Interaction of polyfluoroaromatic imidoyl chloride derivatives with compounds containing nitrogen–carbon multiple bonds in the presence of AlCl 3

Abstract

Interactions of polyfluoroaromatic imidoyl chloride derivatives with compounds containing nitrogen–carbon multiple bond in the presence of AlCl 3 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, CH 3) react with N-pentafluorophenyltrichloroacetimidoyl chloride and AlCl 3 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 AlCl 3 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 AlCl 3. Heating of 1,3-bis(pentafluorophenyl)-4,4,5,5-tetrachloro-2-imidazolidone with AlCl 3 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 AlCl 3 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.