Electrochemical study of 7α,12,20-O-trimethyl-conacytone in acetonitrile |
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Authors: | Carlos Frontana Ignacio González |
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Affiliation: | a UAM-Iztapalapa, Departamento de Qu?́mica, Apartado Postal 55-534, Mexico City 09340, Mexico b Laboratorio de Electroqu?́mica y Electros?́ntesis, Instituto de Qu?́mica de la Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacan C.P. 04510, Mexico |
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Abstract: | An electrochemical study of the electroreduction in anhydrous acetonitrile of 7α,12,20-O-trimethyl-conacytone, an abietane quinoid diterpene derivative from the natural product 7α-O-methyl-conacytone, showed two reduction signals. At the first reduction step, fast chemical reactions involving the loss of the methoxyl group located at C-7 with simultaneous regeneration of the quinoid moiety were observed. This electrogenerated quinone is reduced again, at the same potential used with the former quinone, resulting in a two-electron peak. These results were obtained by cyclic voltammetry and double-step chronoamperometry experiments. The electrolysis under methylating conditions of 7α-O-methyl-conacytone, at potential values of the second electron transfer, generates as major products, methoxy-hydroquinone, where the methoxy group at C-7 is lost, which is in agreement with the proposed mechanism. Therefore, the second reduction signal was attributed to the reduction of semiquinone intermediates by a mechanism not elucidated. |
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Keywords: | Quinones Conacytone Deoxygenation Electroreduction Chronoamperometry Voltammetry |
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