Abstract
AbstractThe electrochemical oxidation of catechols (1) have been studied in the presence of diaza‐18‐crown‐6 (DA18C6) (3a), diaza‐15‐crown‐5 (DA15C5) (3b), and aza‐15‐crown‐5 (A15C5) (3c) as nucleophiles in aqueous solution, by means of cyclic voltammetry and controlled‐potential coulometry. The results indicate the participation of electrochemically generated o‐benzoquinones (2) in Michael‐type reaction with aza‐crown ethers (3) to form the corresponding new o‐benzoquinone‐aza‐crown ether adducts (5). Based on ECE mechanism, the observed homogeneous rate constants (kobs) of the reaction of o‐bezoquinones (2) with aza‐crown ethers (3) were estimated by comparing the experimental cyclic voltammograms with the digital simulated results. The calculated observed homogeneous rate constants (kobs) was found to vary in the order DA18C6>DA15C5>A15C5.
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