Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Preparation of Iminosulfonic Acid Derivatives by Means of Sulfinamides and N-Bromosuccinimide
Hisashi TakeiItaru WatanabeTeruaki Mukaiyama
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1965 Volume 38 Issue 11 Pages 1989-1993

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Abstract

It has been found that N-substituted benzenesulfinamides (I) react with thionyl chloride to give benzenesulfinyl chloride and the corresponding N-sulfinylamines, and that they are oxidized by treatment with bromine in an alkaline solution to give N-substituted sulfonamides.
When these benzenesulfinamides are treated with bromine or N-bromosuccinimide (NBS) in the presence of various primary or secondary amines, the corresponding benzeneiminosulfonamides are obtained in high yields. Similarly, the reaction of I, NBS and sodium p-nitrophenolate or sodium benzoate yields p-nitrophenyl benzeneiminosulfonate or N-benzoylbenzensulfonamide. These reactions are considered to proceed through the benzeneiminosulfonyl bromides formed by the oxidation of sulfinamides with bromine or NBS.

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