Evidence for a trigonal bipyramidal intermediate during nucleophilic substitution at a sulfonyl centre and for a sulfonylium cation in the acid catalysed reaction

Nicholas J. Baxter, Andrew P. Laws, Laurent Rigoreau, Michael I. Page

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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.

Original languageEnglish
Pages (from-to)2037-2038
Number of pages2
JournalChemical Communications
Issue number21
Publication statusPublished - 1 Jan 1997


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