Sodium p-toluenesulfinate/copper(II) acetate in free radical reactions of 5-aryl substituted alkenes

Sheow Fong Wang, Che Ping Chuang, Jia Han Lee, Shui Te Liu

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

p-Toluenesulfonyl radical can be generated from sodium p- toluenesulfinate in aqueous acetic acid or formic acid. Sulfonyl radical mediating reaction of 5-aryl substituted alkenes with sodium p- toluenesulfinate/copper(II) acetate gave p-toluenesulfonylmethyl substituted naphthalene and isoquinoline derivatives. This reaction proceeded much faster in aqueous formic acid than in aqueous acetic acid. The cyclization mode (Ar2-6 vs Ar1-5) of the 5-phenyl-1-butyl radical is strongly dependent on the geometry of the tether of the radical intermediate.

Original languageEnglish
Pages (from-to)2273-2288
Number of pages16
JournalTetrahedron
Volume55
Issue number8
DOIs
Publication statusPublished - 1999 Feb 19

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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