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The chemistry of functional groups. the chemistry of ketenes, allenes, and related compounds, parts 1 and 2
314
Vol. 4, edited by A. Padwa, Marcel Dekker, New York, 1979, pp_ xii + 343, price SFr. 82.00.
Organic Photochemistry,
This volume follows the three earlier volumes edited by Orville Chapman but no change in the successful editorial policy is implied according to the preface to Vol. 4. Four areas of organic photochemistry have been chosen for the separate chapters. The topics are alkenes in solution (142 pp.), nonconjugated aryl olefins (47 pp.), cyclopropanes (70 pp.), and cyclopropene derivatives (66 pp.). Detai!ed references occur at the end of each chapter. The first chapter by P. J. Kropp will have the most general appeal to readers. It describes the possible excited singlet and triplet states of alkenes and then discusses the observed photochemical behaviour of both acyclic and cyclic alkenes in terms of the excited states. Triplet behaviour is the simpler because there is only one low lying excited state. Thus, sensitised irradiation usually produces one type of reaction depending on the structure of the olefin and the reaction conditions. In contrast, there are two or three low lying excited singlet states in close proximity so that several photochemical processes may compete. The rather special copper(I)-catalysed photoadditions are also noted. The chapter concludes with an account of styrenes. To help the experimentalist, some practical tips are included. The coverage is up to the end of 1978. The other, shorter, chapters by H. Morrison, S. S. Hixson, and A. Padwa, respectively, will be of particular use to workers in these more specialised fields. The book ends with author and subject indexes. Each chapter is a very good account of the current knowledge in its field and should prove to be a good entry point for understanding each of these now rather complex areas of organic photochemistry. C. J. T.
The Chemistry of Functional Groups. The Chemistry of Ketenes, Allenes, and Related Compounds, Parts 1 and 2, edited by S. Patai, Part 1: pp. xiv f 485,
Part 2: pp. xiv + 497, John Wiley/Interscience,
1980, price g35 (each Vol.).
In this new addition to Patai’s inimitable series on organic functional groups the subject matter is presented in 20 chapters by different and mainly American authors. Although ketenes and allenes were in fact discussed in the first volume of this series (the Chemistry of Alkenes) the growth of the subject in the past fifteen years and its importance fully justify a renewed and more extensive treatment. Organic chemists familiar with any of the previous volumes will feel at home with the general plan of the books, namely an introductory chapter treating general and theoretical aspects of the group
315
under discussion followed by other chapters dealing with its formation, characterisation, reactions, and special aspects. In some chapters allenes and ketenes are treated side by side, others are reserved exclusively for one group only. For instance, Chapter 7 (R. S. Ward) describes the preparation of ketenes while Chapter 8 (W. T. Brady) deals with the synthetic uses of ketenes and allenes. In addition to the expected headings unusual aspects have not been neglected. Thus we find chapters on the “Electrochemistry of allenes and cumulenes” (D. G. Peters, W. F. Carroll Jr., D. M. La Perriere and B. C. Willett), and on the “Biological formation and reactions” (C. H. Robinson and D. F. Covey) dealing with naturally occurring allenes and enzymatically generated allenes and ketenes. The coverage of ketenes and its important derivatives (ketene 0,0-acetals, thioacetals, imines and methyleneketenes) as well as that of allenes is very comprehensive_ The preparation of allenes for instance (Chap. 20, H. Hopf) is particularly informative, containing nearly 1000 references! Citation from the literature is uniformly good up to the mid-seventies for all chapters with a few authors including references up to 1978. As so often happens with multi-author books several chapters, unfortunately very important ones, did not materialise. These were “The Photochemistry of Ketenes and Cumulenes”, “ Cycloadditions Involving Ketenes and Cumulenes” and “Rearrangements Involving Ketenes”. However, we are promised that these omissions will be rectified in a future supplementary volume_ The regrettable gaps caused by these non-deliveries is slightly narrowed since some of these topics are perfunctorily treated in other chapters. Another, though not serious shortcoming, is the vagueness implied by the second half of the title: ‘%nd reIated compounds”. It would have been useful to the reader to learn at least in the “Foreword”
which other cumulenes
(apart from ketenes and allenes) are included in the discussion. Only a perusal of the list of contents and of the introduction to each chapter will reveal what other “related compounds” are treated. The only heterocumulene to which a full and informative chapter is devoted are the “Carbodiimides” (Y. Wolman). Other heterocumulenes are either not discussed at all (e.g. Chapter 20) or given only incidental treatment. As always the book production is of the high standard expected from this series, with clear and easy-to-follow diagrams which make browsing through the chapters a stimulating and pleasurable exercise. Any library that has to cater for organic chemists must regard this new addition to the Patai reference library as an essential acquisition. H. S.
Vol. 4, edited by A. Padwa, Marcel Dekker, New York, 1979, pp_ xii + 343, price SFr. 82.00.
Organic Photochemistry,
This volume follows the three earlier volumes edited by Orville Chapman but no change in the successful editorial policy is implied according to the preface to Vol. 4. Four areas of organic photochemistry have been chosen for the separate chapters. The topics are alkenes in solution (142 pp.), nonconjugated aryl olefins (47 pp.), cyclopropanes (70 pp.), and cyclopropene derivatives (66 pp.). Detai!ed references occur at the end of each chapter. The first chapter by P. J. Kropp will have the most general appeal to readers. It describes the possible excited singlet and triplet states of alkenes and then discusses the observed photochemical behaviour of both acyclic and cyclic alkenes in terms of the excited states. Triplet behaviour is the simpler because there is only one low lying excited state. Thus, sensitised irradiation usually produces one type of reaction depending on the structure of the olefin and the reaction conditions. In contrast, there are two or three low lying excited singlet states in close proximity so that several photochemical processes may compete. The rather special copper(I)-catalysed photoadditions are also noted. The chapter concludes with an account of styrenes. To help the experimentalist, some practical tips are included. The coverage is up to the end of 1978. The other, shorter, chapters by H. Morrison, S. S. Hixson, and A. Padwa, respectively, will be of particular use to workers in these more specialised fields. The book ends with author and subject indexes. Each chapter is a very good account of the current knowledge in its field and should prove to be a good entry point for understanding each of these now rather complex areas of organic photochemistry. C. J. T.
The Chemistry of Functional Groups. The Chemistry of Ketenes, Allenes, and Related Compounds, Parts 1 and 2, edited by S. Patai, Part 1: pp. xiv f 485,
Part 2: pp. xiv + 497, John Wiley/Interscience,
1980, price g35 (each Vol.).
In this new addition to Patai’s inimitable series on organic functional groups the subject matter is presented in 20 chapters by different and mainly American authors. Although ketenes and allenes were in fact discussed in the first volume of this series (the Chemistry of Alkenes) the growth of the subject in the past fifteen years and its importance fully justify a renewed and more extensive treatment. Organic chemists familiar with any of the previous volumes will feel at home with the general plan of the books, namely an introductory chapter treating general and theoretical aspects of the group
315
under discussion followed by other chapters dealing with its formation, characterisation, reactions, and special aspects. In some chapters allenes and ketenes are treated side by side, others are reserved exclusively for one group only. For instance, Chapter 7 (R. S. Ward) describes the preparation of ketenes while Chapter 8 (W. T. Brady) deals with the synthetic uses of ketenes and allenes. In addition to the expected headings unusual aspects have not been neglected. Thus we find chapters on the “Electrochemistry of allenes and cumulenes” (D. G. Peters, W. F. Carroll Jr., D. M. La Perriere and B. C. Willett), and on the “Biological formation and reactions” (C. H. Robinson and D. F. Covey) dealing with naturally occurring allenes and enzymatically generated allenes and ketenes. The coverage of ketenes and its important derivatives (ketene 0,0-acetals, thioacetals, imines and methyleneketenes) as well as that of allenes is very comprehensive_ The preparation of allenes for instance (Chap. 20, H. Hopf) is particularly informative, containing nearly 1000 references! Citation from the literature is uniformly good up to the mid-seventies for all chapters with a few authors including references up to 1978. As so often happens with multi-author books several chapters, unfortunately very important ones, did not materialise. These were “The Photochemistry of Ketenes and Cumulenes”, “ Cycloadditions Involving Ketenes and Cumulenes” and “Rearrangements Involving Ketenes”. However, we are promised that these omissions will be rectified in a future supplementary volume_ The regrettable gaps caused by these non-deliveries is slightly narrowed since some of these topics are perfunctorily treated in other chapters. Another, though not serious shortcoming, is the vagueness implied by the second half of the title: ‘%nd reIated compounds”. It would have been useful to the reader to learn at least in the “Foreword”
which other cumulenes
(apart from ketenes and allenes) are included in the discussion. Only a perusal of the list of contents and of the introduction to each chapter will reveal what other “related compounds” are treated. The only heterocumulene to which a full and informative chapter is devoted are the “Carbodiimides” (Y. Wolman). Other heterocumulenes are either not discussed at all (e.g. Chapter 20) or given only incidental treatment. As always the book production is of the high standard expected from this series, with clear and easy-to-follow diagrams which make browsing through the chapters a stimulating and pleasurable exercise. Any library that has to cater for organic chemists must regard this new addition to the Patai reference library as an essential acquisition. H. S.