Cyanophenylation of Aromatic Nitriles by Terephthalonitrile Dianion: Is the Charge??Transfer Complex a Key Intermediate?

EV Panteleeva, LN Shchegoleva…

Index: Panteleeva, Elena V.; Shchegoleva, Lyudmila N.; Vysotsky, Viktor P.; Pokrovsky, Leonid M.; Shteingarts, Vitalij D. European Journal of Organic Chemistry, 2005 , # 12 p. 2558 - 2565

Full Text: HTML

Citation Number: 9

Abstract

Abstract The interaction of terephthalonitrile (1) dianion (1 2–) with benzonitrile (2) or m- tolunitrile (3) provides 4, 4'-dicyanobiphenyl (4) or 4, 4'-dicyano-2-methylbiphenyl (5), respectively. This result shows that dianion 1 2–serves as a reagent for p-cyanophenylation of aromatic nitriles. Based on experimental data, such as the chemical trapping of the 4, 4'- dicyanobiphenyl precursor 4-cyano-1-(p-cyanophenyl) cyclohexa-2, 5-dienyl anion (7) ...