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Direct Synthesis of Functionalized Unsymmetrical beta-Sulfonamido Disulfides by Tetrathiomolybdate Mediated Aziridine Ring-Opening Reactions

Sureshkumar, Devarajulu and Ganesh, Venkataraman and Vidyarini, Ravindran Sasitha and Chandrasekaran, Srinivasan (2009) Direct Synthesis of Functionalized Unsymmetrical beta-Sulfonamido Disulfides by Tetrathiomolybdate Mediated Aziridine Ring-Opening Reactions. In: Journal of the Organic Chemistry, 74 (20). pp. 7958-7961.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo901528e

Abstract

Direct synthesis of unsymmetrical beta-sulfonamido disulfides by ring-opening of aziridines by using benzyltriethyl-ammonium tetrathiomolybdate 1 as a sulfur transfer reagent in the presence of symmetrical disulfides as thiol equivalents has been reported. Reaction of benzyl and alkyl disulfides gave unsymmetrical beta-sulfonamido disulfides as the only product in very good yields. From the Study, it has been observed that aryl disulfides containing p-NO2, p-Cl, and p-CN led to the formation of the corresponding beta-aminosulfides as the exclusive products. However, un-substituted aryl disulfides and the one containing electron-donating substituents (p-Me) provide a mixture of beta-sulfonamido mono- and disulfides as the products.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 29 Oct 2009 06:24
Last Modified: 19 Sep 2010 05:50
URI: http://eprints.iisc.ernet.in/id/eprint/24528

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