62134-57-0Relevant academic research and scientific papers
Rearrangement of 4-(1-haloalkyl)- and 4-(2-haloalkyl)-2-azetidinones into methyl ω-alkylaminopentenoates via transient aziridines and azetidines
Dejaegher, Yves,De Kimpe, Norbert
, p. 5974 - 5985 (2004)
The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2- azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and α-haloimines or β-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkyl-amino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.
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.
