144396-06-5Relevant articles and documents
Synthesis, fragmentations and rearrangements of 3-(1-haloalkyl) oxaziridines
De Kimpe, Norbert,De Corte, Bart
, p. 7345 - 7362 (2007/10/02)
A variety of new 3-(1-haloalkyl)oxaziridines was synthesized by oxidation of α-chloro-, α-bromo-, α,α-dichloro-, α,α-dibromo- and α,α,α-trichloroaldimines with meta-chloroperbenzoic acid. Attempts to induce dehydrohalogenation into the elusive methyleneoxaziridines were unsuccessful. However, presumptive evidence is presented that 2-t-butyl-3-(trichloromethyl)oxaziridine is dehydrochlorinated into a transient methyleneoxaziridine, which underwent valence isomerization into an intermediate iminooxirane, the latter being fragmented into t-butyl isocyanide. Various types of reactions of the title compounds are reported. Among others, 2-alkyl-3-(1-chloro-1-methyl) ethyloxaziridines rearranged with methyllithium into 2-(N-alkyl)aminoisobutyraldehydes.
