Reactions of N-polyfluorophenylcarbonimidoyl dichlorides with primary and secondary amines. Kinetics and mechanism. Synthesis of polyfluorinated carbodiimides, chloroformamidines, guamidines and benzimidazoles.

摘要: Abstract The reaction of N-polyfluorophenylcarbonimidoyl dichlorides with primary and secondary aliphatic aromatic amines have been studied. With amines, the reactions led to carbodiimides or guanidines, depending on amount amine. obtained reacted form guanidines. produced only triarylguanidines. N-Pentafluorophenyllcarbonimidoyl dichloride (I) tetrafluoro-o-phenylene diamine give 2-pentafluoroanilino-4,5,6,7-tetrafluorobenzimidazole. Polyfluorinated benzimidazole derivatives were also by thermolysis polyfluorinated Heating N 1 ,N 2 3 -tris(pentafluorophenyl)guanidine K CO in dimethylformamide 1,2,3,4,7,8,9,10-octafluoro-5-pentafluorophenyl-5H-benzimidazol[1,2-a]benzimidazole. N-Polyfluorophenylcarbonimidoyl various already at room temperature giving N-polyfluorophenylchloroformamidines high yields. Elevated prolonged time formation N-polyfluorophenylguanidines. Kinetics mechanism acetonitrile 25°C found proceed a bimolecular nucleophilic addition-elimination via tetrahedral intermediate. Possible reasons different products above transformation are discussed terms this mechanism.