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Book Review Short-Lived Molecules. By. M. J. Almond

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Chapter I has been included in the book as an addition to
the conference papers. This reviewer was unable to understand the colored “computer pictures” that are intended to
represent hydrophobic and hydrophilic surfaces of sucrose,
and they seem superfluous. The six chapters that follow are
concerned with the disaccharide sucrose. The first of these
describes the esterification and chloride substitution of different OH groups to produce nonionic surfactants and
sweeteners. Here we come across the first errors. On page 39
the compound under discussion is D-galacto-sucrose, but the
formula given is that of D-glUCo-SUCrOSe;on page 46 the formula shown is not that of the sweetener aspartam, as the
caption claims. Chapter 3 describes, with the help of diagrams, the enzymic conversion of sucrose to isomaltulose
and higher oligosaccharides using immobilized fructosyltransferases, then goes on to discuss the extraction and uses
of 5-hydroxymethylfurfural and levoglucosan. Unfortunately some formula errors have also crept into this chapter
(p. 75). In Chapter 4 the synthesis and applications of sucrose-methacrylate gels and sucrose-formaldehyde resins are
discussed. One of the uses of these products is for immobilizing and stabilizing transition metal complexes and photoreactive components. It is also suggested that they could be
used as drug carriers. In this chapter we also find (on p. 102)
a pentavalent carbon atom! Chapter 5 gives a brief account
of methods for synthesizing sucrose sulfates. Chapter 6 is a
very instructive and competent description of the chemical
and enzymic conversion of glucose to various I-O-CZ-D-gIycopyranosides for the production of surfactants and polymerizable vinylsaccharides. Chapter 7 is a clearly written account of the detailed process for the enzymic modification of
sucrose.
Next Chapter 8 briefly discusses the microbiological production of polyfructose and its potential use as a carrier
material for flavorings and colorants. Chapter 9 gives a detailed account of the history of the disaccharide leucrose,
from its discovery and structure determination to its production by a microbiological process and its use as an odor
additive in food products. In contrast, the description of
methods for obtaining poly-, oligo-, and monosaccharides
from sugar-beet pectin is of a very general nature.
In Chapter 11 attention is drawn to the potential uses of
the cheaply available saccharides glucose, fructose, lactose,
and isomaltulose for industrial-scale syntheses. The chapter
contains a number of serious printing errors that need to be
corrected. For example, on page 213 the acetylation of Dfructose and ring-opening with PCl, suddenly results in the
appearance of a benzoylated fructose derivative. Moreover,
the continuation from page 213 is found on page 215, and
from here one goes to page 214 (confusing); also formula 17
on page 217 needs to be corrected. The chapter continues by
describing the synthesis of natural products from carbohydrate precursors, with a few examples. The extensive bibliography to this chapter might also have included a reference
to the article by A. Vasella in Modern Synthetic Methoh 1980.
The next three chapters are concerned with the use of
hydrogen fluoride in carbohydrate chemistry and with a few
newer methods for the selective oxidation of D-glUCOSe and
of poly- and oligosaccharides, e.g. cyclodextrins. Chapter 15
describes the synthesis of vinyl-substituted sugars and their
polymerization to polyvinylsaccharides. The potential applications of these interesting polymers remain to be explored.
Lastly, Chapter 16 discusses the possibility of using sucrose
as a starting material for the manufacture of dyes, pigments,
and carbohydrate-modified organic conductors.
Leaving aside some printing errors and mistakes in diagrams that could have been avoided, this book gives a good
362
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VerlagsgeseNschaJimhH, W-6940 Weinheim, 1992
and informative account of the potential uses of sucrose,
leucrose, and glucose as organic raw materials, more especially by virtue of the extensive bibliography provided. Also,
by reading selected chapters, industrial chemists working in
this area will find stimulating ideas for the increased exploitation of carbohydrates.
Reinhold Oehviein
Ciba-Geigy
Basel (Switzerland)
Short-Lived Molecules. By M . J. Almond. Ellis Horwood,
New York, 1990.194 pp., hardcover $59.95.-ISBN 0-13798554-1
This book is intended for qualified chemists who do not
have a detailed knowledge of the subject described by the
title; the readership envisaged ranges from advanced chemistry students to chemists already engaged in research. In
particular it is claimed to be of interest to materials scientists
in industry, to readers whose work is concerned with catalysis and with photochemistry, and to those with interests in
high-temperature processes.
The relatively small size of the book means that the treatment of the subject must be limited to a few examples, and
the same also applies to the choice of material and the way
in which it is treated. Thus the book claims to be no more
than an introduction to the chemistry of short-lived
molecules. The author has taken account of this by including
a list of references at the end of each chapter, covering published work up to 1988. A noteworthy feature is a systematic
compilation of the most important review articles published
between 1978 and 1988; this fills in most of the gaps that the
book itself has unavoidably had to leave.
After an introduction the author briefly describes most of
the experimental techniques now commonly used for generating, detecting, and characterizing short-lived molecules
(evaporation, sputtering, flames, shock waves, photolysis,
flow systems, matrix isolation techniques, trapping experiments). The literature citations refer the reader on the one
hand to fundamental papers on individual techniques, and
on the other hand to published work breaking new ground
at the forefront of developments in modern experimental
methods.
The chapter on the photochemistry of metal carbonyl
compounds is the longest in the book (35 pp., 41 references).
As an especially important example the photosubstitution of
ligands in complexes of the type M(CO), (M = Cr, Mo, W)
is described in considerable detail, and some problems arising with particular methods of investigation are also discussed. This is followed by an account of the knowledge that
has been gained, mainly by matrix spectroscopy, about the
short-lived carbonyl complexes that can be generated from
various stable precursors (Fe(CO), , Mo(CO),, Mo(CO),,
Mo(CO), etc.) by splitting off one or more CO ligands. This
chapter ends with some considerations regarding multinuclear complexes, and complexes containing CO-related ligands
such as NO, ethene, and cyclopentadienyl. The rest of the
chapters are concerned with the reactivity of free metal
atoms, the chemistry of divalent silicon, aspects of organic
photochemistry, high-temperature molecules, ions and radicals, routes to inorganic materials, and the chemistry of the
atmosphere and interstellar space.
At first sight this choice of topics seems rather arbitrary,
and probably reflects the personal preferences of the author
as a guiding principle. However, one can accept this in view
0570-0833/92j0303-0362$3.50+.25/0
Angew. Chem. In(. Ed. Engl. 31 (1992) No. 3
of the aim set out in the introduction, which is to give a
selective overview of the field. A similar situation is found
with regard to the choice of material within each chapter. In
every case one could have made a different choice which
would have been at least equally good, and many topics are
only touched on very briefly. For example, in the final chapter there is no mention of the buckminsterfullerenes (C60and
higher homologues),'*' as important forms of interstellar
carbon and constituents of carbon black; however, the
manuscript was in preparation at a time before the critical
voices doubting this interpretation of the then available spectra had been completely silenced, and one can therefore understand the reasons for the omission.
Altogether the book contains such a wealth of stimulating
ideas that the reader whose interest goes deeper is unlikely to
be content with the text itself; the references provide easy
access to material for more detailed study. Thus the book is
a working guide rather than a textbook, and from this standpoint T found it enjoyable reading, and can therefore recommend it for the readership envisaged by the publishers. It
would be useful for university and research institute libraries
to have copies of the book so that it would also be easily
accessible to students.
Ulrich Zenneck
Institut fur Anorganische Chemie
der Universitat Erlangen-Nurnberg (FRG)
Frontiers in Supramolecular Organic Chemistry and Photochemistry. Edited by H.-J. Schneider and H . Diirr. VCH
Verlagsgesellschaft, Weinheim/VCH Publishers, New
York, 1991. xii, 485 pp., hardcover DM 196.00.--ISBN 3527-28016-210-89573-951-8
This book contains twenty articles which, except for the
chapters written by the two editors, are based on papers
presented at the Workshop on Supramolecular Organic
Chemistry and Photochemistry which took place at the end
of August 1989 in Saarbriicken, Germany. The main focus of
interest here lies not in the individual molecules but in the
association of molecules. The activities of the individual research groups in the area of supramolecular chemistry are
aimed not only at gaining a deeper understanding of biological systems but also, most importantly, at developing new
materials and technologies. In this book (p. 25) Lehn defines
the goal as: ". . . strategies toward properties and functions
rather than toward structures.. .". The topics covered in this
book are concerned with both aspects: they range from the
design of ligands and their synthesis, and a description of the
formation of complexes containing these ligands, through to
the photochemistry of biological systems. The arrangement
of the book's contents also essentially follows this pattern.
In the first chapter (pp. 1-28) Jean-Marie Lehn reviews
the work of his group, from the start of their investigations
of molecular recognition through studies of structures with
electronic and ionic conductivity up to work on information
and signal processing and molecular self-organization. This
is followed by a series of chapters dealing with problems of
host-guest interactions, as follows : selectivity and complementarity in molecular recognition, Schneider, pp. 29- 56 ;
receptors of the calixarene type, Ungaro, pp. 57-82; metallomacrocycles as host compounds for neutral guests, Rein
[*I
See J. F. Stoddart. Angew. Chem. 1991, 103, I t -12; Angew. Chem. In(. Ed.
1991. 30. 70-71.
Angew. ChPm. Inr. Ed. Engl. 31 (1992) No. 3
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houdt, pp. 83-108; the design and synthesis of a biotin receptor, determination of association constants in host-guest
complexes, Wilcox, pp. 123-144; azacyclophanes, Murakami, pp. 145-166. The main emphasis is also on synthesis in Stoddart's contribution (pp. 251 -264); here, however,
in catenanes and rotaxanes one is dealing with noncovalent
bonding of a different kind.
Czarnik and Diederich describe some real applications.
Czarnik (pp. 109- 122) uses changes in the fluorescence
properties as a method of analysis in the formation of chelates
by anthracene derivatives, while Diederich (supramolecular
catalysis, pp. 167- 192) has not only used his cyclophanes for
binding substrates but has also developed them into catalysts, e.g. for the condensation of benzoin or for the oxidation of aromatic aldehydes.
In the second part of the book the discussion of supramolecular systems is extended beyond host-guest complexes,
which are made up of only a few molecules, to micelles,
vesicles, membranes and various other systems, many of
which have liquid crystalline properties. The topics dealt
with are helical clathrates formed by inclusion in amylose
(Hui, pp. 203 -222), transport through channel-containing
membranes (Menger, pp. 193-202), and self-organizing
membranes (Fuhrhop, pp. 223 -250).
The final part of the book deals with photochemistry in
supramolecular structures, i.e. with those photochemical
and photophysical properties that distinguish supramolecular structures from the individual molecules of which they
are formed. The discussion is mainly concerned with fluorescence and electron transfer phenomena. The ultimate objectives of these studies, for example economically viable processes for the photochemical breakdown of water or the
fixing of CO, or nitrogen in nonbiological systems, are
still far from being attained. These contributions should
therefore be regarded as more in the nature of progress reports.
In the area of photochemistry the systems discussed again
include complexes made up of a small number of molecules,
but also in addition liquid crystals, micelles and biological
materials. Thus the topics covered include the photochemistry and photophysics of anthraceno-crown ethers (BouasLaurent, pp. 265-286) and of ion pairs and coordination
compounds (Balzani, pp. 371 -392). Schaffner discusses the
photophysics and photochemistry of the biliprotein chromophore with regard to its protein matrix (pp. 421 -452).
Ringsdorf describes the photoinduced structural changes
that occur in some organized supramolecular systems, most
of which are liquid crystalline (pp. 311 -336), and Willner
deals with photoinduced electron transfer in systems of this
type (pp. 337-370), whereas Braun discusses oxidation reactions in microheterogeneous media (pp. 393-420). De
Schryver describes the use of fluorescence measurements for
characterizing micelles. The photochemical part concludes
with a chapter on supramolecular photosensitizers (based on
ruthenium) for nonbiological photosynthesis (Diirr,
pp. 453-476).
Altogether this book is an excellent collection of papers
from the Saarbrucken Workshop, and it summarizes the latest developments in a number of different areas that come
under the general heading of supramolecular chemistry. The
layout of the text is clear and systematic, and there are plenty
of figures, some of which are in color. Regrettably, however,
the high price will be an obstacle to reaching a large readership.
Ulrich Liining
Institut fur Organische Chemie und Biochemie
der Universitat Freiburg (FRG)
~rlagsgesell.~chufl
mbH. W-6940 Weinheim, 1992
0570-0833/92/0303-0363$3.50+ .25/0
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