Rearrangement of N-(trifluoromethyl)anthraniloyl fluoride to 2-(trifluoromethyl)aniline - kinetic and mechanistic observations

Pseudo first order rate constants for the rearrangement ofN-(trifluoromethyl)anthraniloyl fluoride (2) to N-[(2-trifluoromethyl)phenyl]carbamoylfluoride (3) in anhydrous HF havebeen determined. Increasing HF levels accelerate this process,but increasing KF concentrations retard the reaction. An ionicspecies has been proposed as the intermediate in the suggestedmechanism. Further reaction of 3 with HF proceeded to give2-(trifluoromethyl)aniline hydrofluoride (4) via an unprecedentedexpulsion of carbonyl fluoride.