Oxidative Generation of Thioalkyl Cations from 2-Tributylstannyl-1, 3-dithianes and 1-(Tributylstannyl) alkyl Sulfides and Their Reactions with Olefinic Nucleophiles.

K Narasaka, N Arai, T Okauchi

Index: Narasaka, Koichi; Arai, Noriyoshi; Okauchi, Tatsuo Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 10 p. 2995 - 3003

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Citation Number: 32

Abstract

2-Tributylstannyl-1, 3-dithianes and 1-(tributylstannyl) alkyl sulfides are oxidized with ammonium hexanitratocerate (IV) or ferrocenium hexafluorophosphate to generate their cation radicals, which dissociate into the carbocations and tributylstannyl radical. The carbocations thus generated react with olefinic nucleophiles to afford the corresponding addition products in good yield.