BOOK REVIEWS means what some would call "pseudohalogen." The methods of forming B-X bonds are reviewed. Organosilicon chemistry is not included except where an organosilicon compound is a starting material. For enample, the "best method for making SiHsBr would appear to he through the reaction of excess HBr with CeHsSiHa a t -iX0C.," CsHsSiHa HBr = SiRJ3r CeHs. Rather more experiment,nl details are included in this chapter than are to he found in the other chapters. Chapter 8, Saline Hydrides, is written by Charles E. Messer, and consists of 22 pages. The chapter eomiders a t some length the obtaining and handling of high purity hydrogen gas as well as the hydride phases. Much detail on the preparation and handling of LiH, NsH, and CaHl follows. Adequate references are included to the other saline hydrides. Chapter 9, Sulfur-Nitn~gen-Fluorine Compounds, is written by Oskar Glemser, and consists of 10 pages. This chapter is unique in that it covers in considerable det,ail six specific substances, NSF, 8.NPs NSF*, N&F,, NIS~FI,and SINIF. . Chapter 10, Hypohditos and Compounds Containing the -OX Group, is written by Stanley hl. Williamson, and consists of 12 pages. A brief review of alkali metal hypohalites is followed by a somewhat more detailed account of the molecular hypohalites, such as, the oxygen fluorides and the hypofluorites of
+
+
~
A66
/
Journol of Chemical Education
strong acids, FON02, etc. Next, oxide hypofluorites are considered, such as C h O F and S h O F . Halagen(1) oxides, nitrates, fluorosulfonates, perchlarates, alkoxides, and csrboxylates concludes the chapter. I t is mv " minion that each author has been well-chosen to consider experimental details in his o m specialty. Furthermore, each has done a. very good job. While I cannot honestly see this volume taking its place as either textbook or lahoratory manual, I do feel that it will be an excellent place to which one can refer students for up-to-date, expert coverage of the ten topics.
.
S. YOUNG TYREE,JR. University o j h'orlh Carolina Chapel Hill Organometallic Chemistry
Eugene G. Rochow, Harvard Selected Topics in Modern Reinhold Publishing Corp., 1964. ix 112 pp. Figs. 13 X 18.5 cm. $1.95.
+
University. Chemistry. New York, and tables.
Organometallic compounds are not new, even though they have not been customarily mentioned in introductory courses. They have been known since the sc~eneeof chemistry developed out of alchemy, but the present century has witnessed a t,remendoua expansion in their number with attendant appheatians in medicine, biology, agriculture, the physics1 sciences, and the chemical industries. The branrlr of science now known as organometallic
chemistry was originated in the 1x30's byRobert Bunsen. This hook contains 104 pages of textual material in addition to a. complete index and a preface that is well worth reading. The first chapter is a n introduction in which the term organometollic is defined as applying only to those compounds in which organic groups are linked directly to metal atoms. Nomenclature is eonsidered here also. The second chapter deals with the nature of the carbon-metal bond. The structures of ionic and covalent arganometallic compounds are discussed, and the "sandwich" compounds such as ferrocene and hisbenzenechromium are described. The t,hird chapter deals with methods of preparation (usuall,~from snother orgmametallic compound); the Grignard reagent is discussed at some length in this connection. Typical reactions of orgmometallic compounds are described in the fourth chapter. The fifth chapter is devoted to Some Sigma-bonded Compounds, the sixt,h to Some Ionic Compounds, the seventh to Some Ddocalized-eleetronbonded Compounds, and the eighth to carbonyls. The student reader will probably be surprised by the many applications of organometallic compounds presented in the ninth chapt,er. This chapter contains 23 pages, which is more than twice the average length of the other chapters. Here the student will discover the chemical identit,y of suhst,ances wit,h m,hich he is (Conlinued on prior .4 6.9)
1
BOOK REVIEWS familiar, such as Mercurochrome and Merthiolate, and will read of the origins of chemotherapy in Ehrlioh's development of arsenieala. Other interesting applications of organometallic compounds diecueaed here include the use of tridkyltin compounds for permanent antisepsis of hoapital mattreaees, blankets, and pillows; the use of silicone stopcock grease, silicone oil for heating hatha, silicone protective oream for the hands, tetramethylsilane as an NMR standard, silicone elastomers in gaskets for high-altitude sircraft, and silicone polymers as waterrepellent 6hns and "abhesive" agents; and the use of tetraethyllead and tetramethylled as antiknock agents. The 6nal chapter is devoted to Literature Sonrcea. The author is to be commended for conceivinr that one of the ~m o s ~useful t h i n e he could du in a book of thia kind is tu head the reader toward the library. This little book written by an authority on the subject is another Reinhold paperback, intended to serve as a mpplement to any standard text in a general ohemistry course. After teachers have read it and have hsd their students read it, they may decide that parts of it could well supplant some of the material now found in textbooks. The textbook revolution has certainly not yet run its full course, and there can be little doubt that new texts and new editions will reflect the influence
..
A68
/
~~
~~
Journol of Chernicol Educotion
of the paperback supplements provided by thia and other series. LAWRENCE P. EBLIN Ohio Uniuwsity
Athens Advancer in Organorneiallic Chamisfry. Volume 1
Edited by F. G. A. St-, University of Bristol, England, and Robert Wmt, University of Wisconsin, Madison. xi 334 pp. Figs. and tables. 15.5 X 23.5 om. $11.
+
This hook is the first volume of a new annual series that adds to the growing collected literature of orgrtnometallic chemistry. Prior to this date review articles dealing with this area of chemistry were scattered throughout the journal and hard-cover review litersture. Reviews dealing with organometallic chemistry were found in bath inorganic and organic review series and in even more speoialiaed review volumes. An attempt to collect a t least most of them in one place is a service to those active in the field. One may, however, question whether the present series is the best way of accomplishing this purpose. A hard cover multi-author volume of this type has two major drawbacks: first of all, it is rather expensive (the price of volume 2 is already up to $15!); secondly, one is forced to buy a t least several articles which are of no or of littleinterest to him along with the one or two which he really wants in his files.
The many review series which the various publishers, with their eyes on the continually growing captive market of technical libraries, have seen fit to launch have resulted already in much wasteful duplication of effort. This new series, even in its first volume, has examples of this. Thus, the excellent article by H. C. Clark on Perfluoroalkyl Derivatives of the ElemenLq in "Advances in Fluorine Chemistry, Volume 3" (1963) is duplicated by fully one half of "Fluorocsrbon Derive tives of the Metals" (which also is an excellent summary), by P. M. Treichel and F. G. A. Stone in this volume. This is especially to be deplored since Aoademic Press, which is especially notorious for its " series, "Advances in publishes both the Organometallic and Fluorine Chemistry series. Less serious but still apparent is the overlap between Infrared and Raman Spectral Studies of r Complexes Formed between Met& and Rings by H. P. Fritz (this volume) and Use of Infrared and Raman Spectroscopy in the Study of Organometallic Compounds by H. D. Kaesz in "Progress in Solid State Chemistry, Volume 1." The present volume also contains an excellent article on Diene-Iron Carbonyl Complexes and Related Species (R. Pettit and G. F. Emerson), a useful summary of Reactions of Organotiu Hydrides (H. G. Kuivila), and &o summaries of the more or less personal researches in rather narrow fields by H. Gilman (Organic Substituted Cyclosilrtnes, with G. L. Schwebke) and R. Fuson (Conjugate (Catinued a page A70)
