Hydrolysis rates of alkyl and aryl sulfinamides

evidence of general acid catalysis

Andrew M. Piggott, Peter Karuso*

*Corresponding author for this work

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Sulfinamides are important in enantioselective synthesis, as rare post-translational modifications of proteins and as isosteres of the amide bond. Little is known about the rates of hydrolysis for aliphatic sulfinamides or the mechanism of hydrolysis. In this Letter, we show that sulfinamides hydrolyse by predominantly a non-specific acid/base catalysis with phosphate buffer but by varying the buffer concentration, it was possible to determine the hydrolysis rates of a range of sulfinamides with water through non-linear least squares regression.

Original languageEnglish
Pages (from-to)7452-7455
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number42
DOIs
Publication statusPublished - 15 Oct 2007

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