A New Reaction Pathway in the Ester Aminolysis Catalyzed by Glymes and Crown Ethers

Nuno Basilio, Luis García-Río, Juan C. Mejuto, and Moisés Pérez-Lorenzo

J. Org. Chem., 2006, 71, 4280–4285

Butylaminolysis of p-nitrophenyl acetate in chlorobenzene in the presence of different kinds of phase-transfer catalysts (crown ethers and glymes) supports the existence of a reaction pathway exhibiting a first-order dependence on the concentration of the phase transfer catalyst and a second-order dependence on the concentration of butylamine. This novel reaction pathway must be included in the mechanism traditionally accepted for the catalysis by phase-transfer agents of aminolysis reactions in aprotic solvents.