Organosilicon and Bioorganosilicon Chemistry - ACS Publications

book reflects Vogel's individual taste which is even demonstrated by such intriguing subheadings of the introductory chapter as. “Stable Carbocation...
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Book Reviews ticularly interesting is the discussion of carbocations and organometallic complexes, bringing together interesting aspects of transition-metal complexes and their carbocation analogues. The concluding chapter discusses carbocations in synthesis, rounding out the number of significant topics condensed in a book of 600 pages. Obviously such a broad scope coverage cannot be all encompassing, and the author made his own choices of preference. This is, however, not detracting from the value of his book. The book reflects Vogel’s individual taste which is even demonstrated by such intriguing subheadings of the introductory chapter as “Stable Carbocations and Red Wine” followed by “The Aging of Red Wine and Transient Carbocations” leading to the more trivial “Gibbs Energy Diagrams”. I frequently wondered how to catch my students’ early interest for carbocations and to condense a very large and complex field into manageable proportion. I must say to have learned much on all counts from Vogel’s book. The only negative note on this highly recommended book, well suited for advanced students and researchers alike, is its prohibitive price. It will regretfully limit its availability to libraries and even so to only the better endowed ones. George A. Olah, University of Southern California

Dictionary of Organometallic Compounds. J. Buckingham, executive editor. Chapman and Hall, London, New York, and Toronto. 1984. 3232 pages (in three volumes). $990. As stated in the preface, “the aim of this publication is to review the whole field of organometallic chemistry, to select those compounds which are in the opinion of the specialist Editors most typical, representative, interesting, and useful or potentially useful, and to present their properties and selected bibliography in an orderly and systematically indexed fashion.” The work is organized into three volumes, two of which contain compounds of all elements except the halogens, noble gases, unstable radioactive elements, H, C, N, 0, P, S, Se, and Te listed alphabetically according to the element; Volume 1contains Ag-Mn and Volume 2, Mo-Zr. At the beginning of the section on each element is up to one page of useful information for quick reference concerning physical properties, availability, handling, toxicity, isotope abundance, spectroscopy, analysis, types of compounds covered, and references to books and reviews. Approximately 15000 entries are found in these two volumes, all the way from one for Bk to 2222 for Fe. They are listed according to the molecular formula starting with C and H and proceeding with other elements in alphabetical order. Counterions of cationic or anionic entries are not part of the molecular formula. At the beginning of each section is a compilation of structural formulas for each entry, as far as the structures are known. The compilation is extremely useful for quick, visual searching. Each compound is listed by empirical formula, one or more names, and a CAS registry number. The compound’s physical properties are then described to the extent that they are known, and any hazards or toxicity noted. The compound’s use or importance (first of its kind etc.) is sometimes noted, although this practice is dependent upon the knowledge and dedication of the author for the section on that element. Each entry concludes with references and points out what can be found in each (preparation, X-ray structure, IR, NMR, etc.). One negative feature is that the referencing is sometimes sloppy. For example, the first report is sometimes omitted in favor of a later, usually more complete, report by a different author; both should be included. Et al. is also misused; papers by two authors, A and B, are listed as being written by “A, et al.”, and in a t least one case, even more annoyingly, the same paper is referenced several times as being “B, et al.”. Surprisingly, however, I found few names misspelled or wrong initials used. The third volume contains a name index, a molecular formula index, and a CAS registry number index. The name index is of limited use since many compounds can be named in several ways. For example, a “trineopentyl” zirconium complex is listed, but Ta(CH-t-Bu)(CH,-t-Bu)3 is listed only as “tris(neopenty1)neopentylidene/tantalum”. There is the occasional gaffe; for example, [W(C-t-Bu)Cl,]- is listed as “tetrachloro(1,l-dimethylpropylidyne)tungsten(l-)”, instead of 2,2-dimethylpropylidyne. I found the molecular formula index to be more useful. One way in which the dictionary could be improved is to note which compounds have analogues containing another metal. For

Organometallics, Vol. 5, No. 3, 1986 607 example, Mo(CO)&CPh2)is known for M = Cr, Mo, and W. Each compound is listed in the appropriate section (apparently care was taken to list all compounds in this case and in several other cases that I spot-checked) but each listing did not note that analogues containing two other metals are known. The additional space required to do so would be minimal. One of the main weaknesses of the dictionary is inherent in a work of this type, and that is that selections are a t times somewhat subjective and/or random. One of the main strengths is that one can get an idea quickly as to how much work has been done on a given element and what are some of the major types of compounds available. Since references to other sources are included, the dictionary can be a good place to start. The dictionary will be most useful to those who have little knowledge of other sources, or those, knowledgeable or not, who are well-heeled enough to afford to have their own copy a t their fingertips. It certainly should be a required reference for any library. Richard R. Schrock Massachusetts Institute of Technology

New Frontiers in Organometallic and Inorganic Chemistry. Edited by Y. Huang, A. Yamamoto, and B.-K. Teo. Science Press, Beijing. Published in the USA by S.P. Richards Publ., New Providence, NJ. 1984. xxix + 527 pages. $59.50. This book brings the 39 plenary lectures and the 49 posters presented at the Second China-Japan-USA Trilateral Seminar on Organometallic and Inorganic Chemistry in Shanghai in June 1982. Most of the Japanese and American work reported here will have been published in the meantime (if it had not been published already before the meeting took place), so it is the Chinese work which will be of main interest to the reader. Reports of Chinese research in areas of current interest and fashion show that they are working hard to catch up after their difficult years. Lectures or posters on, for instance, cluster chemistry, organolanthanide compounds, transition-metal-catalyzed polymerization, metalloporphyrins, iron-sulfur complexes, arsenic ylides, organic compounds of early transition metals, and organosilicon chemistry are found among the Chinese contributions in the book. The names of the Chinese authors for the most part will not be familiar to most readers of this journal, but no doubt this will change in the future since research activity in chemistry in the People’s Republic of China is increasing steadily. This is not a book that individuals will want to purchase, but it is one that chemical libraries might want to have. Dietmar Seyferth, Massachusetts Institute of Technology

Organosilicon and Bioorganosilicon Chemistry: Structure, Bonding, Reactivity and Synthetic Application. Edited by H. Sakurai. Ellis Horwood Ltd, Chichester, and Halsted Press (Wiley), New York. 1985. 298 pp. $46.95. The present book brings the 27 Plenary and Invited Section Lectures presented at the Seventh International Symposium on Organosilicon Chemistry which was held in Kyoto in September 1984. The title of the book is misleading: only one of the 27 papers (that by R. Tacke) deals with bioorganosilicon chemistry. The subject matter of the other 26 papers is heavily slanted toward the currently popular research areas of organosilicon chemistry: compounds with multiple bonds involving silicon, reactive silicon-containing intermediates, and organosilicon compounds in organic synthesis. Among the authors are the expected names, well-known to those who follow organosilicon chemistry: West, Brook, Wiberg, Bock, Davidson, Gaspar, Weber, Watanabe and Nagai, Gusel’nikov, Eaborn, Corriu, DunoguBs, Liu, Fleming, Tamao, and Lukevics. Several interesting papers that do not involve the abovementioned areas of currently fashionable and popular organosilicon research are worth noting: mechanistic studies of the new group-transfer polymerization procedure, which involves silyl ketene acetals as reagents, by Sogah and Farnham of Du Pont; the synthesis of sila drugs and microbial transformations of organosilicon compounds, by R. Tacke; the conversion of some polyorganosilicon precursors to ceramics, by R. H. Baney and co-workers at Dow Corning. Also of interest to your reviewer was Tadashi Wada’s account of past and current trends in the silicon

608 Organometallics, Vol. 5, No. 3, 1986 industry in Japan. His section on “Future Prospects for Silicones” suggests that (0rgano)silicon research will have a healthy and growing industrial base in the years to come. It is sometimes interesting (and sometimes amusing) to read the acknowledgments a t the end of papers. One in this book merits mention. Invitations to speak at a conference such as this one usually are issued far in advance. Not just a few of us, having accepted an invitation to speak at some such conference or other months in advance, have “sweated” those months trying to get together enough new results to give a reasonable talk when the time comes. Usually, we do not start from scratch but plan to talk about an ongoing, albeit only partly developed area of research. Not so Hans Bock, who has been noted for his interesting research a t the forefront of many different areas of chemistry. His acknowledgment reads: “Thanks are expressed especially to the co-workers mentioned, who-presently working in other areas of main-group chemistry-on short notice switched to organosilicon chemistry and produced in less than half a year the results reported here.” This book will be of interest to organosilicon aficionados as well as those “outsiders” who would like to find out something about the current directions of organosilicon research. Although it consists of camera-ready manuscripts, this book has been attractively produced. Dietmar Seyferth, Massachusetts Institute of Technology

Gmelin Handbook of Inorganic Chemistry. 8th Edition. Sn, Organotin Compounds. Part 11. Trimethyltin- and Triethyltin-Oxygen Compounds. H. Schumann and I. Schumann, volume authors. U. Kruerke, volume editor. Gmelin Institut fur Anorganische Chemie der Max-Planck-Gesellschaft zur Forderung der Wissenschaften and Springer Verlag, Berlin/Heidelberg/New York. 1984. x + 292 pages. DM 995. In this, the eleventh volume of the Gmelin organotin series, the Schumanns begin their coverage of organotin compounds

Book Reviews containing Sn-0 bonds. This, if one includes the patent literature, is a vast subject. The present book deals only with mononuclear trimethyl- and triethyltin-oxygen compounds. These include the hydroxides (but not the dinuclear oxides), the alkoxides, carboxylates, peroxides, carbamates, and various derivatives of inorganic oxyacids. Because trimethyl- and triethyltin derivatives are so very toxic, their applications are restricted and, as a result, this book is not overly long. Information concerning preparation, physical properties, structure, spectroscopic properties (IR, ‘H, I3C,Il9Sn NMR, llgmSnMossbauer, PE), chemical reactivity, and biological activity is given, if available, for the compounds covered, in text and in tables. Figures show those structures which have been determined. The literature cutoff date is December 31,1982. A useful feature in this book is the up-dating of the coverage of the general review literature of organotin compounds (earlier collections of reviews are found in Vol. 1, 5, 7 , 8, and 9 of the organotin series). A fine net was used in chasing down this review literature, and some strange fish were caught. For instance, in this book, in the section of reviews on analysis (page 2), the review on “Harmful Substances in Women’s Underwear” (in Japanese) will be one of particular interest to all organotin chemists. Perhaps more useful to the user of this book is the 36-page list of general literature on organotin-oxygen compounds which includes general reviews and also articles on preparation and reactions, physical properties, analysis, toxicology and biological applications, and uses (including a list of patents). We may assume that the literature coverage, as usual, is very thorough and that littl has been missed. The 96 cited references on (CH3),SnOH, for instance, range from the very old [Cahours, A. Justus Liebigs Ann. Chem. 1860,114,3541 to the recent (but sometimes hard to track down) [e.g., Kyu Lee, I.; Bae, B.-S.; Ghim, G.-J. Taehan Hwahakhoe Chi 1980,24,393] and include chemical, physical, and biological journals. This is a useful addition to the Gmelin organotin series. Further volumes will deal with other R,Sn-oxygen compounds and the much more numerous RzSn and RSn types. Dietmar Seyferth, Massachusetts Institute of Technology