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Book Review Fine Chemicals for the Electronics Industry. By P. Bamfield

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very expensive, handbook on organoselenium and organotellurium chemistry. It is to be welcomed, since this subject
has not been covered in “Comprehensive Organometallic
Chemistry”. It is an advantage to have selenium and tellurium chemistry treated together, with frequent comparisons of structure and reactivity in the S-Se-Te
series.
This helps the reader to understand the basic trends and
relationships in Main Group VI, and contributes to the
systematization of our knowledge.
Liotta’s “Organoselenium Chemistry”, which is likewise
published by Wiley, consists of nine review articles, dealing with the electrophilic, nucleophilic and free radical
reactions of organoselenium compounds, their oxidation
reactions, and the chemistry of selenium-containing carbanions and organic conductors. These specialized aspects
of selenium chemistry are very well described (e.g. in the
article by H. J . Reich on selenoacetals, carbanions and sigmatropic rearrangements). However, the book as a whole
is by no means an alternative to Volume I of the Patai series, especially as the excellent contributions by 7’.G . Back
o n electrophilic and free radical reactions, and by F. S.
Guziec on selenocarbonyls, in the book edited by Liotta,
are to be followed by articles from the same authors in
Vo I u m e 2 of Pa tai/Rappoport[*].
Wov- Walrher du Mont [NB 857 IE]
Fachbereich Chemie
der Universitat Oldenburg (FRG)
In most of the book the chemistry is easy to follow. In
some chapters, however, the material is not as logically organized as it could be, and this leads to a somewhat disjointed presentation. I n some places the equations are not
adequately explained and consequently are not readily understood. In many cases, results from the literature are
given without comment or a critical evaluation of the results; occasionally the equation for an unusual reaction is
presented without comment or speculation as to the mechanism. To include this kind of commentary, however, is a
formidable task, so it is understandable that the authors
chose not to d o so. In other chapters, the chemistry becomes repetitive such that it possibly would have been better to include tables rather than going through example
after example, each with an equation and verbal explanation.
There are relatively few mistakes and inconsistencies,
most of which will be apparent to organic chemists.
Overall, I highly recommend this book both for those
involved in organotin chemistry and in general organic
chemistry. It not only serves as an excellent text for introducing organotin chemistry, but also is an excellent reference source. It is the only book of its kind available.
John K . Stifle [NB 856 IE]
Department of Chemistry
Colorado State University
Fort Collins, C O 80523 (USA)
Tin in Organic Synthesis. By M. Pereyre, J.-P. Quintard.
and A . Rahm. Butterworths, London 1986. 342 pp.,
bound, =f50.00.--ISBN 0-408-01435-0
This book, containing 17 chapters, is divided into four
parts: Part I is an introduction, containing two chapters.
Part I1 concerns the reduction of various functional groups
with tin hydrides, each of five chapters treating a different
functional group. Part 111 covers the synthetic applications, including chapters on the cleavage of tin-carbon
bonds by various reagents, transmetallation reactions
(primarily for the synthesis of organolithium reagents)
and the coupling reactions of organotin reagents in the
formation of carbon-carbon bonds. Part IV covers syntheses involving tin-heteroatom bonds in seven chapters. The references are collected at the end of each
part (rather than at the end of each chapter). There is
an excellent compilation of references on organotin
chemistry. Unfortunately the references cover only
through 1984 (with a few 1985 references) so there is
a two year gap between writing and publication at a
time when the field was undergoing an explosive development. A few noteworthy books and references on the synthesis of tin compounds have not been listed in the references for Part I. With these exceptions, the references are
quite inclusive.
All areas of tin reagents in organic synthesis have good
coverage, with the possible exception of the synthesis of
certain organostannanes in Part I. For example, the reaction of tin amides with monosubstituted acetylenes to yield
tin acetylides and the mild, palladium catalyzed reaction
of hexaalkylditins with vinyl and aryl halides to yield vinyl- and arylstannanes are omitted. Perhaps too much coverage was given to desulfurization reactions of xanthates
with tin hydrides an: on the benzylation, acylation and alkylation of sugars. The discussion of radical cyclization
reactions in Chapter 3 could have been made more coherent and presented more clearly by utilizing the framework
of Baldwin’s rules.
Fine Chemicals for the Electronics industry. By P. Bumfield.
The Royal Society of Chemistry, London 1986. v, 247
pp., bound, L 27.50.- ISBN 0-85 186-636-0
This book contains 14 papers presented at a specialist
symposium in April 1986, and provides a good insight into
the manufacture of chemicals for high-technology applications. Although each of the papers relates to a specialist
topic, the combined effect provides an excellent and nearly
up-to-date picture of this fascinating branch of materials
science. In addition to the more conventional materials
such as luminescent substances, the topics covered include
newer ones such as optical fibers, ceramics and semiconductors, including materials used in solar energy conversion. It is pleasing that the materials discussed include not
only inorganic, but also organometallic and organic substances. The interaction between manufacturing technology and the requirements to be met for different applications (including those concerning purity) comes out very
clearly. It would have been helpful to have a little more
information under the topic “Sampling and Analysis”, including the techniques and their limitations, e.g. limits of
detection. The chemistry involved in the applications is explained more effectively than the chemical manufacturing
processes, owing to the more informative diagrams provided in the former case.
Nearly every contribution illustrates the complexity of
the materials problems nowadays encountered in the area
of advanced technology. I n almost every case one is concerned with high value products which are used only in
relatively small quantities. Some discussion of the international competitive situation, and of the availability of raw
materials, would have been useful, but would have gone
beyond the scope of the report.
A clear impression emerges that much of this high-technology business still relies to a very large extent on providing tailormade systems designed on an empirical basis for
specific applications. Many such areas are still at a development stage, and one cannot yet predict the final out-
Angew Chem Int Ed Engl 2711988) No. 3
445
come. How quickly the state of knowledge can change in
these areas is strikingly illustrated by the topic “Superconducting Materials”, where already now, only a year and a
half after the symposium, a new era has begun. It is also
clearly evident that here, more than in most other areas of
knowledge, there is a close interaction between materials
science research, development and production, which calls
for much interdisciplinary work. Just as the papers from
this symposium deal with levels of purity which were inconceivable 20 years ago, so one might envisage that the
next 20 years will see the development of a materials scene
altered beyond recognition from that of today.
UIrich Wiese [NB 870 IE]
Wacker-Chemitronic GmbH,
Burghausen (FRG)
Organosilicon Chemistry. By S. Puwlenko. W. d e Gruyter,
Berlin 1986. xi, 186 pp., bound, DM 180.00.--ISBN 311-010329-X
According to the preface the aim of this monograph is to
give an account of the organic chemistry of silicon for industrial and academic chemists. A brief glance through the
list of contents reveals straight away that the book is not
much concerned with the uses of organosilicon compounds for organic synthesis, as one might have assumed
from its title. Instead there is a strong emphasis on systems
containing a silicon-heteroatom bond, with the remaining
silicon valences being usually occupied by alkyl o r aryl
groups, which, of course, can therefore be regarded as organic compounds. Nevertheless, the majority of the reactions described belong more to inorganic than to organic
chemistry, even though organic chemists will find them of
interest and may occasionally use them.
The first short chapter (12 pages) introduces the reader
to the bonding properties of silicon. However, the discussion of the Si-C bond does not include the simple but useful rules as formulated by Herning, which make it easier to
understand the chemistry of organosilicon compounds.
The industrial production of the basic chemicals concerned is touched upon only briefly, in Chapter 2. The
main part of the book (Chapter 3, approx. 90 pages) deals
with the preparation and properties of more specialized organosilicon compounds. A considerable amount of infor-
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mation is collected here on compounds of silicon with
nearly all the other elements of the Periodic Table. It is, of
course, very useful to have a review of the most important
results in this field, but it is questionable whether boiling
points (with pressures given both in Pa and in mm Hg),
melting points, and in some cases details of the preparative
procedure, should also be included in a comparatively slim
book such as this.
Chapter 4 is devoted to the uses of organosilicon compounds in industry, organic synthesis, and medicine. The
synthetic uses of silicon-containing precursors are dealt
with in about 15 pages, with in addition a few of the most
important reactions being described in the previous chapter. This compression of the topic made it especially important to choose representative examples carefully, so as
to illustrate the principles, but such a choice has regrettably not been achieved. The activation (and deblocking) of
organosilicon compounds by flouride ions receives practically no attention. The particular affinity of silicon towards fluorine is not mentioned, and in equation 4.29 the
essential tetrabutylammonium fluoride is omitted. Again,
the discussion of Lewis acid induced reactions fails to
point out the general principles involved. The author classifies silyl enol ethers as protected carbonyl compounds,
despite the importance of their activation for selective
reactions with electrophilic reagents, which is in fact described in some of the examples. It is astonishing that none
of Mukaiyama’s work is cited, and that other pioneers in
this field (Reetz, Fleming, Magnus, Paquette .. .) are ignored or barely mentioned. The index entry Peterson olefination does not appear at all.
The final chapter on analytical methods is again very informative, but on the whole the impression remains that it
is scarcely possible in about 150 pages to effectively cover
such a large field as organosilicon chemistry has now become. Anyone whose main need is for information on applications to organic synthesis will not get his money’s
worth from this book. For that purpose there are better
and less expensive alternatives (the price of about DM 1.per page is at a level seldom reached by other publishers).
Hans-Ulrich ReiJ3ig [NB 837 IE]
Institut fur Organische Chemie und Biochemie
der Technischen Hochschule Darmstadt (FRG)
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446
Angew. Chem. Inr. Ed. Engl. 27 (1988) No. 3
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