REARRANGEMENT OF N-(TRIFLUOROMETHYL)ANTHRANILOYL FLUORIDE TO 2-(TRIFLUOROMETHYL)ANILINE - KINETIC AND MECHANISTIC OBSERVATIONS

Article abstract of DOI:10.1016/S0022-1139(00)80127-X

Pseudo first order rate constants for the rearrangement of N-(trifluoromethyl)anthraniloyl fluoride (2) to N-<(2-trifluoromethyl)phenyl>carbamoyl fluoride (3) in anhydrous HF have been determined.Increasing HF levels accelerate this process, but increasing KF concentrations retard the reaction.An ionic species has been proposed as the intermediate in the suggested mechanism.Further reaction of 3 with HF proceeded to give 2-(trifluoromethyl)aniline hydrofluoride (4) via an unprecedented expulsion of carbonyl fluoride.