Gas phase identification of the elusive oxaziridine (cyclo-H2CONH) - an optically active molecule
Santosh K Singh1, Jesse La Jeunesse, Cheng Zhu
1Department of Chemistry, University of Hawaii, 2545 McCarthy Mall, Honolulu, HI 96822, USA. ralfk@hawaii.edu.
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.
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