Base-catalyzed hydrolysis and carbonyl-18O exchange kinetics for toluamides containing amine portions of reduced basicity. N-Toluoyl-3,3,4,4-tetrafluoropyrrolidine and N-toluoylpyrrole

Base-catalyzed hydrolysis and 18 O=C exchange kinetics for N-toluoyltetrafluoropyrrolidine (IV) and N-toluoylpyrrole (V) have been determined as a function of [OH - ] at 73 and 25 o C respectively, μ=1.0 (KCl). Both amides exhibit k hyd vs [OH - ] profiles that contain first-order and second-order domains in [OH - ]. For IV at low [OH - ] where both the hydrolysis and exchange kinetics are first order in [OH - ], k ex /k hyd =9.0, and this value is progressively reduced as [OH - ] increases