NUCLEOPHILIC AROMATIC-SUBSTITUTION REACTIONS ON 4,5-DICYANO-2-FLUORO-1-METHYLIMIDAZOLE - SYNTHESES AND PROPERTIES OF 4,5-DICYANO-1,3-DIMETHYL-2-IMIDAZOLONE AND ITS PSEUDOOXOCARBON DERIVATIVES

Nucleophilic aromatic substitution (SNAr) reactions of 4, 5-dicyano-2- fluoro-1-methyl-imidazole using disodium cyanamide or disodium malonon itrile followed by methylation using dimethyl sulfate gave the 2-cyani mino and 2-dicyanomethylene pseudooxocarbon derivatives 4 and 6. The o xocarbon analog of 4 and 6, namely 4,5-dicyano-1, 3-dimethyl-2-imidazo lone (7), was synthesized by dimethylation of 4,5-dicyano-2-imidazolon e which, in turn was synthesized from diaminomaleonitrile (DAMN) and t riphosgene. These compounds belong to the class of oxo and pseudooxoca rbon compounds. Thermogravimetric analysis of 6 shows a 30 wt.% loss w hich might suggest the loss of the dicyanomethylene group. The fluores cence spectra of these compounds show strong emissions in the order, 6 (475 nm) < 4 (400 nm) < 7 (345 nm). Cyclic voltammetry of these compo unds in CH3CN shows irreversible cyclic voltammograms around -2.0 volt s vs. Ag/Ag+. Compound 6 forms long crystals of weak, red-colored char ge transfer complexes with tetrathiafulvalene.