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Book Review Houben-Weyl. Methods of Organic Chemistry. Additional and supplementary volumes to the 4th Edition. Vol. E12 b. Organotellurium Compounds. Edited by D. Klamann

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are not put off by its high price, which is not justifiable for
a “textbook”, despite the high standard of production and
the clear and carefully prepared contents.
Giinther Tolg
Institut fur Spektrochemie und angewandte Spektroskopie
Dortmund (FRG)
Houben-Weyl. Methods of Organic Chemistry. Additional
and supplementary volumes to the 4th Edition. Vol. E 12 h.
Organotellurium Compounds. Edited by D. Klamann.
Thieme, Stuttgart, 1990, xli, 1004 pp., hardcover
DM 1340.00-ISBN3-13-219904-4.
The series “Methoden der Organischen Chemie” was established in 1909 by Theodor Weyl and continued in 1913 by
Heinrich Houben. At that time, publishing a handbook in
organic chemistry in German seemed most appropriate. Today, more than eighty years later, changing the “official”
language of Houben-Weyl from German to English seems
just as well motivated. I am sure the change will increase the
international character of the series even more and I would
like to congratulate the editors on their decision.
Organotellurium compounds were previously described
by Houben-Weyl in 1955 (Vol IX), together with organosulfur and organoselenium compounds. At that time Rheinboldt used 292 pages for the description of the surprisingly
old but little explored fields of organoselenium and organotellurium chemistry. A few years ago, organosulfur chemistry was updated in two volumes of Houben-Weyl, while
the work with the organoselenium volume(s) is presently
ongoing.
The last twenty-five years have seen a steady increase in
the number of publications in the field of organotellurium
chemistry. Recently, a number of useful organic transformations brought about by organotellurium reactions and
reagents has focused the attention of synthetic organic
chemists on the area. Thus, organotellurium chemistry,
viewed by many as rather odd and peculiar, has now developed into an almost respectable field of research close to the
mainstream of organic chemistry.
The author, Kurt Irgolic, was very well prepared for the
gigantic work of putting together a volume of Houben-Weyl.
In 1972 he summarized all previous work in the field in “The
Organic Chemistry of Tellurium” which has since been frequently used as reference by all involved in organotellurium
research. For many years thereafter he also published annual
reports on the chemistry of organic tellurium compounds in
the Journal of Organometallic Chemistry. Unfortunately, this
work was disrupted in 1980. Since that time organotellurium
chemistry has been treated in depth only in the Patai series,
“The Chemistry of Organic Selenium and Tellurium Compounds”, Vol. 1 1986; Vol. 2 1987. Due to the organization
of the Patai series, which focuses attention on a number of
diverse aspects of the field, these volumes are complementary to, rather than overlapping with, the Houben-Weyl volume.
The contents of the present volume are logically organized
in a way similar to the one used by the author in his previous
writing. Thus, the organic tellurium compounds are classified according to the number (1 -6) of carbon-tellurium
bonds in the molecule, and their reactions subdivided according to the traditional Houben-Weyl scheme of presentation (i.e.. A. Preparation; B. Transformations). Polymeric
tellurium compounds as well as heterocyclic (3 -7-memAngen. C h m . Int. Ed. Engl. 31 11992) N o . 2
0
bered) organic tellurium compounds are treated in separate
sections. In addition, a chapter (150 pages) is devoted to
organic tellurium compounds without a carbon-tellurium
bond in the molecule. Compounds described in this section
include molecules where the organic moiety is separated
from tellurium by another heteroatom such as oxygen, sulfur, selenium, silicon, or phosphorus. These compounds
were traditionally not classified as organotellurium compounds but left in a no-man’s-land between inorganic and
organic chemistry.
The classification of chemical reactions as “Preparations”
or “Transformations” in the treatment of various classes of
compounds is not always consistent. For example, the reaction of a diorganyltellurium(u) species with a halogen, to
give the corresponding diorganyltellurium(iv) dihalide is
sometimes treated as a method of preparation, sometimes as
a transformation of the class of diorganyltellurium(II) compounds. The latter treatment is the preferred one. The formation of complexes of organotellurium compounds with
transition metals or electron-deficient organic molecules is
usually found under “Preparations”. However, in some
cases these compounds are also treated under “Transformations”. In my opinion the latter classification is more logical
and should be used consistently.
A third category of classification is introduced for
diorganotellurium dihalides on p. 577: “C. Diorganotellurium dihalides as synthetic intermediates”. However, when the
similar use of diorganotellurium compounds is discussed
earlier on p. 480, the material is presented as a transformation.
The present supplementary volume of Houben-Weyl contains a respectable number of references and examples from
the period (1840-1955) covered by volume 1X. The old results are often presented in the light of new findings and
contribute to a feeling of complete understanding and coverage of a certain class of compounds or reactions. In other
cases the old material was too sparsely treated in the previous version and was in need of an expansion.
The overall impression of the present volume of HoubenWeyl is that of a complete coverage of the field. The number
of papers not included can probably be counted on your
fingers. This completeness will of course make the book invaluable for all involved in organotellurium research and
those in other areas in need of information concerning
organotellurium chemistry. However, the philosophy on
which Houben-Weyl was established requires not only a
complete description of preparative methods but also their
critical evaluation. While going through the representative
examples of the present volume, I sometimes got the impression that the author should have been more selective/critical
in his choice. There are too many full-detail preparations
where the yields do not exceed 10%. For example, nobody
“skilled in the art” would ever consider trying to execute the
1 % yield synthesis of diphenyl ditelluride described on
p. 270, when there are so many better methods available.
Similarly, on p. 2 the existence of tellurium(I1) dihalides is
discussed, and it is concluded that they probably do not exist
as molecular entities in the solid state. Nevertheless, on p. 37
an example is presented where TeC1, is used as one of the
reactants for the preparation of a ferrocene derivative. Likewise, on p. 841 TeI, appears in an example describing the
synthesis of a heterocyclic tellurium compound.
An index of authors and a compound index is included at
the end of the book. The compound index is very good if you
are looking for a particular compound; however, it is of little
help if you are searching for something else. I think a book
of this size could afford also a subject index.
VCH Verlagsgesellschafr mbH, W-6940 Weinheim, 1992
OS70-0833/92/0202-0237$3.50+.25/0
237
The number of printing errors is kept to a minimum
throughout this volume of Houben-Weyl. Less than 50 errors (and only very few serious ones) were noted while going
through the material. Except for p. XXXVII (where a terrible 20 % of the references contain minor errors or are incomplete) the citation is comparable in quality with that found in
the best journals.
In conclusion, the updated Houben-Weyl volume on
organotellurium compounds is a masterpiece which will be
enthusiastically received by all readers with an interest in
tellurium chemistry.
Lars Engman
Department of Organic Chemistry
Royal Institute of Technology
Stockholm (Sweden)
ElectrochemicalInterfaces. Modern Techniques for in-situ Interface Characterization. Edited by H . D . Abruna. VCH
Publishers, New York/VCH Verlagsgesellschaft, Weinheim, 1991. xviii, 589 pp., hardcover DM 182.00.ISBN 0-89573-715-913-527-27840-0
In seeking to describe and understand electrochemical
processes that occur in the solid/liquid transition region,
experimental data obtained by in-situ measurements are especially valuable. A classic example where this applies is the
technique of cyclovoltammetry (CV). In this the flow of
charge is recorded as a function of the potential, but the
method is intrinsically incapable of yielding information of
a highly specific kind. For this reason other techniques that
can be used in combination with CV have recently been
developed to complement it. Particularly interesting results
can be obtained by carrying out in-situ measurements simultaneously with CV studies. This rapidly developing field is
the subject of the specialist book edited by H. D. Abruna
(Cornell University) which is reviewed here.
The book, with nearly 600 pages, contains ten chapters
following an introduction by the editor, and there is a 22page subject index at the end.
The individual chapters deal with X-ray absorption spectroscopy, surface X-ray scattering, X-ray standing waves,
measurements of surface forces, surface-enhanced Raman
scattering, nonlinear optical methods, surface infrared spectroscopy, in-situ Mossbauer spectroscopy, radioactive labeling, and measurements with vibrating quartz crystals. The
contributions have been printed by the camera-ready
method, and all except one are written by American authors.
Apart from the fact that several of the figures in Chapter 1
have been interchanged (see the comments of the editorial
office), the contributions are impressively well prepared :
they are logically set out, illustrated by clear figures, and
packed with information. In each chapter the main emphasis
is firmly on the description of the experimental techniques,
but this is supported by informative examples of applications. In the description of the standing wave X-ray technique for characterizing the phase boundary region, it would
have been desirable to have examples of a wider range of
applications. Unfortunately the chapter on in-situ measurements with vibrating quartz crystals includes only two examples of applications, namely to coverages deposited in the
under-potential range, and (in more detail) to studies of mass
transport during redox processes in polymer films.
The selection of topics covered by the chapters is not exhaustive, nor can one expect it to be. However, it is notice238
0 VCH Verlagsgeselischafi mbH. W-6940 Weinheim, 1992
able that some important methods are not mentioned, for
example UVjVIS reflectance spectroscopy, ellipsometry and
photocurrent spectroscopy. It is also regrettable that in-situ
topographic methods such as scanning tunneling microscopy (STM) and atomic force microscopy (AFM),
which give a microscopic image of the surface, in some cases
with atomic resolution, are not included. Furthermore, there
seems to be no logical connection between the individual
chapters. The fact that articles on optically based techniques
alternate with others on non-optical methods prevents a systematic presentation of the subject matter. Consequently it is
hardly surprising that the book lacks a final summary linking the various methods and results and evaluating them.
The book has a binding of appropriately high quality.
Considered as a whole it provides a good insight into the
progress that has been made in the development of various
in-situ techniques. However, one cannot overlook the shortcomings in the choice of topics and their relative emphasis,
and the lack of a logical arrangement of subject matter, with
the result that the reader fails to get a deeper understanding
of the progress made. The book is unquestionably of considerable importance to scientists with interests in interfacial
electrochemistry, and it should therefore be in every relevant
library, especially since the price of DM 182.00 will prevent
students from buying it.
Rolf Schumacher
Schering AG, Forschungsabteilung GT
Berlin (FRG)
Chemistry of Organosulfur Compounds. General Problems.
(Ellis Horwood Series in Organic Chemistry). Edited by
L. I. Belen’kii. Ellis Horwood, New York, 1990. 378 pp.,
hardcover $ 129.95.-ISBN 0-13-132051-3
Organosulfur chemistry traditionally occupies a position
of considerable importance in Soviet research, and there is
even a special scientific committee to promote it. The monograph reviewed here is based on a status report on work in
this field that was prepared in 1986 by various authors,
mainly from Moscow and Irkutsk. For this English version
the Russian text has been rearranged and updated (but, as
becomes apparent, only in parts). The 15 chapters of this
version deal with the preparation of organosulfur compounds, their transformations, and the methods used to
study them. Details of the chapters are as follows: Modern
Principles of the Synthesis of Organosulfur Compounds
(M. G. Voronkov et al., 14 pp., 25 references); Radical Reactions of Some Thiocarbonyl Derivatives in Solutions
(R. Kh. Freidlina et al., 21 pp., 64 references); Thermal Reactions and High Temperature Syntheses of Organosulfur
Compounds (M. G. Voronkov et al., 20 pp., 56 references);
Photochemical Synthesis and Transformations of Organosulfur Compounds (N. N. Vlasova, 22 pp., 65 references);
Radiochemical Synthesis and Transformations of Organosulfur Compounds (E. M. Nanobashvili, 8 pp., 11 references); Sulfur-stabilized Carbanions and their Synthetic Use
(F. M. Stoyanovich, 43 pp., 267 references); Formation of
C-C Bonds Using Sulfur-containing Electrophilic Reagents
(W A. Smit et al., 32 pp., 99 references); Catalytic Synthesis
of Organosulfur Compounds (A. V. Mashkina, 20 pp., 40
references); Methods of Desulfurization and their Use in
Organic Synthesis (L. I. Belen’kii, 36 pp., 189 references);
Investigation of Organic Reactions by the Use of Radioactive Sulfur (V. M. Fedeseev, 15 pp., 49 references); Mass
0570-0833/92j0202-0238$3.50+ .2510
Angew. Chem. Int. Ed. Engl. 31 (1992) No. 2
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