(Bromodimethyl)sulfonium Bromide–Mediated Thiolysis of Epoxides: An Easy Access to β-Hydroxy Sulfides and Benzoxathiepinones in Solvent-Free Conditions

Abstract

A mild, rapid and highly regioselective opening of epoxides by mercaptans to β-hydroxy sulfides and benzoxathiepinones has been achieved in excellent yields, using catalytic amount of (bromodimethyl)sulfonium bromide in solvent free reaction conditions.

Keywords:

• (Bromodimethyl)sulfonium bromide
• epoxides
• β-hydroxy sulfides
• solvent-free reactions
• thiols

ACKNOWLEDGMENTS

The authors thank Director, IICT for facilities, and M. S. thanks CSIR for the financial support.

Notes

Reported compounds are indicated by the references in brackets in the yields column.

*Determined by HPLC apparatus fitted with a chiralcel OJ-H chiral column (i-prOH/hexane = 1/99; flow rate 0.8 ml/min; detector = 254 nm).

*Reaction done in solvent (ethanol).

Presented at the Asian Symposium on Medicinal Plants, Spices and Other Natural Products (ASOMPS-XIII), Indian Institute of Chemical Technology, Hyderabad, India, November 3–6, 2008.