Imidazol‐2‐ylidene Reactivity towards Cyanocarbons

Abstract

Abstract The interaction of electron rich imidazol‐2‐ylidenes with electron poor cyanocarbons is reported. Contrary to previous reports of electron transfer products from imidazol‐2‐ylidenes and tetracyanoethylene, a number of ring forming cyanocarbon ring structures are isolated and characterized. Cyanation of the imidazole ring was explored by the addition of cyanogen chloride to imidazol‐2‐ylidenes. Backbone cyanation often occurs when hydrogen atoms are in the C‐4/5 positions. When tetrasubstituted imidazol‐2‐ylidenes are employed, 2‐cyanoimidazolium halide salts can be isolated. These salts maintain an electrophilic cyano group and are precursors to thermally stable high nitrogen content imidazolium tetrazolides.