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Original Articles

Fast and efficient green synthesis of thiosulfonate S-esters by microwave-supported permanganate oxidation of symmetrical disulfides

, , , &
Pages 340-350 | Received 20 Jan 2015, Accepted 28 Feb 2015, Published online: 09 Apr 2015
 

Abstract

Potassium permanganate absorbed on copper(II) sulfate pentahydrate has been found to be an efficient, inexpensive, and green oxidation agent for the synthesis of “symmetrical” thiosulfonate S-esters by oxidation of the corresponding symmetrical disulfides. The oxidation reactions were carried out under solvent-free reaction conditions within 15 min under the influence of microwave irradiation, as well as (for comparison) supported by conventional heating, to afford yields of the thiosulfonate S-esters in the range of 60–83%. The oxidation reaction appears to proceed (at least partly) via an intermediate symmetrical vic-disulfoxide.

GRAPHICAL ABSTRACT

Funding

The authors are grateful to the Vietnamese National Foundation for Science and Technology Development (NAFOSTED) for financial support under grant number [104.01–2011.40]. The authors are also indebted to the Danish International Development Agency (DANIDA) for financial support via the Enhancement of Research Capacity (ENRECA) programme.

Supplemental data

Supplemental data for this article can be accessed at doi:10.1080/17415993.2015.1025404

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