3,3-Pentamethylene oxaziridine

There are only few reactions known introducing substituents to the H-bearing nitrogen of oxaziridines. (V-Alkylation of l-oxa-2-azaspiro[2.5]octane (3,3-pentamethylene-oxaziridine 52) with r-butyl chloride to give (53) was carried out for structure proof of (52). This reaction is of no preparative importance, since N-alkylated oxaziridines are easily obtained by ring synthesis. 

Earlier, irradiation of 3,3-pentamethylene oxaziridine 67 was reported to give cyclohexanol and n-caproamide, via an excited triplet state, and e-caprolactam, dicyclohexylideneazine, and cyclohexanone via a singlet excited state. The lowest triplet energy of 67 was estimated to be 60kcal/mol. ... 

A potentially important industrial application of this reaction involves the thermal rearrangement of 3,3-pentamethylene-oxaziridine 67 to e-caprolactam, a reaction that is strongly catalyzed by transition-metal ions. ... 

Cyclohexanone is also the starting material for process 8 (Figure 2.11). This process does not appear to be commercially practiced. It is characterized by the formation of cyclohexanoni-soxim (3,3 -pentamethylene oxaziridine) upon treatment of cyclohexanone in a toluene solution with ammonia and sodium hypochloride [124] ... 

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