E. Panteleeva, M. Y. Lukyanova, L. M. Pokrovsky
Jun 1, 2007
Citations
0
Influential Citations
3
Citations
Journal
Russian Chemical Bulletin
Abstract
The major products of reactions of the terephthalonitrile radical anion with α,ω-dibromoalkanes Br(CH2)nBr (n = 3–5) were 4-(ω-bromoalkyl)benzonitriles. Analogous reactions of the terephthalonitrile dianion mainly yielded α,ω-bis(4-cyanophenyl)alkanes. Both transformations are convenient one-step routes to otherwise not easily accessible compounds that are valuable as versatile building blocks. The results of alkylation allow one to suggest that reactions of the dianion with intermediate 4-(ω-bromoalkyl)benzonitriles proceed more rapidly than those with the starting α,ω-dibromoalkanes. This was confirmed by competitive reactions of the dianion with 4-(ω-bromoalkyl)benzonitriles and the corresponding alkyl bromides. To explain such a ratio of the reaction rates, a mechanism was proposed for the reaction of the dianion with 4-(ω-bromoalkyl)benzonitriles. According to this mechanism, a charge transfer complex is a key reaction intermediate.