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Electrolytic oxidation of C4-nitrofuryl 1,4-dihydropyridines in nonaqueous medium

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2007
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Núñez Vergara, Luis
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Electrolytic oxidation of C4-nitrofuryl 1,4-dihydropyridines in nonaqueous medium
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Author
  • Núñez Vergara, Luis;
  • Salazar González, Ricardo Andrés;
  • Navarrete Encina, Patricio;
  • Camargo Grandón, Rodrigo;
  • Yáñez Soto, Claudia;
  • Squella Serrano, Juan;
Abstract
A study of the electrolytic oxidation of three new C-4 nitrofuryl 1,4-dihydropyridines in nonaqueous aprotic medium is presented. Controlled-potential electrolysis (CPE) in dimethylformamide +0.1 M tetrabutyl-ammonium hexafluorophosphate (TBAPF(6)) was followed by UV-visible spectroscopy, high-performance liquid chromatography (HPLC)-photodiode array (PDA), and gas chromatography-Mossbauer spectroscopy (GC-MS) chromatography, and electron spin resonance and electrochemical techniques. Carbon-centered radical intermediates produced in the electrochemical oxidation of C-4 nitrofuryl substituted 1,4dihydropyridines were trapped with N-benzylidene-tert-butylamine-N-oxide (PBN) and their splitting constants were calculated. The neutral pyridine derivatives were identified by GC-MS techniques as final oxidation products. HPLC-PDA and GC-MS chromatographic techniques were used to follow the time-course of CPE of both parent 1,4-DHP derivatives and their respective oxidation products. Also, an overall oxidation mechanism of C-4 nitrofuryl-1,4-DHP derivatives is presented.
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URI: https://repositorio.uchile.cl/handle/2250/120483
ISSN: 0013-4651
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JOURNAL OF THE ELECTROCHEMICAL SOCIETY 154(2):F25-F30
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