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

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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 gprakash@usc.edu

J. Org. Chem., 2007, 72 (15), pp 5847–5850

DOI: 10.1021/jo070907g

Publication Date (Web): June 22, 2007

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

A mixture of nitrate salt and chlorotrimethylsilane is found to be a mild and efficient reagent for the direct oxidative conversion of thiols (1) and disulfides (2) to the corresponding sulfonyl chlorides (3) in excellent yields through oxidative chlorination. Sulfides and sulfoxides were also found to undergo oxidation to sulfones under similar reaction conditions. In most cases these reactions are highly selective, simple, and clean, affording products in high yield and purity.

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Citing Articles

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

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Development of an Extremely Efficient Oxidative Chlorination Reaction: The Value of Routine Data Collection
Neil Barnwell, Philip Cornwall, Daniel Horner, Jason Knott and John Liddon
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  This contribution describes the development of an extremely efficient process for the oxidative chlorination of a benzyl, alkyl thioether to yield an alkylsulfonyl chloride. This process was subsequently run on >100 kg scale. The product alkylsulfonyl ...
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Direct Conversion of Thiols to Sulfonyl Chlorides and Sulfonamides
Kiumars Bahrami, Mohammad M. Khodaei and Mehdi Soheilizad
The Journal of Organic Chemistry2009 74 (24), 9287-9291
- Direct Conversion of Thiols to Sulfonyl Chlorides and Sulfonamides
  Kiumars Bahrami, Mohammad M. Khodaei and Mehdi Soheilizad
  The Journal of Organic Chemistry2009 74 (24), 9287-9291
  H2O2 in combination with SOCl2 proved to be a highly reactive reagent for the direct oxidative conversion of thiol derivatives to the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Upon reaction with amines, the ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links