Phenyl acetate, methoxyaminolysis

Scheme 11.14 Bifunctional acid-base catalysis of the proton switch which traps the zwitterionic intermediate in methoxyaminolysis of phenyl acetate.

Push-pull acid-base catalysis has been proposed to account for the proton switch mechanism which occurs in the methoxyaminolysis of phenyl acetate (Scheme 11.14) where a bifunctional catalyst traps the zwitterionic intermediate. A requirement of efficient bi-functional catalysis is that the reaction should proceed through an unstable intermediate which has p values permitting conversion to the stable intermediate or product by two proton transfers after encounter with the bifunctional catalyst the proton transfer with monofunctional catalysts should also be weak. 

Cox, M.M., Jencks, W.P. Catalysis of the methoxyaminolysis of phenyl acetate by a preassociation mechanism with a solvent isotope effect maximum. J. Am. Chem. Soc. 1981,103(3), 572-580. 

---

See also in sourсe #XX -- [ ]

---