Electrohydrodimerization of 4-chloro-3-formyl-2H(1)-benzopyrans in ethanolic solutions: A comparative study
TL;DR: In this paper, the electrochemical reduction of β-chlorovinylaldehydes, 4-chloro-3-formyl-2H(1)-benzopyran and β -chlorocinnamaldehyde, was studied in buffered ethanolic solutions.
About: This article is published in Journal of Electroanalytical Chemistry.The article was published on 1989-04-25. It has received 1 citations till now. The article focuses on the topics: Double bond.
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01 Dec 1989TL;DR: The electrochemical study of β-chlorovinylaldehydes was carried out in DMF in the presence of 0·1 M NBu4ClO4 as the supporting electrolyte as mentioned in this paper.
Abstract: The electrochemical study of β-chlorovinylaldehydes, namely, 4-chloro-3-formyl-2H (1)-benzopyran and β-chlorocinnamaldehyde was carried out in DMF in the presence of 0·1 M NBu4ClO4 as the supporting electrolyte. Both the depolarizers give three diffusionlimited polarographic waves and the corresponding cathodic peaks in cyclic voltammetry. Their microcoulometric data indicate a transfer of four-electrons (n app=4) in the electrode process. The macroscale controlled-potential electrolysis of the depolarizers afforded only blackish-brown tarry product. A mechanism is suggested for their reduction in DMF under polarographic conditions.
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TL;DR: In this article, a combination of polarographische und elektrochemisch-praparative untersuchungen haben zu folgenden Ergebnissen gefuhrt.
Abstract: Kombinierte polarographische und elektrochemisch-praparative Untersuchungen haben zu folgenden Ergebnissen gefuhrt:
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Aus der Hohe der polarographischen Stufe kann mit Zuverlassigkeit der Elektronenverbrauch pro Molekel abgeschatzt werden.
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Bei in l,2-Stellung ungesattigten Ketonen ruft immer die Athylenbindung die erste Stufe im Polarogramm hervor.
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Sowohl die Carbonyl- als auch die Athylenbindung werden in zwei einelektronischen Schritten reduziert, wobei als Zwischenprodukt ein Radikal entstehen muss.
Ein moglicher Mechanismus fur den Reduktionsverlauf wurde dargestellt und diskutiert.
120 citations
92 citations
61 citations
TL;DR: In this article, Cinnamaldehyde is reduced at the dropping mercury electrode in two main two-electron steps, in the first the CC double bond is reduced and in the second the aldehydic group.
Abstract: Cinnamaldehyde is reduced at the dropping mercury electrode in two main two-electron steps. In the first the CC double bond is reduced, in the second the aldehydic group. The rate of dehydration of 3-phenylpropionaldehyde governs the height of the more negative step. In acid media the first two-electron process is split into two one-electron steps. The radical formed in the first one-electron step can react with cations and the adduct formed gives a separate wave iN. In electrolyses with electrodes which do not have a periodically renewed surface (mercury pool and hanging mercury drop electrodes, single-sweep techniques) the radical formed undergoes further reactions and can eventually polymerize.
35 citations