Issue 7, 2002
From the journal:

Chemical Communications

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

J. Matthew Wood,a   Paul S. Hinchliffe,a   Andy M. Davis,b   Rupert P. Austinb  and  Michael I. Page*a  

* Corresponding authors

a Department of Chemical and Biological Sciences, University of Huddersfield, Queensgate, Huddersfield, UK

b AstraZeneca R and D, Charnwood, Bakewell Road, Loughborough, UK

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

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Article information

DOI
https://doi.org/10.1039/B111340M
Article type
Communication
Submitted
12 Dec 2001
Accepted
20 Feb 2002
First published
12 Mar 2002

Chem. Commun., 2002, 772-773

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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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