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Book Review Radicals in Organic Synthesis Formation of CarbonЦCarbon Bonds. By B. Giese

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specific compounds covered in the volume. For those developing a new EIA method, this volume provides a variety of approaches to immunoassay and may be a suitable
starting point for the development of a new assay. Workers
unfamiliar with immunochemistry may find this volume
difficult to read and should see chapter 2.7 of volume I, if
not a general textbook description of the science involved
in order to be familiar with some of the terminology
The appendix to this volume contains lists of symbols,
quantities, units and constants; abbreviations for chemical
and biological compounds; and formulae useful in spectrophotometry. It is not as extensive as in previous volumes.
Anyone regularly using immunoassay methods in their
work should have this book. Those needing to understand
the nature and application of EIA and the practical aspects involved would d o well to read part o r all of volume
Mark A . Findeis, George M . Whitesides [NB 787 IE]
Harvard University, Department of Chemistry
Cambridge, MA 02 138 (USA)
Infegral/Structural Polymer Foams. Technology, Properties
and Applications. Edited by G. Henrici-Olive and S. 01ive. Springer, Berlin 1986. xxii, 295 pp., bound, D M
198.00.- ISBN 3-540- 15038-2
Integral polymer foams, o r structural polymer foams (these
being the names used in Europe and in the USA respectively), have a cellular structure, with the density increasing outwards from the core to a rigid skin, thus imitating
the structure of wood o r bone. Integral polymer foams are
often used as a wood substitute.
F. A . Shutov and many other authors from Germany, the
USA and elsewhere were involved in putting together this
very carefully written book. It deals with the basic relationships between the morphology and properties o n the one
hand, and the formulating, the equipment and its setting
up, and the manufacturing variables on the other. The applications are discussed, together with a summary of the
molding of the materials and marketing problems. An economic analysis of commercial processes for marketable
materials is also included.
The book deals with the starting materials, the technology of integral polymer foams, and applications using polyurethanes, polystyrenes, polyvinyl chloride, polyolefins,
ABS copolymers, polyphenylene oxides, polycarbonates,
polyamides, polyesters, polyacetals, polyimides, epoxides,
phenyl resins, and other starting materials. It ends with a
chapter on rigidity calculations, molding techniques, and
considerations affecting manufacturers and users.
Useful features are the numerous figures illustrating
equipment, the engineering drawings, flow diagrams and
schematic diagrams, together with detailed indexes of
manufacturers, processes, products, abbreviations, a contents list, and an excellent subject index.
The book is suitable both for those concerned with the
production of these materials and for users, and also for
students of the science, technology and applications of polymers.
Frank Wingler [NB 785 IE]
Central Research Laboratory,
Bayer AG, Leverkusen (FRG)
Angew. Chem. Inr. Ed. Engl. 26 (1987) No. 4
Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds. By B. Giese. Pergamon Press, Oxford 1986.
XIII, 294 S., Paperback, $ 25.00.--ISBN 0-08-032494-0
During the last decade organic free-radical chemistry has
undergone a remarkable metamorphosis from a rather prosaic area of limited utility for the construction of carboncarbon bonds, except in polymers, to one of major synthetic importance with methods capable of providing chemo-, regio- and stereo-selectivity far beyond the most optimistic expectations of early workers in the field. Professor Giese, one of those who has played a significant role in
bringing about these developments, now provides a timely
account of the mechanistic basis and synthetic applications of free-radical methods, abundantly illustrated with
examples from the recent literature.
The book opens with a short introduction in which well
earned credit is rightfully accorded to those physical-organic chemists whose studies in this area laid that kinetic
and mechanistic base upon which the present cornucopia
of synthetically useful methods so firmly rests. The main
substance of the book is contained in the following four
long chapters, each of which deals with a major topic and
is subdivided into a number of smaller sections.
In the first of these chapters (Basic Principles) the subsections cover general aspects of syntheses with radicals,
elementary reaction steps between radicals and non-radicals, and the comparison of radicals and ions in synthesis.
The Author wisely advises the reader to study this chapter
carefully since an understanding of the factors which affect the relative reactivities of radicals is essential to the
successful application of radical reactions in synthesis.
This point is nicely exemplified by a thorough examination
of the way in which a knowledge of the rate constants for
the individual steps in the reaction of alkyl halides with
activated olefins in the presence of trialkylstannane allows
the choice of optimum experimental conditions. Another
particularly useful topic in this chapter deals with the frontier-orbital approach to radical addition processes.
The next chapter provides a comprehensive account of
the intermolecular formation of aliphatic carbon-carbon
bonds. It is mainly devoted to addition processes subdivided according to the nature of the reagent (tin hydrides,
mercury hydrides, etc.) which reacts with the adduct, but
there is also a small section covering synthetic applications
of radical-radical reactions. Pleasing features of this and
following chapters are the diversity and number of illustrative examples, drawn for the most part from the very recent literature. Indeed dramatic evidence of the level of
current activity in this area is provided by the fact that 55%
of the 250 or so papers cited in this chapter have been published during the last six years.
The proportion of very recent papers cited is even higher
in the next chapter which deals with intramolecular formation of aliphatic carbon-carbon bonds. The many examples in this chapter of the formation of bi- or tri-cyclic ring
systems, often related to such important natural products
as triquinanes, cephems, and pyrrolizidine alkaloids,
clearly shows why this radical methodology is currently attracting so much interest. By comparison the formation of
bonds to aromatic systems is somewhat neglected. However, chapter 5 which deals with this topic, indicates the potential synthetic utility of SRNlreactions, of additions involving aryl radicals, and of homolytic substitution in both
aromatic and heteroaromatic systems.
The last chapter (Methods of Radical Formation) is
quite different from those that precede it. It does not provide a full discussion of the ways in which radicals can be
generated; rather it is a summary index of all the various
methods referred to in earlier chapters and as such provides a most useful way of rapidly finding illustrative examples of their use.
In summary, this is a splendid book. Inevitably it is
stronger in some areas than in others; I personally would
have welcomed a little more discussion of photochemical
methods, of phenolic coupling, and of intramolecular aryl
addition. But these are minor quibbles. Overall it gives not
only a good account of the power and diversity of presently available methods, but also a feeling for the current
state of intense activity in this area, and for the potential
for new breakthroughs. Anyone who wishes to use the
present methodology o r to participate in the exciting developments that lie just around the corner should read this
book from cover to cover.
A . L. J. Beckwith [NB 823 IE]
Research School of Chemistry
Australian National University, Canberra (Australia)
The Practice of Quantitative Gel Electrophoresis. By A .
Chrarnbach. VCH Verlagsgesellschaft, Weinheim 1985.
xv, 265 pp., bound, DM 110.00.-ISBN 3-527-26039-0
It must be said at the outset that this is an extremely useful
book. Those who have previously used polyacrylamide gel
electrophoresis (PAGE) only as an analytical technique
will have found the texts by Weber and Osborn, by
Laemrnli and by O’Farrell, sufficient for obtaining reproducible one- o r two-dimensional protein patterns, or for
determining “apparent” molecular weights. The present
book treats sodium dodecyl sulfate PAGE (SDS-PAGE) as
just one of the possible forms of gel electrophoresis; everyone who casts gels knows that PAGE did not begin with
Maize1 or Laernrnli, but a glance at current issues of biochemical journals might lead one to think that most other
forms of analytical gel electrophoresis are now being forgotten.
A . Chrarnbach sees gel electrophoresis as an integrated
whole. Consequently, as is stressed in the preface, polyacrylamide gel and agarose gel electrophoresis, isotachophoresis and electrofocussing are treated in unity. The objective is to isolate specific proteins or protein complexes
by an appropriate combination of these various methods
for passing a protein mixture through a gel. In this connection the native macromolecules themselves are chiefly of
interest, as distinct from the dissociated individual pro-
teins that are studied in SDS-PAGE. The concept of
“quantitative” gel electrophoresis results from the methodology now available; suitable conditions for achieving a
separation are determined using computer programs, taking into account results from theoretical physical chemistry and from statistics. (Some programs are listed in the
appendix, while for others a source from which they can
be obtained is given in the text.) Experimental arrangements for quantitative electrophoresis are described in detail. In the author’s opinion no manufacturer yet offers a
system which comes near to meeting all the requirements,
e.g. precise temperature control and efficient heat conduction; hence the advice is to build one’s own. Following a
precise account of the properties of polyacrylamide and
agarose gels, the many different available buffer systems
for running these gels are described. This leads to a detailed plan for determining the “happiness conditions”
which apply to the protein to be isolated, i.e. those conditions under which the protein will retain its native form
during its passage through the system. From the determination of the optimal concentration, degree of cross-linking of the separating gel, and p H value, the computer program is used to define conditions for fractionation by
PAGE, electrofocussing or isotachophoresis.
The book is arranged in a clear way, and is provided
with a carefully compiled index and an extensive appendix. Information on a specific application can be found
without difficulty by using the detailed contents list, and
the many cross-references give rapid and precise access to
important additional information. This book will probably
be too complicated for someone wishing to carry out a gel
electrophoresis for the first time. For all others, though,
who daily encounter problems of protein separation, and
are not regular readers of Electrophoresis, it will certainly
provide useful ideas for new experiments, and open u p the
possibility of using an advanced technique.
Harald Herrmann [NB 783 IE]
Institut fur Biochemie
der Universitat Wien (Austria)
The title of the communication by C. A. McAuliffe, B.
Beagley, G. A. Gott, A. G. Mackie, P. P. MacRory, and R.
G. Pritchard, Angew. Chern. Znt. Ed. Engl. 26 (1987) 264
should read “Structure of Triphenylarsanediiodine,
[Ph3As.12], a Compound Formed in the Thermal Decomposition of [ M ~ ( O A S P ~ ~ ) & S O ~ ) ~ ] . ’ ’
Regrsrered names. rrademarks. erc used in rhislournal. even x ’ h m nor marked as such. are nor 10 be ronsrdered unprorecred b? law.
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Angew. Chem. In!. Ed. Engl. 26 (1987) No. 4
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bond, synthesis, carbonцcarbon, book, organiz, formation, radical, giesl, review
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