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Elektronenübertragungsreaktionen, I Produktanalysen der Einelektronen-Oxidation von Olefinen mit Ferriin oder Bleidioxid in wäßriger und methanolischer Lösung/ Electron Transfer Reactions, I Product Analyses of One-Electron Oxidations of Olefins by Ferriin or Lead Dioxide in Aqueous and Methanolic Solutions

Hans-Werner Frühauf, Ernst A. Koerner Von Gustorf
1976 Zeitschrift für Naturforschung. B, A journal of chemical sciences  

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The oxidation of the substituted ethylenes, 2,3-dimethylbutene-2 (1), 2-methylbutene-2 (8), and α-methylstyrene (18), by ferriin or lead dioxide in water and/or methanol has been studied. Product analyses of the reactions, which lead to kinetically controlled product distributions, showed that lead dioxide, just as ferriin, reacts as a one-electron-oxidant. The product distributions, which arise from further reactions of the primary intermediates, i. e. the radical cations formed via
more » ... n transfer, were found to depend on substituents, acidity and solvent. The results are consistent with three separate reaction paths of the radical cation, each of which leads to specific products. The radical cation can either deprotonate, be nucleophilicly attacked by solvent, or lead to dimeric products. The first two possibilities only are observed in the oxidation of 1 and 8, while only the latter two are found in the oxidation of 18.
doi:10.1515/znb-1976-0407 fatcat:ma6twr3cv5axvg6kuqcnpqclvu
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Hans-Werner Frühauf, Ernst A. Koerner Von Gustorf. "Elektronenübertragungsreaktionen, I Produktanalysen der Einelektronen-Oxidation von Olefinen mit Ferriin oder Bleidioxid in wäßriger und methanolischer Lösung/ Electron Transfer Reactions, I Product Analyses of One-Electron Oxidations of Olefins by Ferriin or Lead Dioxide in Aqueous and Methanolic Solutions." Zeitschrift für Naturforschung. B, A journal of chemical sciences 31.4 (1976) 427-436