Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group.
The alkaline hydrolysis of N-alpha-methoxycarbonyl benzyl-beta-sultam occurs 10(3) times faster than the corresponding carboxylate and with rapid D-exchange at the alpha-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.
Department of Chemical and Biological Sciences, University of Huddersfield, Queensgate, Huddersfield, UK HD1 3DH.
J Matthew
JM
Wood
Paul S
PS
Hinchliffe
Andy M
AM
Davis
Rupert P
RP
Austin
Michael I
MI
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