KINETIC-STUDIES OF THE REACTIONS OF 2-DIETHYLAMINOETHYLCHLORIDE WITH NUCLEOPHILIC-REAGENTS IN N,N-DIMETHYLFORMAMIDE

The kinetics of the reactions of 2-diethylaminoethylchloride with nucl eophilic reagents have been studied in N, N-dimethylformamide from 33 to 80 degrees C. An ethyleneimmonium ion is easily formed from 2-dieth ylaminoethylchloride by the participation of the neighbouring nitrogen atom. This ion is rather stable in N,N-dimethylformamide solution and is in equilibrium with 2-diethylaminoethylchloride. However, it react s very rapidly with various nucleophilic reagents such as 8-benzyltheo phylline and 2-(ethylamino)ethanol. The formation of the ethyleneimmon ium ion is slower than the nucleophilic substitution reaction. The equ ilibrium constant and the rate constant of the formation of the ethyle neimmonium ion, as well as the rate constants of the nucleophilic subs titution reactions, have been determined.