Orientation in the Wallach Rearrangement for the Naphthyl Azoxy Series

Abstract

The acid-catalyzed Wallach rearrangement of azoxybenzenes has been extended to the naphthyl azoxy series in order to evaluate the effect of annelation of benzene rings on the course of rearrangement. The six known azoxy derivatives containing the α-naphthyl, β-naphthyl, and phenyl moieties, in various combinations, have been examined with respect to product orientation in moderately strong sulfuric acid solutions. The course of rearrangement (eqs. 2–6) is discussed on the basis of current mechanisms.