The α-effect in benzyl transfers from benzylphenylmethyl sulfonium salts to N-methylbenzohydroxamate anions

K. R. Fountain, Darlene B. Tad-Y, Timothy W. Paul, Mikhail V. Golynskiy

Research output: Contribution to journalArticle

Abstract

The investigation of the occurrence of the α-effect in group transfers from phenyldialkyl sulfonium ions where one alkyl group is benzyl allows an assay of the effect of changing the nature of the C atom being transferred. The size of the α-effect responds to increasing electron demand, as methyl transfers do. Quantitative relationships between the size of the α-effect are established from both the nucleophilic side and the leaving group side of the S(N)2 transition state.

Original languageEnglish (US)
Pages (from-to)6547-6553
Number of pages7
JournalJournal of Organic Chemistry
Volume64
Issue number18
DOIs
StatePublished - Sep 3 1999

ASJC Scopus subject areas

  • Organic Chemistry

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