The anomalous reaction of p-Methoxy-β,β-dimethylstyrene with mercury(II) acetate in methanol

Abstract

The methoxymercurations of β, β-dimethylstyrene (7) and its p-nitro (12) and p-methoxy (13) derivatives with mercury(II) acetate in methanol are regiospecific and give methoxymercuration products in which the methoxy group is on the β-carbon. Demercuration of the adducts from (12) and (13) with alkaline borohydride proceeds normally, but the demercuration of the adduct from (7) gives considerable formation of the diastereoisomeric dimeric products (9a,b). The methoxymercuration product from (13) is surprisingly reactive and gives mercury or mercury(1) acetate and the vicinal diether 1,2-dimethoxy-1-(p-methoxyphenyl)-2-methylpropane (17).