Issue 7, 2002

Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group

Abstract

The alkaline hydrolysis of N-α-methoxycarbonyl benzyl-ß-sultam occurs 103 times faster than the corresponding carboxylate and with rapid D-exchange at the α-carbon: the pH rate profile indicates pre-equilibirum CH ionisation and together with formation of benzoyl formate as a product this suggests a novel mechanism for hydrolysis.

Graphical abstract: Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group

Additions and corrections

Article information

Article type
Communication
Submitted
12 Dec 2001
Accepted
20 Feb 2002
First published
12 Mar 2002

Chem. Commun., 2002, 772-773

Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group

J. M. Wood, P. S. Hinchliffe, A. M. Davis, R. P. Austin and M. I. Page, Chem. Commun., 2002, 772 DOI: 10.1039/B111340M

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