Gas phase identification of the elusive oxaziridine (cyclo-H2CONH) – an optically active molecule

Abstract

The hitherto elusive oxaziridine molecule (cyclo-H₂CONH) – an optically active, high energy isomer of nitrosomethane (CH₃NO) – is prepared in processed methane–nitrogen monoxide ices and detected upon sublimation in the gas phase. Electronic structure calculations reveal likely routes via addition of carbene (CH₂) to the nitrogen–oxygen double bond of nitrosyl hydride (HNO). Our findings provide a fundamental framework to explore the preparation and stability of racemic oxaziridines exploited in chiral substrate-controlled diastereoselective preparation such as Sharpless asymmetric epoxidation, thus advancing our fundamental understanding of the preparation and chemical bonding of strained rings in small organic molecules.