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) ...
