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

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.

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