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Book Review Synthetic Fluorine Chemistry. Edited by G. A. Olah R. D. Chambers and G. K

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A little help is provided by the brief subject index; otherwise
the reader has to consult the original literature.
Nobody expects a book free of errors, and one can disregard misprints such as the resonance arrow for the Menschutkin reaction on page 1. More annoying is the use of
different letters to describe the same property, for example,
.d on pages 136-7, but a three pages later. On account of
the profusion of newly introduced symbols, this is very disturbing.
Whether the considerable time spent in understanding the
mathematics and terminology of this model pays off for the
“common” chemist, in order to describe experimental data
semi-quantitatively with a better theoretical basis, may be
left to his or her own discretion. The specialist familiar with
the authors’ original publications will probably not discover
much new material. Most of the diagrams in this book have
also been taken from the primary literature, sometimes in
severely reduced form which makes them difficult to decipher.
To conclude: this book was meant to serve many, but
turns out to be superficial in many aspects. Apart from the
discussion about the quantitative validity of the model, the
form of the book means that it will probably be useful to few
other than specialists.
J: Jens Woqf
Organisch-Chemisches Institut
der Universitat Heidelberg (FRG)
Synthetic Fluorine Chemistry. Edited by G. A . Olah, R. D.
Chambers and G. K. Surya Prakash. Wiley, New York,
1992. XVII, 402 pp., hardcover 5 75.00.-ISBN 0-47154370-5
The properties of fluorine, both as an element and in its
compounds, differ so markedly from those of the other halogens that fluorine chemistry has developed as a distinct subject with its own special methods. Now, 106 years after elemental fluorine was first obtained, this branch of chemistry
has become so extensive that to review it all is scarcely possible, even for an expert in the field. Accordingly, the aim of
this book is not to present a systematic survey; instead it
consists of 17 chapters in which leading scientists from universities and industry give comprehensive reviews of selected
areas of inorganic and, more especially, organic fluorine
chemistry. The book is based on papers presented at a symposium on Synthetic Fluorine Chemistry, which was organized by the Loker Hydrocarbon Research Institute of the
University of Southern California in February 1990.
In Chapter 1 Schrobilgen describes the preparation and
Lewis acid behavior of noble gas fluoride cations. Christe,
Wilson, and Schack (Ch. 2) describe methods for replacing
fluorine by oxygen in fluorides and oxyfluorides. Aubke,
Cader, and Mistry (Ch. 3) present a comprehensive review of
transition metal derivatives of strong protonic acids and superacids. Seppelt (Ch. 4)describes the preparation and properties of compounds containing carbon-sulfur multiple bonds
stabilized by fluorine. Lagow, Bierschenk, Juhlke, and Kawa
(Ch. 5) report on direct fluorination methods for the synthesis of perfluoropolyethers and on possible areas of application for these compounds. Adcock (Ch. 6) describes aerosol
direct fluorination, claimed to be a universal method for
perfluorinations. Rozen (Ch. 7) describes electrophilic fluorinations of organic compounds using fluorine or other fluorinating agents. Olah and Li (Ch. 8) demonstrate that oniumpolyhydrogenfluorides have a wide range of applications as
fluorinating agents. Burton (Ch.9) describes the use of
AnRru.. CIicm. 1111. Ed. Engl. 1993. 32, No. 7
organometallic compounds containing perfluoroalkyl groups
for the synthesis of organofluoro compounds. Prakash
(Ch. 10) reports on nucleophilic perfluoroalkylations using
perfluorotrialkylsilanes. Farnham (Ch. 11) describes the use
of organosilicon reagents in synthetic organofluorine chemistry. Shteingarts (Ch. 12) discusses electrophilic ips0 reactions of polyfluoroarenes from the standpoint of synthetic
applications. Takenaka and Lemal (Ch. 13) discuss the perfluorobenzeneoxide-perfluorooxepin system. Krespan and
Dixon (Ch. 14) describe the chemistry of perhalogenated
dioxans and dioxens. Welch, Yamakazi, and Gimi (Ch. 15)
report on the Claisen rearrangement of fluoroacetamide aceta1 as a method for asymmetric syntheses of compounds of
biological interest. Chambers (Ch. 16) describes the preparation of some unusual fluorinated alkenes and dienes by reactions involving fluoride ions. Lastly Baum (Ch. 17) describes
syntheses of fluorinated monomers for condensation polymerization.
The book covers quite a broad range of topics and gives
a very good overview of the present state of experimental
fluorine chemistry. It includes about a thousand references
which afford a convenient way into the relevant literature.
There is a nine-page subject index which greatly facilitates
using the book as a reference source. The fact that i t originates from a symposium is readily apparent from the widely
differing styles of the chapters, some giving detailed treatments of only a few compounds while others treat many in
a brief manner. However, this variety makes the book agreeable to read for someone who, like this reviewer, works
through it from start to finish-for example, the reader who
is just beginning work in fluorine chemistry.
Stephan Riidiger
Projektgruppe Fluorchemie
Berlin (FRG)
Adsorption of Molecules at Metal Electrodes. (Series: Frontiers of Electrochemistry.) Edited by J. Lipkowski and
P. N. Ross. VCH Publishers, New York/VCH Verlagsgesellschaft, Weinheim, 1992. XI, 414 pp., hardcover
DM 246.00, $ 145.00.--ISBN 0-89 573-786-8, 0-89 573789-2 (set)/3-527-28008-1, 3-527-28007-3 (set)
An electrochemical double layer is formed at almost every
type of phase boundary. The driving forces causing this are
differences in the chemical potentials of the charge carriers
that are common to both phases, even though they may be
present in very different concentrations. The resulting electrical potential difference cannot be measured directly. Adsorbed molecules have a secondary effect on the electrochemical double layer. Where dipolar molecules are involved
there is not only a chemical interaction with the surface but
also a strong electrostatic field effect.
The volume reviewed here contains eight articles dealing
with the adsorption of molecules at metal electrodes. However, the topics covered are much more specialized than the
title leads one to expect. Of the metals considered, mercury
and platinum are by far the predominant ones. Where the
use of surface enhanced Raman spectroscopy (SERS) is described, silver and gold also feature, since these metals are
specific for the technique. The two most important utility
metals, iron and aluminum, are discussed only very briefly in
the article by Plieth et al. The other phase is an electrolyte
solution which contains not only the organic molecules but
also ions such as HSO, or CN- that can be adsorbed. The
methods used to study adsorption include the classical tech-
:(> VCH Vr.riaRsReseifs~hafi
mhH. 0-69451 Weinheim. 1993
057O-oR33j93jo7o7-1107$ 10 OOf ,2510
1 107
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