Open Access Open Access  Restricted Access Subscription Access

ELECTRON TRANSFER REACTIONS IN CHEMISTRY OF DI- AND TETRAHYDROPYRIDINES

B. Turovska, I. Goba, A. Lielpetere, I. Turovskis, V. Lusis, Dz. Muceniece, J. Stradins
Cover Image

Abstract


The mechanism of the 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 of tetrahydropyridines 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.

How to Cite
Turovska, B.; Goba, I.; Lielpetere, A.; Turovskis, I.; Lusis, V.; Muceniece, Dz.; Stradiņš, J. Chem. Heterocycl. Compd. 2014, 49, 1640. [Khim. Geterotsikl. Soedin. 2013, 1770.]

For this article in the English edition see DOI 10.1007/s10593-014-1415-5


Keywords


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

Full Text: PDF Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv