Ionic Liquid Promoted Regio- and Stereo-Selective Thiolysis of Epoxides—A Simple and Green Approach to β-Hydroxy- and β-Keto Sulfides

Brindaban C. Ranu; Tanmay Mandal; Subhash Banerjee; Suvendu S. Dey

doi:10.1071/CH06434

RESEARCH ARTICLE

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Ionic Liquid Promoted Regio- and Stereo-Selective Thiolysis of Epoxides—A Simple and Green Approach to β-Hydroxy- and β-Keto Sulfides

Brindaban C. Ranu ^A ^B , Tanmay Mandal ^A , Subhash Banerjee ^A and Suvendu S. Dey ^A

+ Author Affiliations

- Author Affiliations

^A Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.

^B Corresponding author. Email: ocbcr@iacs.res.in

Australian Journal of Chemistry 60(4) 278-283 https://doi.org/10.1071/CH06434
Submitted: 16 November 2006 Accepted: 6 February 2007 Published: 26 April 2007

Abstract

A variety of epoxides underwent facile cleavage by thiols under the catalysis of 1-methyl-3-butylimidazolium bromide, [bmIm]Br, to produce the corresponding β-hydroxy sulfides with high regio- and stereo-selectivity. On the other hand, a specially designed basic ionic liquid, [bmIm]OH, efficiently catalyzes the thiolysis of α,β-epoxy ketones providing β-keto sulfides through simultaneous retro-aldol cleavages. The reactions are clean, high yielding, and do not require any organic solvent. The catalyst is also recycled.

Acknowledgments

This work has enjoyed financial support from CSIR, New Delhi [grant no. 01(1936)/04]. T.M., S.B., and S.S.D. are also thankful to CSIR for their fellowships.

References

Ionic Liquid Promoted Regio- and Stereo-Selective Thiolysis of Epoxides—A Simple and Green Approach to β-Hydroxy- and β-Keto Sulfides

Abstract

Acknowledgments

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