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

Reactions of N-(Perfluorophenyl)carbonimidoyl Dichloride with Aromatic Acids and Their Derivatives in the Presence of AlCl3. Formation of 2-(Perfluorophenyl)isoindoline-1,3-dione and Its Derivatives

“…benzoyl cation is intermediately formed and taking into consideration the already mentioned [3,4] This scheme is corroborated by transformation into reaction products IIIa and IV of independently synthesized 3,3-dichloro-2-(perfluorophenyl)isoindolin-1-one (X). The synthesis of substituted isoindolin-1-one X was performed by heating cyclic compound IIIa with PCl 5 (Scheme 3).…”

“…Reactions with benzane and alkyl benzenes gave rise to imidoyl chlorides and azomethines [1], and with fluorinated benzenes depending on the number of fluorine atoms in the benzene ring the process afforded imidoyl chlorides, azomethines, or polyfluorinated derivatives of 1,2,3,4-tetrahydroquinazoline-2,4-dione [2]. The reaction at the multiple carbonnitrogen bond in the aromatic imidoyl chlorides or nitriles furnished 5-or 6membered heterocyclic derivatives [4]. The reaction at the multiple carbonnitrogen bond in the aromatic imidoyl chlorides or nitriles furnished 5-or 6membered heterocyclic derivatives [4].…”

Polyfluoroaromatic compounds with a NCClR group—a reactive type of polyfluoroarene

“…The interaction of N-pentafluorophenyltrichloroacetimidoyl chloride (76) with pentafluoroaniline (1) in the presence of AlCl 3 gives bis(pentafluorophenyl)-trichloroacetamidine [74].…”

“…For polyfluoroaromatic imidoyl chlorides, it was also found that their reactions with compounds containing a nitrogen-carbon multiple bond probably involve formation of an intermediate of the nitrilium cation type. These are cycloaddition type reactions leading to five-and six-membered N-heterocyclic systems [74]. Thus, compound 10 or N-(4-methyl-2,3,5,6-tetrafluorophenyl)carbonimidoyl dichloride (35) react with trichloroacetimidoyl chloride 76, giving 2-imidazolidones 119, which on heating with AlCl 3 are transformed into 2-imidazolone 120.…”

“…The appropriate triazin-2-ones 124 are obtained as the major products in the reaction of 10 or N-(2-H-3,4,5,6-tetrafluorophenyl)carbonimidoyl dichloride (39) with benzonitrile at 150 8C and higher temperature (Scheme 22) [20,74].…”