ChemInform Abstract: Sodium p-Toluenesulfinate/Copper(II) Acetate in Free Radical Reactions of 5-Aryl Substituted Alkenes.
✍ Scribed by Sheow-Fong Wang; Che-Ping Chuang; Jia-Han Lee; Shui-Te Liu
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 36 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Sodium p-Toluenesulfinate/Copper(II) Acetate in Free Radical Reactions of 5-Aryl Substituted Alkenes.
-Toluenesulfonylmethylsubstituted naphthalene and isoquinoline derivatives are obtained by the title reaction in good to excellent yields. The reaction proceeds much faster in aqueous formic acid (8-14 h) than in aqueous acetic acid (2-4 days). The cyclization mode (Ar 2 -6 versus Ar 1 -5) of the intermediate 5-arylbutyl radical is strongly dependent on the geometry of the tether of the radical intermediate. In this way, benzamides (VII) having electron-withdrawing groups on the benzene ring give sulfonamides (VIII) as major products as the result of a preference of Ar 1 -5 intramolecular over Ar 2 -6 cyclization. -(WANG, SHEOW-FONG;