ChemInform Abstract: Superelectrophilic Chemistry of Imidazoles.

Abstract

Imidazole derivatives R 0190Superelectrophilic Chemistry of Imidazoles. -Treatment of imidazole ketones, aldehydes, and alcohols with TfOH results in formation of dicationic species which smoothly react with arenes to afford products like (III), (V), and (VII). Under appropriate conditions, charge migration can be observed yielding derivatives such as (VIII). In some cases intramolecular cyclization is possible to give fused imidazoles. N-Acylated imidazoles smoothly undergo acyl transfer reaction in the presence of TfOH. -(SHEETS, M. R.; LI, A.; BOWER, E. A.; WEIGEL, A. R.; ABBOTT, M. P.; GALLO, R. M.; MITTON, A. A.; KLUMPP*, D. A.; J.