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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