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Synlett 2011(16): 2315-2320  
DOI: 10.1055/s-0030-1261232
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient One-Pot Synthesis of Sulfonamides and Sulfonyl Azides from Thiols Using N-Chlorosuccinimide

Hojat Veisi*a,b, Ramin Ghorbani-Vagheic, Saba Hemmatia, Jafar Mahmoodic
a Department of Chemistry, Payame Noor University, 19395-4697 Tehran, I. R. of Iran
Fax: +98(838)4227463; e-Mail: hojatveisi@yahoo.com;
b Young Researchers Club, Kermanshah Branch, Islamic Azad University, Kermanshah, Iran
c Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran
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Publikationsverlauf

Received 19 June 2011
Publikationsdatum:
13. September 2011 (online)

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Abstract

A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel.

Key words

N-chlorosuccinimide - sulfonyl chlorides - sulfon­amides - sulfonyl azides

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