Tetrahedron p. 2739 - 2760 (1992)
Update date:2022-08-04
Topics:
De Kimpe
De Cock
Stevens
The synthesis of N-(1-halo-2-alkylidene)amines, i.e. α-halomethyl ketimines, is described for the first time, utilizing the TiCl4-induced condensation of α-halomethyl ketones with primary amines. The reactivity of these new α-halomethylketimines was studied with respect to nucleophiles such as iodide, cyanide, alcohols, alkoxides, amines and thiolates. α-Halomethyl ketimines are powerful ambident electrophiles which underwent a variety of reactions leading to functionalized imines and heterocycles.
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Doi:10.1016/S0040-4039(00)85100-X
(1986)Doi:10.1021/ja01308a049
(1935)Doi:10.1016/j.molcatb.2013.06.016
(2013)Doi:10.1021/om00043a076
(1992)Doi:10.1039/c2dt32487c
(2013)Doi:10.1021/acs.orglett.0c02378
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