Autoxidation of N-alkylamides. Part I. N-Acylamides as oxidation products

Abstract

Products of the thermal and photosensitised autoxidation of N-alkyl- and NN-dialkyl-amides have been identified. N-n-Alkylamides yield principally N-acylamides, primary amides, and N-formylamides, as a result of initial abstraction of a hydrogen atom from the carbon adjacent to nitrogen. Formation of N-formylamides, and of N-acylamides from N-s-alkylamides, involves C₍₁₎–C₍₂₎ bond scission in an N-alkyl group. Oxidation of NN-dialkylamides follows a similar pattern. Gas–liquid-chromatographic retention data are presented for 89 amides.