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Conversion of bis(o-nitrophenyl)diselenides to heterocycles containing selenium and nitrogen with the aid of samarium diiodide

✍ Scribed by Xiaoyuan Chen; Weihui Zhong; Yongmin Zhang

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
207 KB
Volume
13
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Treatment of bis(o‐nitrophenyl)diselenides with SmI~2~ led to simultaneous reduction of nitro groups and reductive cleavage of SeSe bonds as well as to the formation of the intermediates 2. The intermediates 2 were “living” double‐anions formed in situ, and reacted readily with ω‐bromoketones and α‐bromocarboxylic acid derivatives to afford the desired 2H‐1,4‐benzoselenazines and 2H‐1,4‐benzoselenazin‐3(4H)‐ones, respectively, in moderate to high yields and under mild conditions. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:302–306, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10034

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Conversion of bis(o-nitrophenyl)disulfides to heterocycles containing sulfur and nitrogen by the action of samarium diiodide
✍ Weihui Zhong; Xiaoyuan Chen; Yongmin Zhang 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 78 KB

## Abstract Treatment of bis(o‐nitrophenyl)disulfides **1** with SmI~2~ led to simultaneous reduction of nitro groups and reductive cleavage of S–S bonds as well as the formation of the active intermediates **2**. The intermediates **2** reacted smoothly with aldehydes or ketones, acid chlorides or