Novel Rearrangement of N-(9H-Carbazol-9-yl)arylaminyl Radicals

Article abstract of DOI:10.1021/jo00061a013

The title radicals were generated from 2-(arylazo)-2'-iodobiphenyls using the tin hydride method.When the aryl substituent has an acetyloxy or a benzoyloxy group in the ortho position, besides reduction of the hydrazyl radical, a migration of the acetyl or benzoyl from oxygen to nitrogen atom took place.The mechanism of the rearrangement is discussed, and evidences supporting a radical pathway are reported, including EPR characterization of the intermediates.