Interaction of polyfluoroaromatic imidoyl chloride derivatives with compounds containing nitrogen–carbon multiple bonds in the presence of AlCl3

Interactions of polyfluoroaromatic imidoyl chloride derivatives with compounds containing nitrogen–carbon multiple bond in the presence of AlCl3 proceed as a cycloaddition type process and lead to five- or six-membered N-containing ring systems. N-(p-R–tetrafluorophenyl)carbonimidoyl dichlorides (R = F, CH3) react with N-pentafluorophenyltrichloroacetimidoyl chloride and AlCl3 to give in good yields 1-(p-R–tetrafluorophenyl)-3-pentafluorophenyl-4,4,5,5-tetrachloro-2-imidazolidones. N-Pentafluorophenyltrichloroacetimidoyl chloride “dimerizes” by heating with AlCl3 to 1,3-bis(pentafluorophenyl)-4,5-dichloro-2-imidazolone. This compound was also obtained from 1,3-bis(pentafluorophenyl)-4,4,5,5-tetrachloro-2-imidazolidone under the action of AlCl3. Heating of 1,3-bis(pentafluorophenyl)-4,4,5,5-tetrachloro-2-imidazolidone with AlCl3 in toluene leads to 1,3-bis(pentafluorophenyl)-4,5-dichloro-2-imidazolone and its 5-tolyl derivatives as a result of a reaction with toluene. Interaction of N-pentafluorophenylcarbonimidoyl dichloride with benzonitrile and AlCl3 leads to 1-pentafluorophenyl-4,6-diphenyl-1,3,5-triazine-2-one along with N-pentafluorophenyl-N′-benzoylurea and an N-pentafluorophenylurea complex with benzamide.