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Book Review Houben-Weyl. Methoden der Organischen Chemie. Band E13 Teil 1 und 2 Organische Peroxo-Verbindungen. 4th Edition. Edited by H

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There is a great deal in this book that the attentive reader and
student may learn, also by reading between lines. Organic
chemistry without synthesis is hard to imagine. Conversely
and even more cogently, organic synthesis remains the essence of organic chemistry.
H. Martin R. Hoffmann [NB 1002 IE]
Institut fur Organische Chemie
der Universitat Hannover (FRG)
[ l ] D. L. Boger. S. M. Weinreb, Hetero Did-Alder Methodology in Organic
Synthesis, Academic Press 1987.
[2] D. Bellus, B. Emst. Angew. Chem. f00 (1988) 820; Angew. Chem. I n l . Ed.
Engl. 27 (1988) 797.
131 B. B. Snider, Chem. Rev. 88 (1988) 793.
141 R. S. Liu et al., Can. J. Chem. 66 (1988) 528.
[S] Chapter 2 of this volume. refs. [88a-d].
[6] R. Scheffold, Chimiu 43 (1989) 37-38.
Metalloproteins, Chemical Properties and Biological Effects.
(Series: Bioactive Molecules, Vol. 8). Edited by C. I .
Otsuka and 7: Yamanaka. Elsevier, Amsterdam 1988. xiv,
572 pp., hardcover, HFI 450.00. - ISBN 0-444-98887-4
This book is the result of the combined efforts of 54 authors. As one expects from the title, it contains chapters on
metalloproteins and metalloenzymes containing one or more
of the metals magnesium, calcium, vanadium, manganese,
iron, cobalt, nickel, copper, zinc, molybdenum, tungsten and
selenium; in addition there are chapters on flavines and metal ions, complexes formed by nucleosides and nucleotides
with metal ions, carcinogenicity of metal ion, and antitumor
activity of metal compounds. Finally, there is a chapter on
affinity fractionation using metal chelates.
The book is mainly suitable as a work of reference, since
much of the information which it contains is presented in the
form of useful tables. However, this only applies to the older
literature; results from the last four years receive little coverage or are treated only superficially, sometimes only by a
“note added in proof”. The individual chapters are very
varied in quality. For example, the sections on molybdoenzymes and nickel enzymes are hardly up to the standard of
a good textbook treatment. Nowwhere is there a critical discussion of the historical significance of particular topics, e.g.
of the discovery of nickel in urease. These failings detract
appreciably from the value of this otherwise interesting
Rudolf Kurth Thauer [NB 1003 IE]
Fachbereich Biologie
der Universitat Marburg (FRG)
Houben-Weyl. Methoden der Organischen Chemie. Band
E13, Teil 1 und 2: Organische Peroxo-Verbindungen. 4th
Edition. Edited by H . Kropf. Thieme, Stuttgart 1988. Part
1: xliv, pp. 1-990, hardcover, ISBN 3-13-218304-0; Part
2: xx, pp. 991 -1768, hardcover, ISBN 3-13-218304-0;
price for Parts 1 and 2: DM 2200.- (subscription and
pre-ordered price: D M 1980.-)
The fourth edition of “Houben-Weyl” began to appear in
1952 with Volume VIII and the article “Herstellung und
Umwandlung von Peroxyden”, by R. Criegee. The topic
which could then be reviewed in 74 pages by one author has
now grown to a two-volume work whose contents list alone
Angen.. Chem. Inl. Ed. EngI. 29 (1990) No. 3
consists of 57 pages. In this connection it is interesting to
read in the preface which E. Miiller wrote for Volume VIII:
“It is planned to complete the new work, consisting of about
14 volumes of 700 pages each, over a four-year period.”
Evidently it was not then foreseen that in 34 years time there
would be 67 volumes, together with indexes and supplementary volumes.
Despite the large number of contributors to Volume El 3
(30 authors), the editor H. Kropf has managed to achieve a
very uniform style of presentation which is in keeping with
the high quality of this standard work. The new volumes are
also commendably up-to-date: the literature up to 1987 has
been covered, and even some 1988 references are included
(the volumes appeared on 1 December 1988). The nomenclature is mainly in accordance with the IUPAC rules. Alongside the physical data in SI units the values in older units
have also been included in some cases; this unnecessarily
increases the size of the tables, for example where all the
energy data are given both in kJ and (in parentheses) in kcal.
However, listing distillation pressures in kPa could lead to
mistakes in converting to more familiar units, resulting in
delayed boiling or other accidents, and in this case, therefore,
all the values have been given in torr (with the SI units, kPa,
in parentheses in this case).
The arrangement of the subject matter essentially follows
the usual pattern adopted in “Houben-Weyl”. The first volume, which is the larger of the two, contains an introductory
chapter and preparative methods (Part A). The second volume contains transformations of peroxides into other compounds (Part B), peroxy compounds as reagents (Part C),
and analysis (Part D). The whole work is rounded off by a
general section (classification, structure, thermochemical
data, naturally occurring substances, safety aspects and toxicology), which precedes Part A, and a comprehensive index
at the end of Volume 2.
The classification of peroxy compounds given in the introductory chapter contains a degree of arbitrariness. According to this, peroxy compounds contain the characteristic
group -0-0-,which, in organic peroxides, is attached
through at least one carbon atom (or through a heteroatom
X bonded to a carbon atom). As a result of this definition,
carbonyl oxides are not counted as peroxides, and they are
not covered. However, organo-heteroelement peroxides are
included only in cases where the carbon is o-bonded. Consequently the important metalla-dioxiranes are not covered
(p. 956). On the other hand, the dioxiranes which are
analogous to metallacycles are included, even though these
are isomeric with the carbonyl oxides (and related to them in
chemical properties). A somewhat more pragmatic definition of peroxides would definitely have helped here.
In the first, introductory, chapter the newer methods of
“experimental computer chemistry” are treated too briefly,
even for a work in which the emphasis is on preparative
methods. A sentence such as “Theoretical calculations gave
values ranging from 80 to 180O, depending on the method of
calculation (CNDO, INDO, MINDO, MNDO, ab initio,
4-31 G)...” certainly does not do justice to the enormous
power of modern theoretical methods. In the area of peroxides especially, there are many instances where structures
first arrived at by calculation have later been confirmed in an
impressive way by experimental results.
Notable features of the general section are the newly revised thermochemical tables, and the chapter on safety aspects. This short and lucidly written chapter should be on
display in every laboratory where peroxides are used.
Part A which follows, dealing with methods of preparation, is the core of the whole work. In the familiar style of
$) VCH Verlugsgesel1,~chufi
’ mhH, 0-6940 Weinhelm, 1990
OS70-08233/90/0303-0327S 02.50/(1
“Houben-Weyl” it details a wealth of general and specialized
preparative methods, including yields, melting or boiling
points, and information about the properties of the compounds. This section is a mine of information, and in looking
up a particular compound or experimental recipe one is continually tempted to browse on adjacent pages. Part A is
arranged according to compound classes, starting with alkylhydroperoxides and continuing through to organotrioxides
and -tetroxides. A detailed index enables one to easily find
individual compounds, and the arrangement under compound classes also makes it possible to quickly locate functional groups, in cases where one is concerned with variations in the peroxide group. In a work as large as
“Houben-Weyl”, however, it would be useful to have an
index in the form of a computer data base (as in Beilstein),
which would allow one to search for particular structural
units. The general section of the subject index is quite pathetic. Under heading F, “General terms, named reactions, compound classes, trivial names”, we find a more or less arbitrary selection of terms, consisting of only eight pages of the
lengthy 176-page subject index. Important reactions such as
the Criegee rearrangement and the Sharpless epoxidation are
not included in this section, for example.
Part B deals with reactions whereby peroxides are converted into non-peroxide containing products. The topic is treated under nine reaction type headings: thermal reactions, catalytic reactions (catalysis by metals, bases and acids),
photolytic and radiolytic reactions, rearrangements, reductions, oxidations and lastly a short separate chapter on
organohydrotrioxides in the ozonolysis of C-H sp3 bonds.
After discussing the general mechanisms, specific examples
are given, often in the form of tables. The treatment of rearrangements in a separate chapter leads to some overlapping
with material in other chapters of Part B, but in view of the
importance of many of these reactions (e.g. the Hock and
Criegee rearrangements) this is justified. However, one
searches in vain here for the Baeyer-Villiger reaction; in-
stead this has been banished to a half-page paragraph on
page 862.
The many different methods whereby peroxy compounds
are used as reagents in organic chemistry are described in
Part C. This part is a continuation of Section l a (Peroxy
Compounds as Oxidizing Agents) in Volume IV of the Handbook, published in 1981, and it therefore covers only the
more recent literature. However, as the arrangement of the
topics is identical to that in the 1981 treatment, it is easy to
refer back to the earlier literature. The reactions described
here range from the use of “exotic” peroxides such as the
dioxiranes for the hydroxylation of unactivated CH bonds to
some very detailed chapters on the use of transition metal
catalysts. In particular the enantioselective Sharpless epoxidations have been given a considerable amount of space in
view of their importance.
Volume E l 3 concludes with the excellent Part D, which
has the simple title “Analysis”. Everyone who has ever
searched through the literature for spectroscopic data on a
group of compounds will appreciate the value of the tables
and the large compilation of data given here. All the analytical methods that are important for elucidating the structures
of peroxides are represented, from IR spectroscopy through
NMR spectroscopy (‘H, I3C, ” 0 ) to mass spectrometry.
Wet chemical methods for quantitative analysis and chromatographic methods are also described.
Volume El3 of Houben-Weyl will have a place in every
well-equipped chemistry library. Critical reviews of the literature on specialist topics such as this make an important
contribution towards maintaining a perspective over the tide
of publications which continues to grow exponentially.
Good workmanship has its price, and when one considers
how often Houben-Weyl is referred to, there can be no doubt
that it is a worthwhile purchase for every library.
Wo(framSander [NB 996 IE]
Organisch-chemisches Institut
der Universitat Heidelberg (FRG)
Regrswred names. rradrmorks. ctc used m iht.r,owmd. even when not markcd as such. ore nor 10 be considered unproircied by low.
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Angew. Chem. lnt. Ed. Engl. 29 (1990) N o . 3
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