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Synthesis, fragmentations and rearrangements of 3-(1-haloalkyl)oxaziridines

(1992) TETRAHEDRON. 48(35). p.7345-7362
Author
Organization
Abstract
A variety of new 3-(1-haloalkyl)oxaziridines was synthesized by oxidation of alpha-chloro-, alpha-bromo-, alpha,alpha-dichloro-, alpha,alpha-dibromo-, and alpha,alpha,alpha-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 tide compounds are reported. Among others, 2-alkyl-3-(1-chloro-1-methyl)ethyloxaziridines rearranged with methyllithium into 2-(N-alkyl)aminoisobutyraldehydes.
Keywords
ALPHA-HALOGENATED IMINES, METHYLENECYCLOPROPANE ANALOGS, ENANTIOSELECTIVE SYNTHESIS, PHOTOCHEMICAL FORMATION, OXAZIRIDINES, CHEMISTRY, MECHANISM, HETEROATOMS, ELIMINATION, REACTIVITY

Citation

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Chicago
De Kimpe, Norbert, and Bart De Corte. 1992. “Synthesis, Fragmentations and Rearrangements of 3-(1-haloalkyl)oxaziridines.” Tetrahedron 48 (35): 7345–7362.
APA
De Kimpe, N., & De Corte, B. (1992). Synthesis, fragmentations and rearrangements of 3-(1-haloalkyl)oxaziridines. TETRAHEDRON, 48(35), 7345–7362.
Vancouver
1.
De Kimpe N, De Corte B. Synthesis, fragmentations and rearrangements of 3-(1-haloalkyl)oxaziridines. TETRAHEDRON. 1992;48(35):7345–62.
MLA
De Kimpe, Norbert, and Bart De Corte. “Synthesis, Fragmentations and Rearrangements of 3-(1-haloalkyl)oxaziridines.” TETRAHEDRON 48.35 (1992): 7345–7362. Print.
@article{206716,
  abstract     = {A variety of new 3-(1-haloalkyl)oxaziridines was synthesized by oxidation of alpha-chloro-, alpha-bromo-, alpha,alpha-dichloro-, alpha,alpha-dibromo-, and alpha,alpha,alpha-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 tide compounds are reported. Among others, 2-alkyl-3-(1-chloro-1-methyl)ethyloxaziridines rearranged with methyllithium into 2-(N-alkyl)aminoisobutyraldehydes.},
  author       = {De Kimpe, Norbert and De Corte, Bart},
  issn         = {0040-4020},
  journal      = {TETRAHEDRON},
  keyword      = {ALPHA-HALOGENATED IMINES,METHYLENECYCLOPROPANE ANALOGS,ENANTIOSELECTIVE SYNTHESIS,PHOTOCHEMICAL FORMATION,OXAZIRIDINES,CHEMISTRY,MECHANISM,HETEROATOMS,ELIMINATION,REACTIVITY},
  language     = {eng},
  number       = {35},
  pages        = {7345--7362},
  title        = {Synthesis, fragmentations and rearrangements of 3-(1-haloalkyl)oxaziridines},
  url          = {http://dx.doi.org/10.1016/S0040-4020(01)88271-5},
  volume       = {48},
  year         = {1992},
}

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