Photochemistry of chloroacetanilide derivatives: rearrangement, cyclization, and solvolysis

Abstract

N-Chloroacetylamines on photolysis in methanol, rearrange to give N-substituted glycine esters and methyl esters. Conditions have been established for the formation of a five-membered lactam system by cyclization. A dual mechanism is shown to be operative in the photolysis of the chloroacetamide function in polar and non-polar solvents, giving solvolytic and hydrogen-abstracted products respectively.