An activated sulfonylating agent that undergoes general base-catalyzed hydrolysis by amines in preference to aminolysis

WY Tsang, N Ahmed, K Hemming…

Index: Tsang, Wing-Yin; Ahmed, Naveed; Hemming, Karl; Page, Michael I. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 24 p. 3993 - 4000

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Citation Number: 11

Abstract

Activated sulfonyl derivatives, similar to acyl ones, usually undergo aminolysis with amines in water as nucleophilic attack by the amine is preferred to hydrolysis. However, despite being active sulfonyl derivatives, four-membered heterocyclic sulfonamides, β-sultams, do not undergo aminolysis in aqueous solution but preferentially react to give hydrolysis products only. The rate of the reaction of β-sultams in buffered solutions of simple primary ...