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.
Wood
J Matthew
JM
Department of Chemical and Biological Sciences, University of Huddersfield, Queensgate, Huddersfield, UK HD1 3DH.
Hinchliffe
Paul S
PS
Davis
Andy M
AM
Austin
Rupert P
RP
Page
Michael I
MI