NOVEL REARRANGEMENT OF N-(9H-CARBAZOL-9-YL)ARYLAMINYL RADICALS

Authors
LEARDINI R LUCARINI M NANNI A NANNI D PEDULLI GF TUNDO A ZANARDI G
Citation
R. Leardini et al., NOVEL REARRANGEMENT OF N-(9H-CARBAZOL-9-YL)ARYLAMINYL RADICALS, Journal of organic chemistry, 58(9), 1993, pp. 2419-2423
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
9
Year of publication
1993
Pages
2419 - 2423
Database
ISI
SICI code
0022-3263(1993)58:9<2419:NRONR>2.0.ZU;2-1
Abstract
The title radicals were generated from 2-(arylazo)-2'-iodobiphenyls us ing 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 discu ssed, and evidences supporting a radical pathway are reported, includi ng EPR characterization of the intermediates.