Magnesium Chloride–Catalyzed Thiolysis of Epoxides: Synthesis of β-hydroxy Sulfides

Abstract

A mild and convenient ring opening of epoxides with thiophenol and its derivatives takes place at room temperature in the presence of magnesium chloride as catalyst to afford the corresponding β-hydroxy sulfides along with minor amounts of 2-chlorocycloalkanols in good yields. When the crude reaction mixtures are treated with aqueous sodium hydroxide solution, pure 2-arlythiocycloalkanols are obtained in good yields.

Keywords:

• Epoxides
• β-hydroxy sulfides
• ring opening
• thiols

ACKNOWLEDGMENTS

We thank the Department of Science and Technology (DST), New Delhi, for providing financial assistance. R. R. thanks the DST and J. A. thanks the University Grants Commission, New Delhi, for the fellowship awards.

Notes

^a The reactions were carried out with 2 mM epoxide and 2 mM of arenethiol 2 in the presence of 0.4 mM of MgCl₂ in 5 mL of dichloromethane (see the Experimental section).

^b Yield was calculated assuming the material as 3 or 4.

^c Ratio was determined by ¹H NMR (500-MHz) analysis.

^d Yield of pure and isolated products 3 or 4.