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Synthesis and reactivity of alpha-halomethyl ketimines

(1992) TETRAHEDRON. 48(13). p.2739-2760
Author
Organization
Abstract
The synthesis of N-(1-halo-2-alkylidene)amines, i.e. alpha-halomethyl ketimines, is described for the first time, utilizing the TiCl4-induced condensation of alpha-halomethyl ketones with primary amines. The reactivity of these new alpha-halomethyl ketimines was studied with respect to nucleophiles such as iodide, cyanide, alcohols, alkoxides, amines and thiolates. Alpha-halomethyl ketimines are powerful ambident electrophiles which underwent a variety of reactions leading to functionalized imines and heterocycles.
Keywords
IMINES, INTRAMOLECULAR-CYCLOADDITION, CHEMISTRY

Citation

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Chicago
De Kimpe, Norbert, W Decock, and Christian Stevens. 1992. “Synthesis and Reactivity of Alpha-halomethyl Ketimines.” Tetrahedron 48 (13): 2739–2760.
APA
De Kimpe, N., Decock, W., & Stevens, C. (1992). Synthesis and reactivity of alpha-halomethyl ketimines. TETRAHEDRON, 48(13), 2739–2760.
Vancouver
1.
De Kimpe N, Decock W, Stevens C. Synthesis and reactivity of alpha-halomethyl ketimines. TETRAHEDRON. 1992;48(13):2739–60.
MLA
De Kimpe, Norbert, W Decock, and Christian Stevens. “Synthesis and Reactivity of Alpha-halomethyl Ketimines.” TETRAHEDRON 48.13 (1992): 2739–2760. Print.
@article{205073,
  abstract     = {The synthesis of N-(1-halo-2-alkylidene)amines, i.e. alpha-halomethyl ketimines, is described for the first time, utilizing the TiCl4-induced condensation of alpha-halomethyl ketones with primary amines. The reactivity of these new alpha-halomethyl ketimines was studied with respect to nucleophiles such as iodide, cyanide, alcohols, alkoxides, amines and thiolates. Alpha-halomethyl ketimines are powerful ambident electrophiles which underwent a variety of reactions leading to functionalized imines and heterocycles.},
  author       = {De Kimpe, Norbert and Decock, W and Stevens, Christian},
  issn         = {0040-4020},
  journal      = {TETRAHEDRON},
  keyword      = {IMINES,INTRAMOLECULAR-CYCLOADDITION,CHEMISTRY},
  language     = {eng},
  number       = {13},
  pages        = {2739--2760},
  title        = {Synthesis and reactivity of alpha-halomethyl ketimines},
  volume       = {48},
  year         = {1992},
}