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

被引:5
作者
Petrova, TD [1 ]
Platonov, VE [1 ]
Kolesnikova, IV [1 ]
Ribalova, TV [1 ]
Bagryanskaya, IY [1 ]
Gatilov, YV [1 ]
机构
[1] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia
关键词
polyfluoroaromatic imidoyl chloride derivatives; 2-imidazolidones; 2-imidazolones; 1-pentafluorophenyl-4,6-diphenyl-1,3,5-triazine-2-one; AlCl3;
D O I
10.1016/S0022-1139(99)00257-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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-imidazolone. N-Pentafluorophenyltrichloroacetimidoyl chloride "dimerizes" by heating with AlCl3 to 1,3-bis(pentafluorophenyl)-4,5-dichloro-2 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. (C) 2000 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:63 / 73
页数:11
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