Eliminations promoted by thiolate ions. Part III. Reactions of t-butyl chloride and t-butyldimethylsulphonium iodide

Abstract

The effect of the leaving group on the relative reactivities of benzenethiolate and alkoxide ions in bimolecular eliminations from t-butyl compounds is investigated. The substrates studied are t-butyl chloride and t-butyldimethylsulphonium iodide. There is a correlation between the relative reactivities of these bases and Brönsted β coefficients, obtained by using substituted benzenethiolates as bases, for the two reaction series. The variation of the rate ratio with the change in leaving group is explained in terms of alterations in the nature of the E2 transition states.