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

doi:10.1016/S0040-4020(99)00027-7

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	2273-2288
Number of pages	16
Journal	Tetrahedron
Volume	55
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4020(99)00027-7
Publication status	Published - 1999 Feb 19

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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

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.",

author = "Wang, {Sheow Fong} and Chuang, {Che Ping} and Lee, {Jia Han} and Liu, {Shui Te}",

year = "1999",

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T1 - Sodium p-toluenesulfinate/copper(II) acetate in free radical reactions of 5-aryl substituted alkenes

AU - Wang, Sheow Fong

AU - Chuang, Che Ping

AU - Lee, Jia Han

AU - Liu, Shui Te

PY - 1999/2/19

Y1 - 1999/2/19

N2 - 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.

AB - 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.

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JO - Tetrahedron

JF - Tetrahedron

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