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

Research output: Contribution to journalArticle

9 Citations (Scopus)

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.

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

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Cations
Hydrolysis
Substitution reactions
Positive ions
Acids
Ions
Kinetic parameters
hydroxide ion
naphthosultone

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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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Evidence for a trigonal bipyramidal intermediate during nucleophilic substitution at a sulfonyl centre and for a sulfonylium cation in the acid catalysed reaction. / Baxter, Nicholas J.; Laws, Andrew P.; Rigoreau, Laurent; Page, Michael I.

In: Chemical Communications, No. 21, 01.01.1997, p. 2037-2038.

Research output: Contribution to journalArticle

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AU - Page, Michael I.

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AB - 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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