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Book Review Nitroazoles. The C-Nitro Derivatives of Five-Membered N- and N O-Heterocycles. By J. H

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has not been synthesized by this method, p. 294, line 5 :
(CO),, p. 298, Eq. 5.31: the product is [CpIrHL,]@, p. 317,
middle left: negative charge missing, p. 321, Eq. 5.67:
should be CSMes, p. 380: C6Me6Ru-not Cp*Ru, and p.
890, Eq. 19.19: Mo02(acac), instead of Mo(O,)(acac),.
Also it is regrettable (and a little disappointing) to find that
the historical milestones are in some cases viewed through
“USA-tinted’’ spectacles. For example, in the chapter on
“Historical Perspectives” there is no mention of Walter
Hieber and his pioneering work on metal carbonyl complexes, and no reference is made reflecting the very important publications by Dewar, Chatt, and Duncanson on
bonding in olefin-metal complexes. Again, the false impression is given that the structure of ferrocene was correctly proposed only by Wilkinson, Rosenblum and Woodward. whereas it also came simultaneously from Fischer
and Pfab. Other omissions: when mention is made of the
Monsanto process, why not also of the Wacker process,
which is equal in technological importance? When, in connection with the discovery of the intermolecular oxidative
addition of saturated hydrocarbons to transition metals,
mention is correctly made of Bergman, why not also of
Graham in the same breath? An opportunity has been missed here to present a n objective picture (acceptable
throughout the world) of the historical development of the
subject; this is especially regrettable when one considers
that students also need to be educated in the history of
However, taken as a whole the positive impressions
given earlier outweigh these criticisms, and the textbook
can be strongly recommended for reading by advanced
students. Fortunately the price is also reasonable, something which is nowadays much appreciated.
Helmut Werner [NB 885 IE]
Institut fur Anorganische Chemie
der Universitat Wiirzburg (FRG)
Nitroazoles. The C-Nitro Derivatives of Five-Membered Nand N,O-Heterocycles. By J. H. Boyer. VCH Publishers,
Deerfield Beach 1986. xv, 368 pp., bound, DM 185.00.ISBN 0-89573-138-7
In the fifties and sixties, nitro compounds interested
chemists primarily as propellants and explosives. Since
then, however, this most easily introduced of functions, the
nitro group, has been recognized to have an activating effect on numerous organic reactions, and to be easily convertible into other useful nitrogen functional groups. This
is emphasized by the commencement of a new series,
“Organic Nitro Chemistry”, of which Volume 1, “Nitroazoles”, has now appeared.
The 368-page work is divided into sections on nitration,
chemical, physical (spectroscopic) and biological properties, reactions, and references. Inside this framework, nitropyrroles, nitroimidazoles, nitropyrazoles, nitrotriazoles
and nitrotetrazoles are described, as are the nitro derivatives of isoxazoles, oxazoles, oxadiazoles and the heterocyclic systems derived from these by annelation of further
rings. The table of contents, though very detailed, could
have been more clearly laid out.
The bibliography contains 1501 original citations, and
an extensive list of references is also appended to each
chapter (the names of German, Austrian and Swiss workers are unfortunately often misquoted). While many classic
heterocycle monographs, series, reviews, and articles are
cited, one seeks in vain for the newest standard work,
Angew. Chern. Int. Ed. Engl. 27 (1988) No. 7
“Comprehensive Heterocyclic Chemistry” (published
1984). The author earns special praise for having analyzed
and evaluated the overwhelming number of Soviet publications on the subject of nitroazoles. In doing so, he has
made an area that has been intensively studied in the Soviet Union available in the West for the first time.
The first five chapters deal extensively with the most favorable reagents and methods for nitration of the various
heterocycles. Where direct nitration is difficult, ring closure or ring transformation reactions often give the desired
result. The sections on chemical reactivity include alkylation, acylation and arylation at both nitrogen and carbon,
halogenation, reduction (including electrochemical methods), oxidation, decarboxylation, rearrangements, exchange of the nitro group for side-chains, nucleophilic and
electrophilic substitution and addition, metallation, ring
cleavage, free radical reactions, thermo- and photochemistry (degradation) and glycosylation. For important key
reactions the yields are always reported, and stereochemical aspects are taken into account. Biotechnological conversions of amino- into nitroheterocycles are also described (p. 95). The sections on physical properties offer
much information, and the biological properties of the nitroazoles and their derivatives are described in separate
While the computer-drawn structural formulas are clear
and informative in every respect, for a book in this price
range they display numerous flaws and deficiencies. Bond
lengths are too short or too long, heteroatoms are superimposed on bonds, substituents are cramped, rings are set out
crookedly (e.g. pp. 190, 191, 227), carbonyl groups are distorted (p. 331), and substituents are twisted (p. 131). Many
less expensive textbooks are able to offer more than this!
The consistent numbering of formulas with the chapter
number as prefix is very practical.
All in all, this monograph is a valuable addition to the
chemical literature, and is highly recommended for anyone
who comes in contact with the topic of azoles.
Heinrich Wamhoff [NB 888 IE]
Institut fur Organische Chemie und Biochemie
der Universitat Bonn (FRG)
Biohalogenation. Principles, Basic Roles, and Applications.
By S . L. Neidleman and J. Geigert. Ellis Horwood, ChiChester 1986. 203 pp., bound, L 25.00.--ISBN 0-85312984-3
Halogens and halogen compounds play an important
role in many areas of chemistry. It therefore seems at first
surprising that not very much is known about halogenation
in biochemistry. Certainly many halogen compounds occur in nature, but there is no precise knowledge about their
formation and importance. It has only recently become
possible to detect and characterize halogenating enzymes
in prokaryotic organisms, whereas they had already been
recognized long before this in eukaryotic organisms (molds
and algae). These enzymes were given the name “haloperoxidases”, since in addition to halide ions they also
need hydrogen peroxide in order to halogenate an organic
The present state of knowledge on biohalogenation is reviewed for the first time in the book by Neidleman and Geigert. The nine chapters deal with some of the halogen
compounds which occur in nature, the organisms producing them, the halogenating enzymes that have so far been
isolated, and their importance to the organisms concerned.
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nitroazoles, book, membered, five, nitra, heterocyclic, review, derivatives
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