Chemistry of Heterocyclic Compounds

, Volume 49, Issue 11, pp 1640–1652 | Cite as

Electron Transfer Reactions in the Chemistry of Di- and Tetrahydropyridines

  • B. TurovskaEmail author
  • I. Goba
  • A. Lielpetere
  • I. Turovskis
  • V. Lusis
  • Dz. Muceniece
  • J. Stradiņš

The mechanism of electrochemical oxidation of 1,2,3,4-tetrahydropyridines in acetonitrile has been studied. A single reversible one-electron oxidation is registered in the accessible voltage range. The reversibility of the process is sensitive to the traces of oxygen in solution. The electrochemically generated radical cation of tetrahydropyridine may act as a mediator in an indirect oxidation of dihydropyridines if the difference in oxidation potentials between two compounds is less than 200 mV. During the indirect oxidation of 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester to 3,5-bis(ethoxycarbonyl)-2,4,6-trimethylpyridinium perchlorate, some of the starting tetrahydropyridine is protonated, thus making it anodically inactive.


1,4-dihydropyridine 1,2,3,4-tetrahydropyridine charge transfer mediator electrooxidation indirect oxidation 


The work was financially supported by the Latvian Council of Science (grant 09-1558) and by the European Regional Development Fund (ERDF) project No. 2DP/

The authors thank Dr. Chem. E. Liepinsh for NMR analysis of epimers on the Bruker DMX-600 spectrometer and Dr. Chem. S. Grinberga for GC-MS analysis.


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • B. Turovska
    • 1
    Email author
  • I. Goba
    • 1
  • A. Lielpetere
    • 1
  • I. Turovskis
    • 1
  • V. Lusis
    • 1
  • Dz. Muceniece
    • 1
  • J. Stradiņš
    • 1
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia

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