Organotin compounds have many applications in indus-try, the largest being as PVC stabilizers. This book isconcerned with the uses of tributyltin derivatives over thepast 30 years as paint additives, where they function asantifouling agents for the protection of marine andfreshwater ships from organisms such as barnacles, tubeworms and seaweeds, which otherwise increase thefrictional resistance of the underwater parts of vessels. Theorganotin may be in the form of (Bu3Sn)2O or, moreeffectively, Bu3SnO– groups bonded to a polymer chain.The discovery that very low concentrations of Bu3Sn–(nanograms per litre) are also toxic to molluscs such asoysters and mussels resulted in a ban on their use as paintadditives except for ocean-going vessels. Several chaptersare devoted to regulatory policies for the use of organotincompounds, and to the acute effects of Bu3Sn– compoundson aquatic biota.

A number of chapters are devoted to the difficult task ofdeveloping reliable analytical methods for these lowconcentrations of organotin compounds; these includeconversion to organotin hydrides using NaBH4 or totetraorganotins using RMgX, followed by a separationtechnique (usually chromatography) and detection byatomic absorption or mass spectrometry. 14C-labelling ofBu3Sn– has also been employed; in addition, mussels havebeen used as bioindicators in order to overcome some ofthe limitations of chemical analysis.

Other chapters are concerned with the complex problemof the fate and persistence of Bu3Sn– in aqueousecosystems. Both aquatic plants and animals possessenzyme systems responsible for successive loss of butylgroups; this loss may be accompanied by biomethylation,since Bu3SnMe and Bu2SnMe2 have been detected.Free-radical biological hydroxylation of Bu–Sngroups also occurs, giving for example[CH3CH2CH(OH)CH2SnBu2]

+ . Metabolic studies on fishusing 14C-labelled Bu3Sn– have revealed a short residencetime of about three days.

Further chapters are concerned with the ways in whichthese varied chemical reactions occur and the time scaleinvolved. Reactions take place in the organic-rich surfacefilm of natural waters, the bulk aqueous medium and insediments. Biodegradation in sediments is possibly cata-lysed by clay minerals but is slow, and sediments providea short-term sink for Bu–Sn compounds. Photolyticdecomposition is probably confined to the surface layer. Ithas been firmly established that bacteria, algae and fungican degrade Bu3Sn–. A further point of general interest isthat the persistence of Bu3Sn– in aqueous ecosystems ismeasured in months, whereas many toxic chemicals suchas DDT persist for years.

Chemists may be a bit dismayed by the number andnature of errors in representing structural formulae, e.g. inFigs 1.2 and 18.2 and on p. 4 (the TBT++ ) cation, but thegeneral organization of this book is good and individualchapters are both stimulating and readable. A substantialand well-organized index is included.

F. GLOCKLING

University of Oxford, UK

Symmetry and StructureS. F. A. Kettle2nd edition, John Wiley and Sons, Chichester, 1995430 pages. £19.99ISBN 0-471-95476-4

The first edition of this book, subtitled Readable GroupTheory for Chemists, appeared in 1984, and the majorchanges in this new edition are added chapters on crystalsymmetry and space groups. The main competing text isCotton’s Chemical Applications of Group Theory and it isinteresting to compare the authors’ different approaches.Whereas Cotton launches quickly into formal definitionsof groups and the classification of point groups, Kettlestarts much more gently and leads the reader along withspecific examples rather than formal ideas. This has someconsequences which are surprising at first sight. Forexample, the identification of molecular point groups isnot discussed until the end of Chapter 7, by which timemost of the ideas about representations and charactertables have been fully developed.

For those who like a gentle approach, Kettle’s bookcertainly justifies its subtitle, and gives an excellentintroduction to the basic priniciples. The new chapters onspace groups follow a rather different format, being moreabstract and less based on examples, but are neverthelessvery clear and useful. I do find some disadvantages,however, with Kettle’s approach. The range of examplesdiscussed is very limited (often one molecule per chapter);in point groups these are mostly concerned with molecularorbitals; vibrations and spectroscopic selection rules aretreated much more briefly. Readers of this journal will bedisappointed to find no reference to organometalliccompounds. Also, it is not easy to look things up in thisbook—it really is intended to be read from the beginning.In summary, I recommend it as a very good book forstudents, but much less useful for reference purposes.

P. A. COX

University of Oxford, UK

756

© 1997 by John Wiley & Sons, Ltd. APPLIED ORGANOMETALLIC CHEMISTRY, VOL. 11, 755–756 (1997)