15679-00-2Relevant articles and documents
Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides
Adhikari, Arijit A.,Suzuki, Tamie,Gilbert, Reesheda T.,Linaburg, Matthew R.,Chisholm, John D.
, p. 3982 - 3989 (2017/04/11)
The rearrangement of allylic trichloroacetimidates is a well-known transformation, but the corresponding rearrangement of benzylic trichloroacetimidates has not been explored as a method for the synthesis of benzylic amines. Conditions that provide the tr
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.