Catalyst-Free Efficient Regioselective Ring Opening of Oxiranes with Thioacids in Water

Abstract

Epoxide ring opening with thioacetic acid and thiobenzoic acid was investigated in the presence of water under catalyst-free conditions. This green and simple process gave an excellent yield. With simple decanting, the products were obtained in high purity and on a large scale. In this process, alkyl halide and ester cleavage were not observed.

Keywords:

• Epoxide
• ring opening
• thioacids
• water

ACKNOWLEDGMENT

Many thanks go to the Faculty of Chemistry of Tarbiat Moallem University for supporting this work.

Notes

^a Isolated yields.

^b Isolated yield for large-scale synthesis.

^c The yield in parentheses refers to the Michael adduct.