127776-13-0Relevant academic research and scientific papers
Reductive activation of arenes 22. Reactions of the terephthalonitrile radical anion and dianion with α,ω-dibromoalkanes. New evidence for the charge transfer complex as a key intermediate in the reactions of the dianion
Panteleeva,Lukyanova,Pokrovsky,Shteingarts
, p. 1110 - 1118 (2008/09/18)
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.
