Wagner-Meerwein Rearrangement of Allylbenzene Derivatives. I. Bromination of Safrole

Abstract

The reaction of safrole (I) with bromine (II) was examined giving different results from the literature, i.e., 2, 3-dibromo-1-(3', 4'-methylenedioxyphenyl) propane (III), 1, 3-dibromo-2-(3', 4'-methylenedioxyphenyl) propane (V) and their bromo-substituted derivatives (IV and VI) were obtained. The formation of rearranged adducts (V and VI) suggests that Wagner-Meerwein rearrangement occured during this addition. The relationship between the reaction conditions and the ratio of the products was investigated.