each of the fourteen sections.
John Haschke of Rockwell International presents a very
detailed synopsis of Actinide Hydride synthesis in which he
includes an extensive review of kinetics. An additional section concerning the safe handling of hydrides and reduced
actinides was a welcome sight. So often in the literature we
neglect the “obvious” safety concerns. A very detailed sec-
Verlugsgesellschuft mbH, W-6940 Weinheim. 1992
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