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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 12
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Original Articles

Oxidation of Sulfides with N‐Bromosuccinimide in the Presence of Hydrated Silica Gel

Mohammed Hashmat Ali Department of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri, USACorrespondence[email protected]
,
Melanie Hartman Department of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri, USA
,
Kimberly Lamp Department of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri, USA
,
Chad Schmitz Department of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri, USA
&
Tim Wencewicz Department of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri, USA
Pages 1769-1777 | Received 07 Dec 2005, Published online: 22 Aug 2006
 
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Abstract

An efficient and highly selective procedure for oxidation of sulfides to sulfoxides with N‐bromosuccinimide (NBS) in the presence of hydrated silica gel has been developed. Hydrated silica gel supplies the water necessary for decomposition of the intermediate bromosulfonium salt to the product, allowing the reaction to employ a nonaqueous media. Also, this procedure has increased the scope of the reaction by oxidizing a wider variety of sulfides, which was not possible until now.

Acknowledgement

M.H.A. thanks Bjorn Olesen for help during preparation of this manuscript.

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