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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

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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.

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
School of Applied Sciences > Biomolecular Sciences Research Centre
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References:

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CHEM. COMMUN., 2002, 772–773 773

Depositing User: Sara Taylor
Date Deposited: 14 Feb 2008 12:19
Last Modified: 20 Oct 2008 10:29
URI: http://eprints.hud.ac.uk/id/eprint/525

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