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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 11
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Original Articles

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

, , , &
Pages 1638-1643 | Received 26 Sep 2009, Published online: 20 Apr 2011
 

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.

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.

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