Acyl vs Sulfonyl Transfer in N-Acyl β-Sultams and 3-Oxo-β-sultams

Naveed Ahmed, Wing Y. Tsang, Michael I. Page

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

(Matrix presented) N-Acylsulfonamides usually react with nucleophiles by acyl transfer and C-N bond fission. However, the hydrolysis of N-acyl β-sultams is a sulfonyl transfer reaction that occurs with S-N fission and opening of the four-membered ring. Similar to other β-sultams, the N-acyl derivatives are at least 106-fold more reactive than N-acyl sulfonamides. 3-Oxo-β-sultams are both β-lactams and β-sultams but also hydrolyze with preferential S-N bond fission.

Original languageEnglish
Pages (from-to)201-203
Number of pages3
JournalOrganic Letters
Volume6
Issue number2
Early online date25 Dec 2003
DOIs
Publication statusPublished - 22 Jan 2004

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