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Book Review The Chemistry of the Quinonoid Compounds. Vol. 2. Parts 1 and 2. Edited by S. Patai and Z. Rappoport

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To sum up it is appropriate to quote from the preface of
“Angular Momentum”: “This is not the first book on angular momentum theory, but it differs from others in the emphasis placed on making it a learning text for those with a
minimum background in quantum mechanics. It also differs
in the choice of examples that are drawn almost entirely from
atomic and molecular phenomena. I believe that it is not
possible to present this material too simply to anyone learning angular momentum theory for the first time. Consequently, many intermediate steps are left in the text, which,
to the initiated, may appear inelegant, if not annoying. At
the same time this text serves a secondary purpose of being
a reference work; the vast majority of formulas needed to
solve any problem in angular momentum theory are contained in this book”. It only remains for me to add that the
book is strongly recommended as a textbook for students
and prospective researchers (and is very sensibly priced!). I
hope that it will run into many printings.
Martin Quack [NB 972 IE]
Laboratorium fur Physikalische Chemie
der Eidgenossischen Technischen Hochschule
Zurich (Switzerland)
Chemiluminescence.
ChichesterjVCH
Publishers, New
DM 280.00.ISSN 0930-3367.
By A . K. Campbell. Ellis Horwood,
Verlagsgesellschaft, Weinheim/VCH
York 1988. 608pp., hard cover,
ISBN 3-527-26342-X/0-89573-501-6;
In separate chapters, the author covers the history of
chemiluminescence, detection and quantification, bioluminescence, the need for chemiluminescence analysis,
measurement of enzymes and metabolites, ultraweak chemiluminescence, indicators for inorganic ions, an alternative to
radioactive labels, energy transfer, and “hills and horizons.”
Five appendices follow: a glossary, names of luminescent
organisms, instructions for finding luminescent organisms,
chemiluminescence demonstrations, and commercial sources
of equipment.
The book contains a very large amount of information,
but concentrated on the biological aspects. The subtitle on
the cover “Principles and Applications in Biology and Medicine” is a better description. The historical aspects of the
subject are developed in considerable depth, and the tabulation of the numerous units for light in Chapter 2 is particularly helpful. The text and figures are free from typographical errors.
The book unfortunately has a number of faults. In spite of
the fact that chemiluminescence is my own specialty, I found
the book rather tedious to read. On page 233 we are told that
Mexican women use bioluminescent adornments in headwear. The same fact appears in a table on page240, and
again in the text on page 241. Lucigenin appears in a table on
page 247 as an indicator of “reactive oxygen metabolites”,
again on page 302 in a table on limits of detection of oxygen
metabolite measurement, with no data entry, and in a third
table (page 364) as an indicator of reactive oxygen metabolites 0; and ‘0,. In most of the tables there is only one bit
of information per entry. Aside from redundancies, Campbell seems unwilling to allow the reader to use his intelligence
and imagination to figure out anything for himself. Half of
page 242 is a photographed control experiment that shows
absolutely nothing. In the appendix on collecting specimens
at night, he gives a useful tip that a squirt of KCI solution will
stimulate organisms to emit light, but then spoils it by dutiAngew. Chem. Int. Ed. Engl. 28 (1989) No. 7
0 VCH
fully itemizing a shovel, a bucket, and a flashlight as necessary equipment for any nocturnal expedition.
The author’senthusiasm for thesubject isquiteevident, and
one is inclined to blame the editors for not showing a more
businesslike hand in dealing with numerous artistic literary
digressions into topics ranging from children’s nursery
rhymes to Welsh nationalism. Since footnotes do not appear
in the text, it is at times difficult to separate fact from entertaining speculation. The encyclopedic scope of the book is
probably best suited for biochemists and medical people with
limited background who are interested in entering the field.
David Mendenhall [NB 953 IE]
Department of Chemistry and Chemical Engineering
Michigan Technological University
Houghton, MI (USA)
The Chemistry of the Quinonoid Compounds. Vol. 2. Parts 1
and 2. Edited by S. Patai and 2. Rappoport. Wiley,
Chichester 1987. Part 1: xiv, pp. 1-878, hardcover,
E 175.00.--ISBN 0-471-91285-9; Part 2: xiv, pp. 8791711, hardcover, E 175.00.--ISBN 0-471-91914-4 (2-volume set E 325.00.-ISBN 0-471-91916-0)
The first “Patai” on quinones appeared in 1974. Since
then the preparative chemistry of quinones has been described in “Houben-Weyl” in 1977 and in 1979, whereas a
recent account of naturally occurring quinones is available in
Volume 3 of Thomson’s series. Thus, after nearly 15 years,
the new “Patai” presents a much needed survey that covers
the broad spectrum of quinone chemistry. These books are
timely and most useful for everyone who is concerned with
quinonoids in research and teaching.
Chapter 1 is a general introduction into the theoretical
chemistry, such as orbital calculations, spectroscopy and reactivity of simple quinones, quinonemethides, quinoneimines and thioquinones. Three chapters on analytical aspects
follow: the first one contains numerous references on NMR,
IR, and UVjVIS spectroscopy, as well as on chromatographic and electrochemical methods. Unfortunately actual results
are mentioned in only a few instances, and the reader will
find it necessary to consult the library in order to uncover the
essential information hidden in Chapter 2. Some fundamental publications by Sealy et al. on ESRiENDOR spectroscopy
appear to have been ignored. Chapter 3 contains numerous
data on electron impact ionization mass spectroscopy of anthraquinones, and Chapter 4 deals with the chiro-optical
properties (ORD and CD) of chiral quinones that are of
interest primarily to the natural products chemist.
The physical chemistry of quinones is described in five
chapters. The impressive development in the field of photoelectron spectroscopy is reflected in Chapter 5, which contains a thorough discussion of quantum chemical calculations and many results in tabular form. This chapter also
includes three-, four-, and five-membered ring systems as
well as heteroquinonoids. Chapter 6 is a more specialized
account of the photo-, thermo-, and piezochromism of bianthrones and bianthrylidenes. Chemiluminescence follows
in Chapter 7. A comprehensive account of the electrochemistry is given in Chapter 12. An informative review on
the reactions and spectroscopic properties of free radicals is
found in Chapter 14, which also contains some examples of
biochemically important quinonoids.
The remarkable progress in the synthesis of quinonoid
compounds is summarized in Chapter% More than 500
VerluRsRL.sell.~~hajt
mhH,I.-6940 Weinheim,I989
0570-0833/89/0707-0933 R 02.50j0
933
original articles are covered in 162 pages, and the subjects are
properly ordered under methodological subheadings, such
as oxidations, annulations, cyclizations and condensations.
Organometallic chemistry is covered as well as protective
group chemistry with silylated quinones. One third of the
chapter deals with the synthesis of naturally occurring
quinones, and some of the reactions discussed earlier are
repeated here. Nevertheless, this section illustrates the preparative aspects in a very informative way.
The second large chapter on preparative chemistry (Chapter 11, 182 pages, nearly 800 references) summarizes the use
of quinones in organic synthesis. Vinylogous additions, reactions at the carbonyl group, cycloadditions, alkylations and
substitutions are discussed comprehensively. Numerous examples are given concerning the use of quinones in heterocyclic synthesis. The biochemist will find many hints to
analogies of quinone reactions in biological systems. Preparative and mechanistic photochemistry is reviewed in Chapter 13, which contains an orderly arranged survey of the
reactions and results, including many tables. A more specialized account of dehydrogenation reactions of quinones in
Chapter 23 deals mostly with DDQ. Many interesting examples of allylic and benzylic oxidations are cited.
Chapter 19 illustrates the importance of isotopically labeled quinones in mechanistic and biosynthetic investigations. The detailed, handbook-style listing of various compounds and their synthesis is most appreciated by those
concerned with the preparation and use of labeled quinones.
However, some of the examples seem to be unnecessary, such
as the synthesis of [7-14C]-geraniol and [7c~-‘~C]-methoxycephalosporin. Also the rather extensive description of general tracer methodology is superfluous. Some overlap exists
in the contents of Chapters 19 and 22. The latter, entitled
“The Biochemistry of Quinones”, actually contains a very
thorough and informative review of the biosynthesis of
quinones, divided into sections on polyketides, shikimate
metabolites and isoprenoids. Further sections deal with the
metabolization of quinones into other natural products, e.g.
aflatoxins, and with the role of vitamin K in blood clotting.
Several classes of quinonoid compounds are discussed
under preparative, mechanistic o r theoretical aspects in eleven chapters. The chemistry of o-quinonoids is presented in a
rather lengthy way in Chapter9. A discussion on mquinones and related non-Kekule structures follows in
Chapter 10. The preparation and reactions of quinone bisand monoketals is described in a clear style and with many
tables in Chapter 15. Chapter 16 deals with quinhydrones
and semiquinones, including their metal complexes, and
there is a partial overlap with Chapter 14. Again, redox potentials, pK, values and UV spectroscopic data are listed in
tabular form. Some biologically important semiquinones are
mentioned.
The synthesis and reactions of heterocyclic quinones are
described in Chapter 17, which contains many references to
organometallic reagents. Some overlap exists with the contents of Chapter 8, e.g. the synthesis of the niitomycins. The
following Chapter 18 on polymerization reactions deals
almost exclusively with substituted p-quinodimethanes. It
includes an extensive compilation of data on the reaction
kinetics. The solid state photochemistry of tetrahydronaphthoquinones is described in the rather specialized Chapter 20. p-Quinoneimines, which are particularly useful in industrial applications as coloring materials, are discussed in
Chapter 21. Azulene quinones and polycyclic quinones, including annulenes and non-benzenoid systems, are found in
Chapters 24 to 26, where some overlap exists in the description of the theoretical aspects in Chapters 24 and 26.
934
(‘1
VCH VrrlagsgesellschuftmbH, 0-6940 Wnnhrirr. 1989
In summary, the new “Patai” presents an impressive collection of articles on nearly all aspects of quinone chemistry.
More than 4500 references covering the period between 1974
and 1986 have been evaluated. In accordance with the intention of the editors, the literature prior to 1974 is cited very
sparingly. Some subjects were not included in the collection:
there is no separate chapter on quinone methides. They are
mentioned, however, on several occasions throughout the
books. One would have liked to see a separate chapter on
quinonoid biopolymers and on chemical modifications of
various biopolymers by quinones, though some biochemically important reactions are mentioned occasionally.
The text is quite heterogenous with respect to style and
density of information. Some very specialized topics are distributed among some broad and general overviews. Eventually, an attempt to achieve more consistency in some chapters might lead to a smaller degree of overlapping. A further
suggestion to the editors is that each volume should include
a list of abbreviations. As it is now, searching for the meaning of abbreviations used in some chapters can become a
time-consuming task. The subject index is not extensive
enough, e.g. the key-word “daunorubicin” does not lead to
the important data in Chapter 14 (p. 893). The sequence of
chapters should be arranged more consistently with respect
to the general topics.
Technically, the books are thoroughly prepared. Only a
few errors o r sloppy formulations were noted (e.g., on p. 495
c,c- and t,r-2,4-hexadienes.. . should read: ZZ- and E E . . .;
p. 1301 : 25-iso-caproyl . . . should read 2 S-isocaproyl). Very
few corrections are necessary in the reaction diagrams and
formula schemes (e.g., p. 590, eq. 168: it is not evident from
the formulas that the oxidative deamination leads to a 2-keto
sugar which is then reduced to the 2-deoxy sugar shown;
p. 652, eq. 359: the formula of the butadiene derivative is
incorrect in the original paper; p. 681, eq. 452: the formula
of homophthalimide is wrong). According to the latest published work, the mechanism of the cytotoxic action of mitomycin on p. 1058 should be revised. Nevertheless, these are
minor mishaps which do not at all diminish the value of this
important volume. The “Quinone Patai” will find its place in
the libraries of most research and teaching institutions. Unfortunately, the high price is prohibitive for purchase by
individuals. The list of those who will greatly appreciate
these books includes scientists from the fields of physical and
synthetic organic chemistry, natural products and pharmaceutical chemistry, and, last but not least, organometallic
and biological chemistry.
Martin G. Peter [NB 944 IE]
Institut fur Organische Chemie und Biochemie
der Universitiit Bonn (FRG)
Principles of Organometallic Chemistry. 2nd Edition. By P.
Powell. Chapman and Hall, London/New York 1988. xv,
41 5 pp., paperback, L 13.95. -ISBN 0-41 2-27590-2. hard cover, L 13.95. -ISBN 0-412-27580-5
Anyone who, like this reviewer, was a chemistry student in
the early 1970s and was fascinated by the then still young and
rapidly developing subject of organometallic chemistry, will
clearly remember the first edition of this book, published in
1968 with four authors (G. E. Coates, M . L. H . Green. P.
Powell and K. Wade). That, together with its German translation published in 1972, was almost the only textbook on
organometallic chemistry tailored to the needs of students,
unless one was prepared to use the two-volume “Coates”.
0570-0833189/0707-c)934$02.50/0
Angrn. Chem. Int. Ed. EngI. 28 (1989) No. 7
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