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Chlorotrimethylsilane-Nitrate Salts as Oxidants: Direct Oxidative Conversion of Thiols and Disulfides to Sulfonyl Chlorides

G. K. Surya Prakash,* Thomas Mathew, Chiradeep Panja and George A. Olah

*Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, Email: gprakashusc.edu

G. K. S. Prakash, T. Mathew, C. Panja, G. A. Olah, J. Org. Chem., 2007, 72, 5847-5850.

DOI: 10.1021/jo070907g (free Supporting Information)


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Abstract

A mixture of nitrate salt and chlorotrimethylsilane is a mild and efficient reagent for the direct oxidative chlorination of thiols and disulfides to the corresponding sulfonyl chlorides in excellent yields. Sulfides and sulfoxides were also found to undergo oxidation to sulfones. In most cases these reactions are highly selective, simple, and clean, affording products in high yield and purity.

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Key Words

Oxidations, Chlorinations, Nitrate


ID: J42-Y2007-2350