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

doi:10.1039/a705416e

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 journal › Article › peer-review

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 language	English
Pages (from-to)	2037-2038
Number of pages	2
Journal	Chemical Communications
Issue number	21
DOIs	https://doi.org/10.1039/a705416e
Publication status	Published - 1 Jan 1997

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

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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AU - Baxter, Nicholas J.

AU - Laws, Andrew P.

AU - Rigoreau, Laurent

AU - Page, Michael I.

PY - 1997/1/1

Y1 - 1997/1/1

N2 - 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.

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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U2 - 10.1039/a705416e

DO - 10.1039/a705416e

M3 - Article

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SP - 2037

EP - 2038

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 21

ER -

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

Abstract

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