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Book Review Protective Groups in Organic Synthesis. By T. H. Green

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BOOK REVIEWS
Chemistry of Coal Utilization, Second Supplementary Volume. Edited by M. A. Elliot, Wiley-Interscience, New
York 1981. 2374 pages, bound, $ 165.00.
The American “Chemistry of Coal Utilization”, a handbook that has already become a classic and that is certainly
unique in its scope and treatment of the material, has now
been updated by the appearance of the second supplementary volume, after the original two-volume work of 1945,
edited by H. H. Lowry, was first supplemented in 1963. As
in the case of the previous volumes, a committee of the
National Research Council of the U.S. National Academy
of Sciences assumed the sponsorship of the new supplementary volume which, under the new editor Elliot- Lowry
died ten years ago-includes contributions from 60 wellknown authors. In continuation of the earlier work, detailed information is given not only on coal chemistry in
the narrower sense but also, with the exception of mining
technology, on all technologies for the utilization and upgrading of coal and on the conversion of coal into energy,
fuels, and chemical raw materials. In spite of the primary
aim to take up the story at the point at which the review of
the first supplementary volume ended, i. e. essentially to
give a critical review of the literature between about 1958
and the second half of the seventies and to describe further
developments in this period, to a large extent the result has
been an almost textbook-like account rather more suitable
for advanced readers. Specifically, the 3 1 chapters deal
with the coal industry, coal research and development (an
overview written by the editor himself); coal resources
(only the deposits of the United States are treated in detail); origin, petrography, and classification of coal; physical properties of coal and coal products; mechanical properties; plastic properties; analysis of coal, trace elements,
and mineral constituents; chemical reactions and chemical
constitution of coal; transport, storage, and handling; preparation; briquetting ; pyrolysis and hydropyrolysis (3
chapters); solid pyrolysis products; coar tar (2 chapters);
coke-oven gas; combustion of coal (2 chapters); coal ashits effect on combustion; control of pollution from combustion processes ; gasification of coal (3 chapters); underground gasification of coal; liquefaction of coal (3 chapters); conversion of coal and coal gases into fuels, chemicals, and other products; and environmental, health, and
safety implications of increased coal utilization.
On the whole, it must be said that the compilation and
organization of the enormous volume of material has been
highly successful. Overlapping between individual chapters, unavoidable because closely related subjects are
treated by different authors, is kept to reasonable limits.
The reviewer is not in a position to judge to what extent it
has been possible to take into account the literature and all
the developments of the various technologies. After all, the
quality of the contribution depends in the final account on
the knowledge, experience, and carefulness of the particular author (information about the professional career and
the present position of each author is given by brief biographies at the beginning of the chapters). Apart from
some contributions from the United Kingdom, Australia,
640
and the German Federal Republic, the majority of the
chapters have been written by American authors. In reading some chapters one cannot quite escape the (subjective)
impression that the account, particularly of the economic
and technical developments, is frequently limited substantially to the situation in the United States. For example, in
Chapter 28 (Liquefaction Processes) all the American
processes for direct liquefaction of coal are described in
detail, whereas there is nothing about the corresponding
developments of the National Coal Board in the United
Kingdom and there are only a few lines on the IG-“Neu”
Process in Germany, by which is meant the new activities
in connection with the hydrogenation of coal, based on the
old IG process. A partial explanation for this shortcoming
may be that these European developments really started
up only in the mid-seventies, not long before the early editorial deadline (depending on the chapter, between August
1976 and the end of 1978). Other examples could be
quoted. Another point of criticism relates to the use of
units: it must be just as annoying for the English or American reader when, for example as on page 1782, temperatures are given in degrees Fahrenheit and enthalpies in
Btullb-mole in one place and four pages later the same author uses the units Kelvin and kcal/g-mole!
The extensive subdivision of the text by headings makes
for clarity, the graphic presentation including the figures
and tables is excellent, and the citation of references in
footnotes on the same page is exemplary. Small mistakes
and printing errors do not appear to exceed the usual quota. The subject index, however, leaves something to be desired.
All in all, this second supplementary volume in combination with the earlier work offers a unique compilation,
of inestimable value, of the scientific and technical literature on coal. No library should therefore delay in getting
this supplement to their “Lowry”. But even without the
earlier volumes, which, by the way, can still be obtained as
reprints, the book will be highly valuable for the interested
specialists, if not indeed indispensable.
Matthias W. Haenel [NB 562 I E ]
Protective Groups in Organic Synthesis. By T. H . Green.
John Wiley & Sons, Chichester 1981. xiii, 349 pp.,
bound, E 26.25.
Although the use of protective groups for the blockage
(deactivation and differentiation) of functional groups is
indispensable in many organic reactions, particularly in
special classes of substances such as the carbohydrates and
the amino acids, in the planning of a particular synthesis
one should always bear in mind that this advantage is accompanied by a drawback: Two additional reaction steps
Angew. Chem. In(. Ed. Engl. Z I (1982) No. 8
are usually necessary, for the protective groups must first
be introduced and then removed. A large number of protective groups have been proposed for a variety of purposes, differing in the nature of their introduction, their
differentiated removal, their stability to special reagents,
etc., and frequently capable of being used for only one
reaction step. Thus, recently, protective groups that can be
removed photochemically or electrochemically have been
called upon. The fact that, after the widely used book by
McOrnie (1973), another book on protective groups has
now appeared, in which the modern developments in this
field have been particularly taken into account, is highly
welcome.
A short introduction on the importance of protective
groups in organic chemical synthesis is followed by a description, in six chapters, of about 400 protective groups
for the important functional groups. The following protective groups are discussed in detail: monohydroxy compounds: substituted alkyl ethers (42), silyl ethers (12), and
esters (52); 1,2- and 1,3-diols: acetals and orthoesters (31);
phenols: ethers, esters, carbonates, carbamates, and sulfonates (32); carbonyl compounds : full acetals, thioacetals,
hemithioacetals, 0-substituted cyanohydrins, substituted
h ydrazones, imines, oxazolidines, imidazolidines, and thiazolidines (37). (The monoblockage of dicarbonyl compounds is also described here (7).) Carboxy compounds:
esters, amides, and hydrazides (63); thiols: thioethers (28),
thioesters (9), disulfides (2) and sulfenyl derivatives (2);
amines : carbamates, amides, imides, N-alkyl compounds,
aminoacetals, imines, enamines, N-metal compounds, and
N-heteroatom derivatives (91). There is no information on
the protective groups for olefinic double bonds.
For the individual protective groups the processes of
their formation and removal are described, always with
references to the literature and, wherever possible, with
special observations (range of application, stability, etc.).
No information is given on the availability or synthetic accessibility of the reagents used.
A particularly valuable feature of the book is Chapter 8,
“Reactivities, Reagents, and Reactivity Charts,” in which
the stability of many of the protective groups described in
the book with respect to 108 prototype reagents from 16
reaction areas (e. g . oxidation, reduction, and organometallic reactions) is summarized in tabular form. For example,
it can be deduced from the tables that tert-butyl diphenylsilyl ethers are still stable at pH 2-4, while the tert-butyl
dimethylsilyl ethers are already cleaved in this pH range.
Chemical Additives for Fuels. Developments since 1978.
Edited by M . T. Gillies. Noyes Data Corporation, Park
Ridge, New Jersey 1982. xii, 308 pp., bound, $ 48.00.ISBN 0-8155-0886-7
Separation and Preconcentration Methods in Inorganic
Trace Analysis. By J . Minczewski, J . Chwastowska, R .
Dybczynski, Translation Editor: M. R . Masson. Ellis
Horwood Ltd., Chichester 1982. xi, 543 pp., bound,
f 37.50.-ISBN 0-85312-165-6
International Series in Natural Philosophy. Vol. 103: Metal
Vapours in Flames. By C. Th.J. Alkernade. J . Hollander.
W. Snelleman, and P. J . Th.Zeegers. Pergamon Press,
New York 1982. xxii, 1033 pp., bound, $ 95.00.-ISBN
0-08-018061-2
Mikrobielle Gewinnung von Arzneistoffen. Pharmazeutische
Mikrobiologie. By D. Groger and S. Johne. AkademieVerlag, Berlin 1982. 266 pp., bound.-ISSN 0084-0963
Classical Mechanics. Vol. 1. By E. A. Desloge. John Wiley
& Sons, Chichester 1982. xviii, 507 pp., bound, L
29.50. --ISBN 0-47 1-09144-8
The Chemistry of Heterocyclic Compounds. Vol. 41: The
Pyrazines. By G. B. Barlin. John Wiley & Sons, Chichester 1982. xxi, 687 pp., bound, f llO.OO.-ISBN 0-471.38119-5
Triplet State ODMR Spectroscopy. Techniques and Applications to Biophysical Systems. Edited by R . H . Clarke.
John Wiley & Sons, Chichester 1982. v, 566 pp., bound,
f 43.75.--ISBN 0-471-07988-X
The book is arranged systematically; however, because
of the wealth of information, the reader will need some
time to become familiar with its use.
Advances in Heterocyclic Chemistry. Vol. 30. Edited by A.
R. Katritzky. Academic Press, New York 1982. ix, 408
pp., bound, $ 76.50.--ISBN 0-12-020630-7
This could have been avoided by selecting three to five
“standard protective groups” supplementing one another
for each of the individual functionalities, that would ensure success in 80-90Yo of the cases. It would then have
been possible to include experimental instructions for the
formation and the removal of these standard groups. Some
description of the elegant methods for the blocking and activation of functionalities, e . g . via S- or 0-acetals, would
also have been desirable.
Fourier, Hadamard and Hilbert Transforms in Chemistry.
Edited by A. G. Marshall. Plenum Press, New York
1982. xii, 562 pp., bound, $ 65.00.--ISBN 0-306-409046
In conclusion, the book will undoubtedly prove very
useful for the synthetic chemist both in industry and academic circles, and it can be expected to find wide use.
Lutz-F. Tierze [NB 568 IE]
Angew. Chem. Inr.
Ed. Engl. 21 (1982) No. 8
Surface Treatments for Improved Performance and Properties. Edited by J . J . Burke and V. Weiss. Plenum Press,
New York 1982. x, 224 pp., bound, $ 35.00.-ISBN 0306-40897-X
Charakterisierung von Kunststoffen mit physikalischen
Methoden. Verfahren und praktische Anwendung. By G .
KumpJ Carl Hanser Verlag, Miinchen 1982. 331 pp.,
bound, DM 78.00.-ISBN 3-446-13382-8
64 I
Carbocationic Polymerization. By J. P. Kennedy and E.
Marichal. John Wiley & Sons, Chichester 1982. ix, 510
pp., bound, E 55.50.-ISBN 0-471-01787-6
Gmelin Handbuch der Anorganischen Chemie. SpringerVerlag, Berlin 1982. 8th Edit.
Sn-Organotin Compounds. Part 9: Triorganotin-Sulfur
Compounds. xii, 276 pp., bound, DM 727.00.--ISBN 3540-93456-1
SC, Y, La-Lu-Rare
Earth Elements, Part c 4b. Data on
Individual Chlorides, xviii, 324 pp., bound, DM
876.00.-ISBN 3-540-93457-X
Te-Tellurium. Supplement Volume A 1 : Recovery.
Uses. Preparation. Nuclides. Atom. Molecule. xii, 173
pp., bound, DM 727.00.--ISBN 3-540-93448-8
Technische Chemie I. Grundverfahren. By W. Brotz and A.
Schiinbucher. Verlag Chemie, Weinheim 1982. xv, 380
pp., bound, DM 68.00.-ISBN 3-527-25852-3
Schmierstoffe und verwandte Produkte. Herstellung-Eigenschaften- Anwendung. By D. Klamann. Verlag Chemie,
Weinheim 1982. 220 pp., bound, DM 68.00.--ISBN 3527-25966-X
Farbstoffchemie. Ein Leitfaden. By P. Rys and H . Zollinger. 3rd revised edition. Verlag Chemie, Weinheim 1982.
xi, 200 pp., bound, DM 58.00.-ISBN 3-527-25964-3
Erbforschung heute. Edited by W . Klingmiiller. Verlag
Chemie, Weinheim 1982. 171 pp., bound, DM 38.00.ISBN 3-527-25939-2
Lecture Notes in Chemistry. Vol. 29: Unified Valence Bond
Theory of Electronic Structure. By N. D. Epiotis. Springer-Verlag, Berlin 1982. vii, 305 pp., bound, DM 52.50.ISBN 3-540-11491-2
Lecture Notes in Chemistry. Vol. 30: Qualitative ValenceBond Descriptions of Electron-Rich Molecules: Pauling
“3-Electron-Bonds” and bbIncreased-Valence”Theory. By
R . D.Hurcourt. Springer-Verlag, Berlin 1982. x, 260 pp.,
bound, DM 48.00.-ISBN 3-540-11555-2
Stereospecificity in Organic Chemistry and Enzymology. By
J . RCtey and J . A . Robinson. Verlag Chemie, Weinheim
1982. xii, 324 pp., bound, DM 138.00.-ISBN 3-52725905-8
Mikrobielle Proteingewinnung und Biotechnologie. 2. Symposium, 1980. GBF Monograph Series No. 6. Edited by
P. Prave, K . Schugerl, and H . Zucker. Verlag Chemie,
Weinheim 1982. xi, 262 pp., bound, DM 80.00.-ISBN
3-527-25967-8
The Chemistry of Pesticides. Their Metabolism, Mode of
Action and Uses im Crop Protection. By K . A. Hassall.
Verlag Chemie, Weinheim 1982. xiv, 372 pp., bound,
DM 148.00.--ISBN 3-527-25969-4
Beschreibung der Versuche mit der Luftkugel. By F. de
Saint-Fond. Edited by E. H. Berninger, G. Giesler, and
0. P. Kratz. Verlag Chemie, Weinheim 1981. 383 pp.,
bound, DM SS.OO.-ISBN 3-87664-052-0
Progress in Inorganic Chemistry. Vol. 29. Edited by S. J.
Lippard. John Wiley & Sons, Chichester 1982. v, 401 pp.,
bound. L 38.75.--ISBN 0-471-09370-X
Lehrbuch der Physikalischen Chemie. By G. Wedler. Verlag
Chemie, Weinheim 1982. xii, 914 pp., bound, DM
98.00.-ISBN 3-527-25880-9
The Literature Matrix of Chemistry. By H. Skolnik. John
Wiley & Sons, Chichester 1982. xi, 297 pp., bound,
L 23.50.-ISBN 0-471-79545-3
Aminosauren, Peptide, Proteine. By H.-D. Jakubke and H.
Jeschkeit. Verlag Chemie, Weinheim 1982. 505 pp.,
bound, DM 76.00.-ISBN 3-527-25892-2
Physikalische Chemie. Teil I: Atome, Molekiile, Kerne. By
G. M. Barrow. Revised by G. W. Herzog. Vieweg,
Braunschweig 1982. xi, 374 pp., bound, DM 26.80.ISBN 3-528-43512-7
Theoriewandel in der Wissenschaftsgeschichte. Chemie im
18. Jahrhundert. By E. Stroker. V. Klostermann, Frankfurt 1982. viii, 324 pp., bound, DM 68.00.-ISBN 3-46501497-9
Microemulsions. Edited by I. D. Robb. Plenum Press, New
York 1982. viii, 259 pp., bound, $ 35.00.-ISBN 0-30640834-1
Der Schutz wissenschaftlicher Forschungsergebnisse. By F.K. Beier and J. Straus. Verlag Chemie, Weinheim 1982.
viii, 116 pp., bound, DM 48.00.--ISBN 3-527-25940-6
Regisrered nomes. rrademorks. err. used in rhis journal. even wirhour specific indicorion rhereoJ are not io be considered mprorerred b j low.
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Angew. Chem. In!. Ed. Engl. 21 (1982) No. 8
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