Reexamination of the Thermolytic Rearrangement of 4-Halophenyl Azides to 2-Aminophenols and other Products

Article abstract of DOI:10.1007/BF00814133

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). Keywords: Acetylated-2-amino-5-halophenols; 2-Acetamido-5-haloanisoles; 6-Halo-2-methylbenzoxazoles; 6-Halobenzoxazolones; 6-Halotriacetylaminophenols; 1H-NMR spectra; Fungicidal activity.