Synthesis and reactivity of α-halomethyl ketimines

Article abstract of DOI:10.1016/S0040-4020(01)88533-1

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.