Synlett

Novel N-dealkylation of N-alkyl sulfonamides and N, N-dialkyl sulfonamides with periodic acid catalyzed by chromium (III) acetate hydroxide

L Xu, S Zhang, ML Trudell

Index: Xu, Liang; Zhang, Suhong; Trudell, Mark L. Synlett, 2004 , # 11 p. 1901 - 1904

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Citation Number: 2

Abstract

Initially, the oxidative dealkylation of N-alkyl benzenesulfonamides with periodic acid catalyzed by chromium(III) acetate hydroxide [Cr 3 (OAc) 7 (OH) 2 ] was examined (Table [1] ). The reactions were conveniently performed by stirring a solution of N-alkyl benzenesulfonamide, H 5 IO 6 and Cr 3 (OAc) 7 (OH) 2 in acetonitrile at room temperature. N-Alkyl benzenesulfonamides with primary alkyl as well as secondary alkyl chains were easily dealkylated to yield ...

~72%

~85%

~91%

~75%

~91%

~82%

~88%

~81%

~92%

~89%

~89%

~82%

~84%

~84%

~81%

~84%

~92%

~77%

~90%

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