An oxaziridine is an organic molecule that features a three @-@ membered heterocycle containing oxygen , nitrogen , and carbon . In their largest application , oxazidines are intermediates in the industrial production of hydrazine . Oxaziridine derivatives are also used as specialized reagents in organic chemistry for a variety of oxidations , including alpha hydroxylation of enolates , epoxidation and aziridination of olefins , and other heteroatom transfer reactions . Oxaziridines also serve as precursors to amides and participate in [ 3 + 2 ] cycloadditions with various heterocumulenes to form substituted five @-@ membered heterocycles . Chiral oxaziridine derivatives effect asymmetric oxygen transfer to prochiral enolates as well as other substrates . Some oxaziridines also have the property of a high barrier to inversion of the nitrogen , allowing for the possibility of chirality at the nitrogen center .