KINETIC-STUDIES OF THE N-ALKYLATION OF SECONDARY-AMINES WITH 1,2-DICHLOROETHANE

The reactions of 1,2-dichloroethane with 2-(ethylamino)ethanol or diet hylamine have been investigated in several solvents from 51 to 80-degr ees-C. A reaction mechanism has been proposed where 1,2-dichloroethane reacts with the secondary amines in both bimolecular substitution (SN 2) and elimination (E2) reactions; the substitution product is rapidl y converted in an aziridinium ion and undergoes a consecutive reaction with the starting amine to give a tetrasubstituted ethylenediamine. T he rate constants as well as the activation energies of these reaction s have been determined. (C) 1994 John Wiley & Sons, Inc.