Electrochemical reduction of N-aryl- and N-arylsulphonylbenzoquinonemonoimines in acetonitrile—I. Electroreduction mechanism and effects of proton donors on electrochemical process

摘要: Abstract Electrochemical reduction of 1,4-benzoquinonemonoimine derivatives have been studied in acetonitrile. As a rule monoimines proceeds two steps, the first them results formation an anion-radical. Introduction sulpho-group between quinoneimine and aryl moieties leads to considerable increase electronacceptor properties compounds under investigation decrease their products nucleophilicity. In case quinonemonoiminium perchlorates electrochemical also one-electron steps. The binding nitrogen lone pair electrons change total charge system during protonation molecules anodic shift wave about 1.2 V. free radical forming electron transfer seems be reduced by more positive potentials as initial quinoneimines.