Polyfluorinated Oxaziridines:  Synthesis and Reactivity

Oxaziridines are three-membered heterocyclic compounds containing oxygen, nitrogen, and carbon. They were first described in mid-1950s,1-3 but the first perfluorinated example was reported in mid-1970s.4 Some scattered papers in the 1980s have provided evidence of the unusual reactivity and unique properties of these perfluorinated heterocycles. It is only in the last five years, however, that a strong focus on the area allowed the unique properties of polyfluorinated oxaziridines to be recognized. For instance, perfluorinated oxaziridines as oxidants are much closer to dioxiranes than to hydrocarbon oxaziridines. This is a consequence of the dramatic effect of electon-withdrawing perfluoroalkyl groups. While the chemistry of hydrocarbon oxaziridines has been reviewed in several papers,5-10 the current work is the first attempt to provide a comprehensive survey of the synthesis, physical properties, and reactions of poly- and perfluorinated oxaziridines.