Kinetics of trans-cinnamic anhydride reactions catalyzed by pyridine, 4-dimethylaminopyridine, and N-methylimidazole.
The kinetics of hydrolysis of trans-cinnamic anhydride and of its reactions with hydroxy compounds were studied in the presence of pyridine, 4-dimethylaminopyridine, and N-methylimidazole as catalysts. The absolute rates of the catalyzed hydrolysis decreased with increasing acetonitrile content (decreasing solvent polarity), but the catalytic efficiency of N-methylimidazole and 4-dimethylaminopyridine relative to pyridine increased as the solvent polarity decreased. The relative catalytic rates for the cinnamoylation of n-propanol in acetonitrile were 1:259:16,000 for pyridine, N-methylimidazole, and 4-dimethylaminopyridine, respectively.
D002384:Catalysis; D002934:Cinnamates; D006868:Hydrolysis; D007093:Imidazoles; D007700:Kinetics; D011725:Pyridines
D002934:Cinnamates; D007093:Imidazoles; D011725:Pyridines; C031613:cinnamic anhydride