book reviews Organomelalllcs In Organlc Synlhesls
J. M. S u m and D. St. C Black, Monash University. Chapman Hall Ltd., London, 1974. vii 147 pp. Figs. and tables. 16.5 x 21 cm. Text addition. $7.25.
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This is a new introductory textbook where textbooks are scarce and good ones rarer still. The history of the chemistry of organometallic compounds stretches back considerably farther than that of other areas of chemistry. It probably began in the early 19th century with the first report of Zeise's salt. However, during the past two decades since the discovery of the new sandwich type transition-metal r-complex of organornetellie compounds, ferracene, in 1952, the chemistry of organometallic compounds has made remarkable progress. Major fields in the development of this chemistry include synthesis of a large nnmber of organometallic compounds with their structure elucidations and the theory on the nature of their bonding, their reactions and reactivities, and the application of these compounds as catalysts for industrial homogeneous processes. These industrial processes include Ziegler-Natta olefin polymerization, hydroformulation of olefins (Oxo-~rocess),hydrogenation, isomerization of olefins, and oxidation of ethylene t o acetaldehyde (Wacker process). Needless to say, organic chemists have made consistent efforts t o use organametellic compounds for organic synthesis as intermediates or catalysts since 1952 because of their unique reactivities. The advancement of this area has been aecelerated hv,the creation of new effective svnthetIC methods and reagents. l'hr application of orgsnon~etnlliecompounds for synthesis has spread over a bnud aren or' modern urganic chemistry and has greatly cantributed t o its rapid progress. There are a number of review articles, chapters and books, on specific reagents or on the soecial reactions usine.. soecific or. ganometnllic compounds: however. there has been no adequate buok trrntlng the applicatim of orgnnometsllic rompounds lur organic synthesis. Some books an the ~
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chemistry of organometallic compounds have attempted t o compile the information in this area and to classifv , resoective svnthetic reacciow and methods wrthout much success because o i the difficulties in revering and summarizing such a n extensive body of information. The authors introduce their subject with the following concise statements: "This is a hook about organic chemistry, especially the synthesis of organic compounds. However, we are not concerned with the whole field of synthesis but rather with those reactions where the starting material or an intermediate is a substance having a carbon-carbon bond." They also make the effective opening remarks: "We believe that i t is now timely to present a concise aecount of the applications of organometellics starting materials, intermediates, and catalysts in and generality, and in the nature of the particular atoms being linked together in the synthetic processes." Part one deals with a brief introduction of the historical background of chemistry of organometallic compounds, the versatility of organometallic compounds and the different roles that metal atoms can play in organometallie reactions. A classification of reaction types based on mechanism is introduced. Part I1 and I11 deal systematically with organometallie processes for the construction of different classes of chemical bonds. Such bond formation generally involves the carbon atom attached directly t o the metal atom of the organometallic starting material, and the reactions to be discussed are grouped according t o the type of bond being formed, sueh as earboncarbon, earbon-hydrogen, carbon-nitrogen, and so on. Part I1 deals with construction and modification of csrbon-carbon bonds, including double and triple bonds, by such diverse processes as the alkylation and acylation of carbanions (Chapter 3), the isomerization and oligomerization of alkenes and alkynes (Chapter 41, and by carbon monoxide insertion (group migration) reactions (Chapter 5). Part 111 deals with organometallic methods for joining carbon atoms t o elements other than carbon, such as hydrogen (Chapter 61, or nitrogen, phos~
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. . . A483 . . . A482 K A Johnsruno. Mass Spectrometry for Organi~.Chem~sr5 .\'orrnnn I. l I ' m n h . q rd~tor.Terhnqucof Elwtrouryantc Synthesis Volume V, Part 1 Ashok K. Vijh, The Electrochemistry of Metals and Semieonduetors Charles K. Mnnn. Thomas J , Vickers, and Wilson M . Guliek, Basic Concepts in ~ldetronieInstrumentation W . L. Jol1.v. editor, Metsl-Ammonia Solutions A. H.Cowley, editor, Compounds Containing Phosphorus-Phosphorus Bonds R. G. Pearson, editor, Hard and Soft Acids and Bases Wallace S. Broecker, Chemical Oceanography C. E. Klopfenstein and C. Wilkins, editors, Computers in Chemical and Biochemical Research, Volume 2 P. G. de Gennes, The Physics of Liquid Crystals William 0. McCogg, Jr., Jewish Nobles and Geniuses in Modern Hungary Michael Faradoy, Chemical Manipulation New Volumes in Continuing Series
J M. S u m , and I ) S r C i7lock. Organometallics in Organic Synthesis
phorus, oxygen, sulfur, and halogen atoms (Chapter 7). Throughout, emphasis is placed on hond-making and bond-breaking, and the role of the metal atom in these processes. The book treats the subject matter comprehensively and concisely. The authors are commerided for their competent and logical classification of the vast information. This book is well written and errors are scarce. This book is recommended for senior students or even for first year graduate students as a textbook or a supplementary textbook depending upon the nature of the class. As the major theme of this book is the synthesis of organic molecules, the preparations and properties of organometallie compounds as such are not emphasized. The author said that these details are readily available from a variety of other books and reviews, but i t is worth mentioning that organometallic reagents are often highly reactive, invariably toxic, and should be handled with care. The reviewer strongly feels that this book should list major book and review articles dealing with such relevant subjects as organometallic compounds, handling airsensitive compounds, and characterization of organometallie compounds. Many of the 134 references cited a t the end of the book are not really representative. A well chosen list of g w d references and reading material is important to this type of book.
Mass Spectrometry for Organlc Chemlsts
R. A. Johnstone, University of Liverpool. Cambridge University Press, 1972. $14.95. Mass spectrometry hm berome surh an important technique in strurlural a n n l ~ i s that it can no longer be ignored in the undergraduate chemistry curriculum. However, the mass spectra of many organic compounds contain sueh a large amount of information that the beginner's task is especially difficult. This makes an introductory text, which reflects the rapid advances of the last decade, welcome. "Mass Spectrometry for Organic Chemists" introduces the subject in a clear, pragmatic, and straightforward style. Its reader can gain an appreciation of the utility, as well as the limitations. of mass soectrometric technrque5. Unfortunately, the practical skill of interpreting mass spectra in order t o determine structures of organic molecules can not he achieved using this book. Althouch the author emphasizes the value of ape-rience in applying mass spectrometry to structural problems in organic chemistry, he provides little opportunity t o develop a working knowledge of isotopic abundance8 and ion-fragmentation patterns. There are no problem sets through which experience could be gained and the examples of analyzed spectra of "unknowns" are not adequate. Continued on page A484 Volume 52, Number 10, October 1975 / A483
