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Book Review Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis. Edited by J. G. Verkade and L. D. Quin

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Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis. Edited by J . G. Verkade and L. D. Quin. VCH Verlagsgesellschaft, Weinheim/VCH Publishers, Deerfield
Beach 1987. xvi, 717 pp., hard cover, DM 258.00.--ISBN
In “P-3 1 N M R Spectroscopy in Stereochemical Analysis,” John Verkade and Louis Quin have provided a thorough coverage of the field involving organophosphorus
compounds and phosphorus-metal complexes. The 20
chapters and over 700 pages written by experts in the field
cover nearly all aspects of 3’P-NMR spectroscopy. A discussion of ’ P chemical shifts and their interpretation is
presented in the first two chapters. A useful “nuts and
bolts” approach to obtaining 3’P N M R spectra is provided
by J . C . Tebby in Chapter 1. A short compilation of representative ” P chemical shifts is also provided. E. Huck and
G. Heckmann discuss empirical methods for interpreting
” P chemical shifts, largely of compounds with P-heteroatom multiple bonds. These compounds have not often
been included in recent reviews of ” P chemical shifts.
Chapters 3-6 discuss more detailed theoretical and experimental aspects, including one- and two-dimensional multiple pulse experiments. 31P N M R of oriented phases and
theoretical analysis of 3’P chemical shifts and coupling
constants complete the first section. Both the chapter by C.
B. Chesnut on ” P chemical shifts and that by D. J. Jameson on coupling constants spend considerable time on basic theory. In fact in the later, most of the discussion is
directed towards a generalized analysis of coupling between first- and second-row elements, with a minor emphasis on phosphorus.
Chapters 7-10 provide specific applications of the use of
3 ’ P chemical shifts in solving structural, conformational,
and mechanistic aspects of phosphorus chemistry. The importance of the stereospecificity of 3 1 P coupling constants
to all the NMR-active elements is described in Chapters
11-13. The remainder of the book is devoted to stereochemical aspects of metal-phosphorus compounds.
Considering that two other 31P NMR books have recently appeared (D. G. Gorenstein (ed.): P-31 NMR: Principles and Applications, Academic Press, New York 1984; C.
Tyler Burt: Phosphorus NMR in Biology, C R C Press, Boca
Raton, FL, USA 1987) and that the Verkade and Quin
book costs $125, is another book on ” P N M R needed?
The answer is a definite yes. The authors have done a really commendable j o b in minimizing the overlap between
the three recent 3’PNMR books. The 1984 and 1987 (Tyler)
books largely have emphasized theory and applications to
biological phosphorus studies and the book by Verkade
and Quin has emphasized organophosphorus and phosphorus-metal complexes. They have provided a highly
readable book that researchers in the field will find very
useful. It was once possible to largely cover the field of
phosphorus N M R in the single volume by John Van Wazer. All of the more recent ,books are needed to adequately
cover this enormous field and still have been highly selective in the material they could cover.
There are a few minor typos (McFarlane’s equation for
line width at half height and a missing third 90” pulse in
the NOESY sequence, for example) and a few minor questionable statements (Gallagher’s comment about the concentration effect (?) on 0 - 1 8 isotope shifts on p. 322), but
otherwise the book is very well written. The one unfortunate consequence of putting together such a massive undertaking is the time it must have taken for the book to be
published. Many of the chapters have references only to
Angew. Chem In,. Ed Engl. 2711988)
No. 4
1984 and some even earlier. These are only minor concerns, however, and overall John Verkade and Louis Quin
and the publisher should be commended for putting together a fine volume.
David G. Gorenstein [NB 881 IE]
Chemistry Department, Purdue University
West Lafayette, I N 47907 (USA)
Diazo Compounds. Properties and Synthesis. By M . Regitz
and G. Maas. Academic Press, New York 1986. xvi, 596
pp., bound, $ 125.00.-ISBN 0-12-585840-X
In addition to their importance as a starting point for
preparing carbenes ( G . Maas, Transition-metal Catalyzed
Decomposition of Aliphatic Diazo Compounds-New Results and Application in Organic Synthesis, Top. Curr.
Chem. 137 (1987) 75), diazoalkanes are useful building
blocks for cycloadditions ( M . Regitz and H . Heydt: “Diazoalkanes” in S . Patai (Ed.): 1,3-Dipolar Cycloaddition
Chemistry, Vol. 1, p. 393, Wiley, New York 1984). Since
diazo compounds are so useful in synthesis, everyone who
works with them must have felt the lack of a n updated account of developments in this area. The comprehensive
treatment in the book reviewed here now satisfies this
long-standing need. The authors, who have many years of
practical experience in this field, intend the treatment to be
suitable for final year degree students and preparative
chemists in universities and industry.
The book consists of two parts. Part I, “Properties of Aliphatic Diazo Compounds”, contains four chapters (structure and spectroscopic properties, thermal properties, reactivity towards acids, and photochemistry). Part 11, “Syntheses of Aliphatic Diazo Compounds”, has twelve chapters, covering methods which include the diazotization of
amines, the Forster reaction, the dehydrogenation of hydrazones, the Bamford-Stevens reaction, the cleavage of Nalkyl-N-nitroso compounds, the transfer of diazo groups,
and substitution reactions of diazoalkanes and isotopically
labeled diazo compounds. The reader benefits greatly from
the orderly arrangement of the material, and from the carefully prepared formula schemes which can be taken in at a
glance, and are in many cases supported by comprehensive
tables and bibliography.
The tightly-knit, factual style is pleasing. However, the
treatment of the Forster reaction in Chapter 6 is too brief,
and on pages 221,222, and 226 we find three different mechanistic versions of this reaction directly adjacent to each
other without any additional discussion. Similarly, virtually no mechanistic interpretation is given for the introduction of diazo groups using the nitroso reaction (Chapter 7).
The book is a mine of information for the specialist, not
least because of the literature references, of which there
are more than 1800, covering the period u p to the end of
1982. The incomprehensibly long delay in the appearance
of the book-for which the publishers are no doubt chiefly
responsible-has been bridged by the authors’ inclusion of
a n addendum, which is, however, very condensed (it contains no structural formulas!), and therefore makes difficult reading. It contains 184 literature references, for the
period u p to and including January 1986.
The layout of the monograph is attractive. The text contains scarcely any printing errors. The same is not quite so
true of the structural formulas and tables, but this hardly
detracts from the excellent overall impression left by this
first edition of the work.
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spectroscopy, nmr, book, quinn, edited, analysis, stereochemical, verkade, review, phosphorus
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