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Synthesis 2012(2): 316-322  
DOI: 10.1055/s-0031-1289628
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Sulfonyl Chlorides and Sulfonic Acids in SDS Micelles

Kiumars Bahrami*a,b, Mohammad M. Khodaei*a, Jamshid Abbasia
a Department of Organic Chemistry, Faculty of Chemistry, Razi University, Kermanshah 67149-67346, Iran
Fax: +98(831)4274559; e-Mail: kbahrami2@hotmail.com; e-Mail: mmkhoda@razi.ac.ir;
b Nanoscience and Nanotechnology Research Center (NNRC), Razi University, Kermanshah 67149-67346, Iran
Further Information

Publication History

Received 21 September 2011
Publication Date:
30 November 2011 (online)

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Abstract

H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and di­sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.

Key words

micelles - oxidation - hydrogen peroxide - thiols - solvent systems - amphiphiles

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