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

Wood, J. Matthew, Hinchliffe, Paul S., Davis, Andrew M., Austin, Rupert P. and Page, Michael I. (2002) Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group. Chemical Communications. pp. 772-773. ISSN 1364-548X
Abstract

The alkaline hydrolysis of N--methoxycarbonyl benzyl-ß-sultam occurs 103 times faster than the corresponding carboxylate and with rapid D-exchange at the -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.

Information
URI:
https://eprints.hud.ac.uk/id/eprint/525
Title:
Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group
Creators:
Wood, J. Matthew, Hinchliffe, Paul S., Davis, Andrew M., Austin, Rupert P. and Page, Michael I.
Identification Number:
10.1039/b111340m
Official URL:
http://www.rsc.org/Publishing/Journals/CC/article....
Date:
2002
Subjects:
Q Science > Q Science (General)
Q Science > QD Chemistry
Schools:
School of Applied Sciences
School of Applied Sciences > Biomolecular Sciences Research Centre
Library
Item Type:
Article
Depositing User:
Sara Taylor
Date Deposited:
14 Feb 2008 12:19
Revision:
20
Last Modified:
28 Aug 2021 10:38
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