Chemistry of Heterocyclic Compounds

, Volume 46, Issue 5, pp 547–552

New method for the synthesis of difficultly available sterically hindered tritium-labeled pyridinium derivatives

  • N. E. Shchepina
  • V. V. Avrorin
  • G. A. Badun
  • V. M. Fedoseev
  • S. B. Lewis
Article

DOI: 10.1007/s10593-010-0544-8

Cite this article as:
Shchepina, N.E., Avrorin, V.V., Badun, G.A. et al. Chem Heterocycl Comp (2010) 46: 547. doi:10.1007/s10593-010-0544-8

Direct phenylation of the nitrogen atom in pyridines was noted in a study of the ion-molecule reactions of free nucleogenic phenyl cations generated by β-decay of tritium in labeled benzene. A one-step synthesis of unreported biologically active tritium-labeled N-phenyl-2,6-lutidinium and 2,4,6-collidi-nium salts. Steric factors, which significantly reduce the yield in the case of sym-collidine, play a major role in the direct phenylation of nitrogen.

Keywords

nucleogenic phenyl cations. N-phenyl-2,6-lutidinium and N-phenyl-2,4,6-collidinium salts tritium direct phenylation of pyridine nitrogen atom 

Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • N. E. Shchepina
    • 1
  • V. V. Avrorin
    • 2
  • G. A. Badun
    • 3
  • V. M. Fedoseev
    • 3
  • S. B. Lewis
    • 4
  1. 1.Natural Sciences InstitutePerm State UniversityPermRussia
  2. 2.St. Petersburg State UniversitySt. PetersburgRussia
  3. 3.M. V. Lomonosov Moscow State UniversityMoscowRussia
  4. 4.James Madison UniversityHarrisonburgUSA

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