Triton B promoted highly regio- and chemoselective ring opening of epoxides with 2-aminobenzenethiol under solvent-free conditions

Abstract

A simple and highly efficient synthesis of amino-β-hydroxysulfides has been carried out ring opening of epoxides with 2-aminobenzenethiol with catalytic amount of benzyl trimethylammonium hydroxide (Triton B) under solvent-free conditions. Excellent regioselectivity was achieved for aliphatic unsymmetrical epoxides, with nucleophilic attack at the less hindered carbon atom of the epoxide. In the case of styrene oxide the nucleophilic attack takes place exclusively on the more substituted carbon. This process was also regio-and chemo-selective as illustrated using epichlorohydrin with two epoxide ring positions and 2-aminobenzenethiol with two functional groups (SH and NH2).