Kinetics of α-chlorination of sulphoxides by iodobenzene dichloride

Abstract

The kinetics of the reaction of sulphoxides with iodobenzene dichloride and pyridine in acetonitrile to give α-chloro-sulphoxides has been studied. The data indicate that the reaction proceeds through α-chlorosulphoxonium salts which by attack of base collapse to α-chlorosulphoxides. The last step is rate-determining for substrates deactivated by electron-withdrawing and sterically hindered groups.