Cathodic reduction of ethyl α-bromonaphthalene-1- and -2-acetate: electrochemical synthesis and voltammetric behaviour of meso- and DL-diethyl 2,3-di-1- and -2-naphthylsuccinate

Abstract

Diethyl 2,3-dinaphthylsuccinates (5)–(8) can be prepared through electrochemical reduction of ethyl α-bromonaphthalene-1- and -2-acetate (3) or (4)(ABr) in DMF–0.1M-Et₄NC10₄ at a vitreous carbon electrode. These dinaphthylsuccinates (5)–(8)(A-A) are good model systems for the study of electron transfer to molecules containing two identical redox centres. Cyclic voltammetry shows that dimeric species A-A are reduced at more positive potentials than the corresponding AH compound; meso-diethyl 2,3-di-2-naphthylsuccinate (7) is reduced at a slightly more positive potential than the corresponding DL-succinate (8). The 1-naphthyl derivatives are more easily reduced than the corresponding 2-naphthyl compounds, the difference being larger between bromoesters (3) and (4).