Reactions of Ethylenimines. IX. The Mechanisms of Ring Openings of Ethylenimines in Acidic Aqueous Solutions

Abstract

Kinetic measurements and product identifications have been carried out in order to elucidate the mechanisms of several more imine ring openings. Aziridines studied were 2,2-dimethylethylenimine, 2-ethylethylenimine, N-(n-butyl)-ethylenimine and ethylenimine; nucleophiles studied were acetate, bromide, chloride, iodide, thiocyanate and thiosulfate ions, thiourea and water. Hydrolysis rates were studied over a range of temperature and pressure so as to obtain activation parameters. All of the reactions studied have been found to correlate with known mechanistic patterns. The use of linear free energy equations for the evaluation of relative contributions of Sn1 and Sn2 behavior in solvolysis reactions is pointed out. © 1958, American Chemical Society. All rights reserved.