Elsevier

Tetrahedron Letters

Volume 51, Issue 40, 6 October 2010, Pages 5258-5261
Tetrahedron Letters

Reactions of selenium dichloride and dibromide with divinyl sulfone: synthesis of novel four- and five-membered selenium heterocycles

https://doi.org/10.1016/j.tetlet.2010.07.133Get rights and content

Abstract

The reactions of selenium dichloride and dibromide with divinyl sulfone leading to novel selenium heterocycles, 2,4-bis(halomethyl)-1,3-thiaselenetane-1,1-diones and 5-halo-2-halomethyl-1,3-thiaselenolane-1,1-diones, have been studied. Under the action of silica gel or pyridine, 5-halo-2-halomethyl-1,3-thiaselenolane-1,1-diones undergo facile regioselective dehydrohalogenation into 5-halo-2-methylene-1,3-thiaselenolane-1,1-diones.

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Acknowledgment

Financial support from the Russian Foundation for Basic Research (Grants No. 10-03-00543 and 10-03-92666) is gratefully acknowledged.

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