Synthesis 2003(10): 1503-1505
DOI: 10.1055/s-2003-40530
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes with in situ Generated Carbanions of 1-Methyl-3-chloro-1,3-dihydro-2,1-benzisothiazole 2,2-Dioxides

Krzysztof Wojciechowski*, Helena Modrzejewska
Institute of Organic Chemistry Polish Academy of Sciences, ul. Kasprzaka 44/52, P.O.Box 58, 01-224 Warszawa, Poland
Fax: +48(22)6326681; e-Mail: kris@icho.edu.pl;
Further Information

Publication History

Received 1 April 2003
Publication Date:
08 July 2003 (online)

Abstract

Base-induced transformation of an equimolar mixture of 1-alkyl-1,3-dihydro-2,1-benzisothiazole 2,2-dioxides (benzosul­tams) and their 3,3-dichloro derivatives furnishes 1-alkyl-3-chloro-1,3-dihydro-2,1-benzisothiazole 2,2-dioxides which react with nitroarenes according to the vicarious nucleophilic substiution of hydrogen (VNS) mechanism giving 3-(nitroaryl)benzosultams.