INVESTIGATION OF THE PHENYLATION OF METHYLQUINOLINES USING TRITIUM-LABELED NUCLEOGENIC PHENYL CATIONS

Abstract

The phenylation of methylquinolines by nucleogenic phenyl cations was studied. This reaction led to a product mixture through electrophilic addition and electrophilic substitution, with composition depending on the methyl substituent position. In the case of 4-methylquinoline, the electron-donating methyl group in the para position markedly increased the yield of N‑phenylquinolinium derivative, while the low yield of the quinolinium salt in the case of 8‑methylquinoline was due to the  two factors – low basicity of the nitrogen atom in comparison to 4-methylquinoline and steric hindrance by the methyl group, which led to predominant electrophilic substitution.

Authors: N. E. Shchepina, V. V. Avrorin, G. A. Alexandrova, G. A. Badun, I. I. Boiko, and S. N. Shurov

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (3), pp 428-434

http://link.springer.com/article/10.1007/s10593-013-1264-7