Imines dimethyldioxirane

Oxidation of A-alkyl imines with dimethyldioxirane (DMD) in a solution of dichloromethane-acetone gives nitrones without the apparent formation of oxaziridines (13). Under the conditions of phase transfer, imines can be oxidized into nitrones upon treatment with permanganate ion MnC>4 (19). 

The formal addition of an oxygen atom across the carbonyl group gives rise to dioxiranes (equation 33). In practice, this reaction is effected with Oxone, and dimethyldioxirane (30) and other dioxiranes have been generated in solutions of their parent ketones. Dioxirane (30) has been implicated in oxidations of alkenes, sulfides and imines. The formal addition of nitrogen across a carbon-oxygen double bond to afford oxaziridines has been reviewed (equation 34). - There are also many methods available for the indirect conversion of carbonyl compounds to aziridines > and thiiranes using multi-step conversions. 

The addition of BF3-OEt2 to an a-phosphorylated imine results in the 1,3-transfer of a diphenylphosphinoyl group, with resultant migration of the C-N=C triad. This method is less destructive than the thermal rearrangement. The decomposition of dimethyldioxirane in acetone to methyl acetate is accelerated with BF3 OEt2, but acetol is also formed. Propene oxide undergoes polymerization with BF3-OEt2 in most solvents, but isomerizes to propionaldehyde and acetone in dioxane. ... 

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