A Review of Organotin Compounds: Chemistry and Applications

Abstract

Organotin compounds find a bigger range of technological and industrial applications than the organic compounds of any other metal. Many of these applications involve catalysis or anticatalysis, often in polymer chemistry, and they have an importance out of all proportion to the tonnage of tin which is used. This article reviews the present standing of the non-biological applications of organostannanes, with an emphasis on the mechanisms of the reactions which are involved. The three major families of organometallic compounds which find application in technology and industry are those based on aluminium, silicon, and tin. Alkylaluminium compounds are highly reactive, and their applications depend on their chemical properties as alkylating agents, for example towards tin tetrachloride in the production of alkyltin compounds. Organotin compounds were first studied in 1852 by Löwig, who prepared diethyltin by the action of a sodium-tin alloy upon ethyl iodide. In the following year Frankland prepared tetraethyltin and in the next years a considerable number of both alkyl and aryl organotin compounds were synthesized and described. In the course of these studies more than one of the investigators became aware of the poisonous nature of some of these compounds and Frankland himself was made ill for several months, but happily recovered, and there are no reports that any of those affected actually succumbed. It was evident that certain organotin compounds, notably triethyltin hydroxide and triethyltin acetate, were highly toxic; this was confirmed in 1881 by White, who studied their effects upon dogs and other animals. A period of 70 years was to elapse before the significance of these preliminary observations was realized.