Spontaneous Oxygenation of Siloxy-N-silylketenimines to α-Ketoamides

Siloxy-N-silylketenimines generated in situ from O-silyl cyanohydrins were converted to α-ketoamides by brief exposure to air or oxygen. Oxidation under extremely mild conditions can be explained by assuming the intermediacy of a 3-imino-1,2-dioxetane derivative generated via triplet–singlet intersystem crossing after the reaction of siloxy-N-silylketenimines with triplet oxygen.