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Book Review Heteroatom Chemistry. Edited by E. Block

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BOOK R E V I E W S
Profiles, Pathways and Dreams. Autobiographies of Eminent
Chemists. Edited by 1 I. Seeman. American Chemical Society, Washington, D. C. 1990. D. J. Cram. From Design to
Discovery. xxi, 146 pp., hardcover $24.85.--ISBN0-84121768-8; C. Djerassi. Steroids Made it Possible. xxiv,
205 pp., hardcover $24.85.-ISBN 0-8412-1773-4; E. L.
Eliel. From Cologne to Chapel Hill. xxxi, 138 pp., hardcover $24.95.--ISBN 0-8432-1767-X; J. D. Roberts. The
Right Place at the Right Time. xix, 299pp., hardcover
$24.95.--ISBN 0-8412-1766-1
Jeffrey I. Seeman, an American industrial chemist who
tells us that he has always been interested in the human side
of scientific developments, suggested to the books department of the American Chemical Society (ACS) in 1986 that
they should publish a volume of autobiographical essays by
eminent chemists. The ACS took up this idea, but both they
and the editor soon found that the project began to develop
a life of its own, so that by the time it is finished (at least for
the time being!) there will be no less than 22 individual volumes. The series has now been given the general title “Profiles, Pathways and Dreams”, and the first four autobiographies (consisting of nearly 800 pages altogether!) have appeared and are reviewed here. My verdict can be summarized
in one sentence: please let us have more soon! (Since this was
written the number of volumes has in fact grown to ten).
The clever and carefully-considered choice of authors
means that the level of interest in the series is unlikely to fade
soon. As well as applying the criterion that each author must
have made fundamental contributions to organic chemistry
over a long period, much importance has also been placed on
maintaining the international quality of the project. The authors eventually enlisted (ominously, it is stated in the preface that “Not all who were invited chose to participate, and
not all who should have been invited could be asked”) represent experiences of teaching and research in thirteen countries altogether.
These first volumes of the series can be read at several
quite different levels, and this is likely to be true also of later
volumes. In the first place, of course, they are the life stories
of the authors, in which the human dimension and the
dreams come out to a varying degree depending on temperament and frankness, sometimes strongly (Djerassi) and
sometimes with more reserve (Cram). Here each reader will
develop his or her own particular affinities. For me it was
Roberts’ autobiography that pleased most: his sober style
and absence of illusions, his modesty (“Memory of the titans
of any given era of modern chemistry tends to fade rapidly
from generation to generation”), the humor, both overt and
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veiled, and the occasional adverse comments about colleagues.
Secondly, these “blue volumes” (each with a profile on the
cover in gold of the author portrayed therein!) are also excellent textbooks of chemistry, since their authors describe in
detail how their research aims have developed over the
decades: by studying the classic examples one gains mastery
of a science. In this connection it is also interesting to note at
how early a stage each author discovered his (scientific) leitmotif in every case, and how steadfastly he continued to
pursue it over a very long period and developed it further
using the latest techniques. This possibly characterizes one of
the main differences compared with present-day research in
organic chemistry: the research of the fifties to seventies
which is described in these autobiographies (the average age
of the authors being around seventy) was more noticeably
“inner-directed” (to use a term coined by David Riesmnn, a
sociologist of that period), in contrast to the strongly “outerdirected” research of today. The main reason for this could
be the considerable changes that have occurred in the system
of supporting and rewarding research. The scarcity of financial support and of material resources in general in those
earlier years forced researchers to be more self-reliant. Here
again Roberts provides a good example, constructing his
own glass apparatus, and later his own NMR spectrometers
which he continued to develop. In those days there was no
talk of creativity prizes, reagents of the year, or other such
gimmicks originating from the world of scientific marketing.
Thirdly, these volumes are a tribute to the American university system. This is at the same time both very elitist and
democratic in character, has a strong internationalist tradition, as is clearly shown by the experiences of the immigrants
Djerassi and Eliel during their first years in American universities, and provides academic freedom (researchers remain
almost exclusively researchers, rather than administrators as
tends to happen in Germany).
This series of volumes will not add up to a history of
modern organic chemistry; that purpose cannot be achieved
through autobiographies, and it will certainly not be attempted. On the other hand, when the series is complete we
shall have a very rich and colorful patchwork of chemistry,
made up additionally of many interesting and sometimes
amusing snapshots, together with many brilliant highlights.
Henning Hops [NB 1159 I E ]
Institut fur Organische Chemie
der Technischen Universitat Braunschweig (FRG)
Heteroatom Chemistry. Edited by E. Block. VCH Publishers,
New York 1990. xii, 376pp., hardcover DM178.00.ISBN 0-89573-743-4
“Heteroatom chemistry” is usually understood to mean
the organoelement chemistry of the elements in main-groups
3 to 7 of the Periodic Table (i.e. the 13th to 17th groups). This
book is based on twenty plenary lectures delivered at the
International Conference on Heteroatom Chemistry
(ICHAC) held in Albany, NY, in 1989. The presentation of
this material in book form is almost beyond reproach.
This very extensive subject could not be covered in a mere
376 pages; the editor has therefore limited the contents to an
overview of the current situation regarding the applications
of heteroatom compounds (excluding those of nitrogen and
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Angew. Chem. Inr. Ed. Engl. 30 (1991) No. 9
oxygen), mainly in synthetic organic chemistry. In addition
a few articles are devoted to unusual types of bonding in
compounds of main-group elements. The choice of eminent
authors has ensured that the book is successful in meeting
these aims.
K Apeloig deals with bonding and structure in some unusual silicon compounds. This article is a good summary of
the same author’s contribution to “The Chemistry of Organic Silicon Compounds” (edited by S. Putui and Z . Ruppoport), which appeared in 1989. A . J Arduengo IZI and D . A .
Dixon present experimental and theoretical evidence showing that trivalently bonded compounds of the “pnictogen”
elements can undergo not only the familiar textbook vertex
inversion process (tetrahedron-trigonal-planar intermediate-tetrahedron), but also an “edge inversion process” (tetrahedron-square-planar intermediate-tetrahedron). This
new process is illustrated by the example of Arduengo’s Tshaped compounds of main-group elements. In discussing
the problem of color in pentaarylbismuth compounds K.
Seppeft draws attention to the unusual bismuth-carbon
bonding in these hypervalent species; relativistic effects must
be invoked to account for the phenomena that are observed.
This group of contributions dealing mainly with theoretical
and physical chemical aspects ends with an article by J B.
Lurnhert, G. Wung and E. C . Chelius in which they discuss the
j3-effect of trimethylsilyl, -germyl and -stannyl groups in the
solvolysis of cyclohexyl and cyclopentyl derivatives.
Four articles are devoted to the reactivity and synthetic
applications of sulfoxides. Those by H . B . Kugun and A .
Ohno are concerned with chiral sulfoxides, whereas 0. De
Lucchi et al. discuss atropisomeric binaphthylsulfones and
-sulfoxides as chiral auxiliaries. N . Furukuwu describes an
investigation into the question of whether sulfuranes are
formed as intermediates in the reaction of sulfoxides with
organometallic reagents, and considers the possible synthetic
applications of these experiments.
A further contribution on the chemistry of hypervalent
heteroatoms is provided by D . H . R. Burton, who describes
ligand coupling reactions applied to pentacoordinated bismuth compounds. r - Z . Huung et al. give an impressive account of the use of arsene ylides in synthesizing polyenes and
sensitive natural products. Some insights into the chemistry
of organoselenium compounds are provided by K Ando and
N . Tokitoh, who describe the photolysis and pyrolysis of
selenium- and sulfur-containing heterocycles to form highly
reactive intermediates. The section on polyselenium and
polysulfur heterocycles is especially interesting, and includes
some hitherto unpublished results. is G. Buck et al. report on
the selenosulfonation of alkenes and alkynes and some applications of this method in steroid chemistry. A . Krief et al.
have succeeded in synthesizing molecules in which quaternary carbon atoms are linked together, by proceeding via
a-lithioselenides.
Two articles deal with the chemistry of low-valency compounds of main-group elements. In the first of these M .
Regitz discusses the synthesis of phosphaalkynes and the
chemistry based on these. Although detailed and up-to-date
reviews of this topic already exist,[*]the fascinating possibilities opened up by this chemistry simply had to be included
in this book. The second article is an updated survey of the
chemistry of siloxy-substituted silenes, an area which is the
specialty of A . G . Brook. 7: Cohen describes the use of
phenylthioethers to synthesize carbanions which would otherwise be accessible only with great difficulty or not at all.
[*] M. Regitz. P. Binger, Angew. Chem. 100(1988);Angew. Chem. Inl. Ed. Engl.
27 (1988), M. Regitz, Chem. Rev. 90 (1990).
Angen. Chem Int. Ed. Engl. 30 (1991) No. 9
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The sections on the preparation of dianions from epoxides
and dioxetanes are particularly interesting. These anions are
very useful building blocks, for example in synthesizing
spiroketals.
Some results obtained in the very promising field of
polydentate Lewis acids, which in contrast to that of
polydentate Lewis bases is still only in its infancy, are described with the help of examples by H . G . Kuivulu. Some
new sterically strained boron compounds are described by
M . Luppert et al. Nearly all these results are previously unpublished; however, the coverage is rather too brief for my
taste (9 pages), especially as this is the only article dealing
with boron chemistry. H . Sukurui gives a brief account of
some interesting metal-induced cyclooligomerizations of
silylated cyclic polyalkynes, and of the synthesis and structure of hexakis(trimethylsily1)benzene. The book ends with
an article by K. Tang on copper and silver complexes with
sulfur ligands, which is certainly worth reading, although it
does not really fit into the subject of the book.
The literature citations in all the articles are, without exception, fairly recent or very recent; references to reviews are
also included. The choice of topics and their treatment give
no cause for criticism. As the book is essentially a conference
proceedings report, it provides insights into the current state
of research in selected areas rather than comprehensive reviews. In so doing it succeeds, briefly but succinctly, in conveying an appreciation of the principles underlying the reactivity of each element or molecule discussed. In general it is
exactly the personal points of view expressed in the treatment of the topics that give the book its appeal, and the
authors’ love of their special fields of research is evident
between the lines. The fact that the dominant heteroatom
elements are sulfur and selenium (at least in nine of the
twenty articles), may be a consequence of the editor’s area of
interest. This excellent book can be recommended to anyone
who wants a rapid survey of the currently “hot” topics in
main-group chemistry. However, the price is already approaching the “pain threshold” (and is well above it for
students), which means that for future volumes, if the basic
concept is to be maintained, the possibility of paperback
editions should be considered.
Hunsjorg Grutzmucher [NB 1134IEl
Anorganisch-chemisches Institut
der Universitat Heidelberg (FRG)
Chemistry of Alicyclic Compounds. Structure and Chemical
Transformations. (Series: Studies in Organic Chemistry,
Vol. 38). By G. Huufe and G . Munn. Elsevier, Amsterdam
1989. 468 pp., hardcover DFI 350.00.-ISBN 0-44498878-5
This book lives up to the authors’ claim : it is suitable as a
standard text and guide for the student, and it can be used by
a practising chemist to increase the depth of his knowledge
of alicyclic compounds. Obviously, the chemistry of alicyclic
compounds is so large a subject that it is not possible for the
authors to cover it completely. Their treatment is therefore
concentrated mainly on small to medium-sized ring systems.
The book, which is practically free of errors that affect the
meaning, is divided into six self-contained chapters. The first
chapter, and also the two that follow it, are written in textbook style and should therefore be easily understandable
even by second-year chemistry undergraduates. Chapter 1
deals with the systematic description of the structures of
alicyclic compounds. The topological and topographical as-
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