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Book Review: The Organic Chemistry of Phosphorus. By A. J. Kirby and S. G. Warren. Monograph 5 of the series “Reaction Mechanisms in Organic Chemistry”. Edited by C. Eaborn and N. B. Chapman

✍ Scribed by L. Horner


Publisher
John Wiley and Sons
Year
1968
Tongue
English
Weight
164 KB
Volume
7
Category
Article
ISSN
0044-8249

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✦ Synopsis


up to about 1965/1966. Its publication will be welcomed by all who wish to learn about this field of organic chemistry, and it should be included at least in the libraries of all universities and colleges.

W. Tochterrnann [NB 738 IE] The Organic Chemistry of Phosphorus. By A. J . Kirby and S . G. Warren. Monograph 5 of the series "Reaction Mechanisms in Organic Chemistry". Edited by C. Euborn and N . B. Chapman. Elsevier Publishing Company. Amsterdam-London-New York 1967. 1st Edit., xi, 4U4 p ~. , 4 figures, 21 tables, Dfl. 65.-. A great deal of expert knowledge and courage are required to present a monograph on such an extensive topic. However, it is pointed out in the preface that certain mechanistic principles are to be laid down to familiarize the newcomer with the specific problems of organophosphorus chemistry. The authors see the absence of quantitative data in the original papers as one of the limits of their commentary. The experienced reader very soon finds that the discussion of fields that have already been well covered in other monographs (cf. R . F. Hudson: Structure and Mechanism in Organophosphorus Chemistry), or that are particularly familiar to the authors from their own experience is of a high scientific standard. This is true of Chapter 1: Electronic Structure; Chapter 2: Structure and Reactivity; Chapter 3: Nucleophilic Attack of Compounds of Trivalent Phosphorus; Chapter 4: Elimination of Compounds of Trivalent Phosphorus; Chapter 5 : Free-Radical Reactions on Phosphorus; Chapter 7: Reactions that d o not occur on the Central P Atom; Chapter 8: Nucleophilic Attack on Compounds of Tricoordinated Phosphorus; Chapter 10: Nucleophilic Attack on Compounds of Tetrahedral Phosphorus(v), and Chapter 11 :

Phosphorylation. The last two chapters are particularly impressive for their completeness. On the other hand, Chapter 6: Four-Center Rearrangements, and to a lesser degree Chapter 9: Nucleophilic Attack on Phosphonium Salts and Compounds of Pentacovalent Phosphorus, seem rather stunted. Chapter 6 deals almost exclusively with olefination via phosphonium ylides, with n o regard for historical relationships. More recent developments such as PO-activated olefinations are by-passed with references, and their importance in syntheses is not mentioned. N o reference is made to later variants by Zimmer, Corey, Machleidt, and Bergelson. This chapter also contains many inaccuracies and errors, which should be eliminated for the second edition. The well-informed reader also notices the absence of references to important review articles, particu-


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