A new reaction pathway in the ester aminolysis catalyzed by glymes and crown ethers

J Org Chem. 2006 May 26;71(11):4280-5. doi: 10.1021/jo060389u.

Abstract

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.