Reactions of thiolsulphonates with amines

Abstract

The equilibrium constants for the reaction of morpholine with methyl or t-butyl toluene-p-thiolsulphonates have been measured in acetonitrile–water (7 : 1,v/v) at 25 °C. Contrary to previous data they are 2·5 × 10^–3 and 3·4 for the methyl and t-butyl substrates respectively. In the same solvent medium have been measured the reaction rates and the activation parameters of the nucleophilic displacement reaction of morpholine with the same substrates. The overall mechanism is discussed.