Cine-Substitution in the thiophen series; the behaviour of 4-nitro-3-thienyl phenyl sulphone towards sodium arenethiolates in methanol

Abstract

4-Nitro-3-thienyl phenyl sulphone (3) reacts with various sodium arenethiolates in methanol to give 5-arylthio-3-thienyl phenyl sulphones (4)(main products) and 2-arylthio-4-nitrothiophens (2). An anomalous addition–elimination mechanism is suggested to account for the formation of the cine-substitution products (2) and (4).