화학공학소재연구정보센터
Electrochimica Acta, Vol.48, No.24, 3593-3598, 2003
Electrochemical study of 7 alpha,12,20-O-trimethyl-conacytone in acetonitrile
An electrochemical study of the electroreduction in anhydrous acetonitrile of 7alpha,12,20-O-trimethyl-conacytone, an abietane quinoid diterpene derivative from the natural product 7alpha-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 7alpha-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. (C) 2003 Elsevier Ltd. All rights reserved.