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Investigation of the phenylation of methyl-quinolines using tritium-labeled nucleogenic phenyl cations

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Natural Sciences Institute, Perm State University, 4 Genkel St., Perm, 614990, Russia

    N. E. Shchepina & G. A. Alexandrova

  2. Saint Petersburg State University, 7/9 Universitetskaya Nab., 199034, Saint Petersburg, Russia

    V. V. Avrorin

  3. M. V. Lomonosov Moscow State University, 1, Build. 3, Leninskie Gory, Moscow, 119991, Russia

    G. A. Badun

  4. “Technolog Co. Ltd”, 2/157 Mendeleeva St., Pereslavl-Zalessky, 152025, Russia

    I. I. Boiko

  5. Perm State National Research University, 15 Bukirev St., Perm, 614990, Russia

    S. N. Shurov

Authors
  1. N. E. Shchepina
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  2. V. V. Avrorin
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  3. G. A. Alexandrova
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  4. G. A. Badun
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  5. I. I. Boiko
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  6. S. N. Shurov
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Correspondence to N. E. Shchepina.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 461-467, March, 2013.

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Shchepina, N.E., Avrorin, V.V., Alexandrova, G.A. et al. Investigation of the phenylation of methyl-quinolines using tritium-labeled nucleogenic phenyl cations. Chem Heterocycl Comp 49, 428–434 (2013). https://doi.org/10.1007/s10593-013-1264-7

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  • DOI: https://doi.org/10.1007/s10593-013-1264-7

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