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Synthesis 2001(11): 1659-1664
DOI: 10.1055/s-2001-16764
PAPER
© Georg Thieme Verlag Stuttgart · New York

Selective Synthesis of 1,2-Benzisothiazol-3-one-1-Oxide Nitro Derivatives

Evgeny A. Serebryakov, Pavel G. Kislitsin, Victor V. Semenov, Sergey G. Zlotin*
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt, 47, 119991, Moscow, Russia
Fax: +7(095)1355328; e-Mail: zlotin@cacr.ioc.ac.ru;
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Publication History

Received 21 March 2001
Publication Date:
12 August 2004 (online)

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Abstract

A new selective synthesis of 1,2-benzisothiazol-3-one-1-oxide nitro derivatives by reaction of 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in wet CH2Cl2 has been developed. Reactions of N-unsubstituted 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in 60% AcOH give, instead of the S-oxides, the appropriate 1,2-benzisothiazol-3-one-1,1-dioxide nitro derivatives.

Key words

polynitrobenzamides - chlorine - 1,2-benzisothiazole-3-one-1-oxides - 1,2-benzisothiazole-3-one-1,1-dioxides

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