Reexamination of the thermolytic rearrangement of 4-halophenyl azides to 2-aminophenols and other products / H. Gershon, D. D. Clarke, and M. Gershon, Department of Chemistry, Fordham University, Bronx, NY 10458, USA, New York Botanical Garden, Bronx, NY 10458, USA

The halogenation of derivatives of 2-aminophenol with N-chloro- and N-bromosuccinimides at ambient temperatures in acetic acid was studied. With the necessary compounds available, a reexamination of the thermolytic rearrangement of 2-halophenyl azides to 2-aminophenols and other products was undertaken. It is certain that the rearrangement of 4-halophenyl azides to 2-aminophenols occurs but the products identified in this study differ significantly from those reported previously by Suschitzky et al. (1963, 1966