The photolysis of n - chloroacetamide

Abstract

The mechanisms by which halogenoamines such as N-chloroacetanilide undergo rearrangement, have been the subject of a large volume of work ever since Bender Ber., 1886, 192, 272 studied the displacement of the aminic hydrogen in acetanilide by chlorine. A typical example is the conversion of N-chloroacetanilide into a fixture of o- and p-chloroacetanilide, in the presence of hydrochloric acid, and usually in hydroxylic solvents such as acetic acid, or water, or aqueous acetic acid. On the other hand, the photolysis of this chloroamine type of compound in general, has received comparatively little treatment, although it is well known that they decompose in sunlight. The earliest investigations were mainly confined to the conversion of N-chloroscetanilide into a mixture of o- and 2- chloroacetanilide, in the presence of hydrochloric acid.