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

The hitherto elusive oxaziridine molecule (cyclo-H 2 CONH) - an optically active, high energy isomer of nitrosomethane (CH 3 NO) - 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 (CH 2 ) 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. First detection of the chiral oxaziridine (cyclo-H 2 CONH) molecule.