Abstract
Chemistry of Cyanogen: Reactions of Diiminosuccinonitrile (DISN) with Sulfenyl Chlorides, Chlorotrimethylsilane and Ring Closure to Trifluoromethyl-Substituted 2H-Imidazoles 4,5-Dicyano-2-hydroxy-2-(trifluoromethyl)-2H-imidazole (1) is easily prepared by treating DISN with trifluoroacetic anhydride. In the presence of 4-(dimethylamino)pyridine, however, the O-acylated derivative 2 is formed in excellent yield, while the reaction of 1 with chlorotrimethylsilane affords the O-silylated product 6. A bi-1,2,5-thiadiazole of the formula S2(CN)4Cl2 (5) is the final reaction product, when DISN is treated with sulfur dichloride in the presence of “naked” chloride ions. On the other hand the non-heterocyclic N-sulfenyl derivative 4 has readily been obtained, when DISN is treated with F3CSCl instead. Finally a procedure is described to convert DISN into the corresponding N-silylated diimine 3.
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