Alkylation of several nucleophiles with alkylsulfonium salts.

K Umemura, H Matsuyama, N Kamigata

Index: Umemura, Kazuyuki; Matsuyama, Haruo; Kamigata, Nobumasa Bulletin of the Chemical Society of Japan, 1990 , vol. 63, p. 2593 - 2600

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Citation Number: 25

Abstract

The reactions of dialkylphenylsulfonium salts (1) with several nucleophiles such as phenols, amine, enolate ion, and thiolate ions, have been investigated. The relative reactivities of the alkyl groups of sulfonium salts for the phenolate ion (hard nucleophile) were as follows; Me: Et: i-Pr= 1.0: 1.34: 3.44. In the alkylation of the p-toluenethiolate ion (soft nucleophile) with 1, the opposite reactivity (Me: Et: i-Pr= 1.0: 0.22: 0.03) was found. When a sulfonium salt (1e) ...