Synthesis of dicationic hetarylmethylimidazolium salts via the reaction of N, N′-diaryl-4-chloromethylimidazolium chlorides with N-heterocycles

The reaction between N, N′-diaryl-4-chloromethylimidazolium chlorides and N-nucleophiles, viz. various azoles and azines, which proceeds via nucleophilic substitution of the chlorine atom in the chloromethyl group and leads to new dicationic 4-hetarylmethylimidazolium salts, was investigated. This reaction is reversible, whereas the yield of product of the nucleophilic substitution depends significantly on the structure of heterocyclic nucleophile and the nature of used solvent. A series of new dicationic 4-hetarylmethylimidazolium salts was obtained, and they are of interest as promising components of ionic liquids and precursors of N-heterocyclic carbenes.