Convenient Synthesis of 2, 4-Cyclohexadien-1-ones by Regioselective Methylthiomethylation of Phenols

Abstract

A convenient synthesis of a variety of 2, 4-cyclohexadien-1-ones 3-7 is described. Reaction of various phenols 2 having appropriate substituents with an excess of S, S-dimethylsuccinmidosulfonium chloride (Corey-Kim reagent, 1)in the presence of triethylamine proceeded with regioselective methylthiomethylation to give methylthiomethyl, bis(methylthiomethyl), or tris(methylthiomethyl)-2, 4-cyclohexadien-1-ones 3-7 in satisfactory yields.