DOI: 10.1039/A705416E
(Paper)
Reference Section for: Chem. Commun., 1997, 2037-2038
Evidence for a trigonal bipyramidal intermediate during nucleophilic substitution at a sulfonyl centre and for a sulfonylium cation in the acid catalysed reaction
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Nicholas J. Baxter and Michael I. Page
Abstract
The rate of alkaline hydrolysis of a substituted β-sultam shows a dominant term second-order in hydroxide ion, clearly indicating the reversible formation of a monoanionic trigonal bipyramidal intermediate; substituent effects and kinetic parameters for the acid catalysed hydrolysis are indicative of the formation of a sulfonylium ion intermediate.
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