The kinetics and mechanisms of additions to olefinic substances. Part XII. Kinetics of addition initiated by chlorine acetate

Abstract

The kinetics of the reactions of electrophilic chlorine acetate with methyl p-nitro-trans-cinnamate in acetic acid and in acetic acid containing various proportions of water, and of the similar reactions of methyl p-chloro-trans-cinnamate, of trans-1-nitro-2-phenylethylene, and of acrylic acid in aqueous acetic acid are described. The results confirm that the principal reagent effective under these conditions is molecular chlorine acetate. Catalysis by added mineral acid, indicating reaction through a protonated species, is found also. The products of the reactions of chlorine acetate and of chlorine with trans-1-nitro-2-phenylethylene are described also.