Easy and environmentally friendly uncatalyzed synthesis of β-hydroxy arylsulfides by thiolysis of 1,2-epoxides in water

Abstract

The title compounds were prepared via thiolysis of alkyloxiranes by arylthiols in basic aqueous medium at 30 °C. The nucleophilic addition is anti diastereoselective and occurs on the less substituted carbon of the oxirane ring. The aqueous medium was reused and crystalline sulfides were isolated by filtration carrying out a solventless process. The protocol was used for a one-pot synthesis of hexahydrodibenzo[1,4]oxathiepinone 9.