Electrochemical chlorination of azulene derivatives: Insight into the mechanism of anodic oxidative chlorination |
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Authors: | Eleonora M. Ungureanu Liviu Birzan George Buica Enache Cristian |
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Affiliation: | a University Polytechnica of Bucharest, Faculty of Industrial Chemistry, 132 Calea Grivitei, 78122 Bucharest, Romania b Institute of Organic Chemistry “C.D. Nenitzescu” of Romanian Academy, 202B-Splaiul Independentei, P.O. Box 15-254, 60023 Bucharest, Romania |
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Abstract: | The cyclic voltammetry behavior of a series of five 1-substituted azulenes has been investigated as well as the electrochemical chlorination of these compounds. In the case of azulene compounds containing electron withdrawing groups which have higher oxidation potentials than that of the chloride ion, the electrochemical chlorination led usually to 3-chloro derivatives. The electrochemical chlorination fails for azulenes with lower oxidation potentials. Additionally some polyhalogenated compounds were obtained by controlled potential electrolyses. The paper also discusses the reaction mechanism of the electrochemical halogenation of 1-substituted azulenes. |
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Keywords: | Cyclic voltammetry Azulenes Electrochemical halogenation Controlled potential electrolysis Reaction mechanism |
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