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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
De Luca, Carlo,Inesi, Achille,Rampazzo, Liliana
, p. 209 - 212 (2007/10/02)
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-0.1 M Et4NClO4 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).
