Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group

J. Matthew Wood, Paul S. Hinchliffe, Andy M. Davis, Rupert P. Austin, Michael I. Page

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The alkaline hydrolysis of N-α-methoxycarbonyl benzyl-β-sultam occurs 103 times faster than the corresponding carboxylate and with rapid D-exchange at the α-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.

Original languageEnglish
Pages (from-to)772-773
Number of pages2
JournalChemical Communications
Issue number7
Early online date12 Mar 2002
DOIs
Publication statusPublished - 7 Apr 2002

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formic acid
Sulfonamides
Hydrolysis
Ionization
Carbon
naphthosultone

Cite this

Wood, J. Matthew ; Hinchliffe, Paul S. ; Davis, Andy M. ; Austin, Rupert P. ; Page, Michael I. / Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group. In: Chemical Communications. 2002 ; No. 7. pp. 772-773.
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Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group. / Wood, J. Matthew; Hinchliffe, Paul S.; Davis, Andy M.; Austin, Rupert P.; Page, Michael I.

In: Chemical Communications, No. 7, 07.04.2002, p. 772-773.

Research output: Contribution to journalArticle

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