On the Savéant's Concerted/Stepwise Model. The Electroreduction of Halogenated Naphthalene Derivatives as a Case Study

The electroreduction of 1-Br-2-naphthol is shown to be a not-additive process with respect to the results obtained with two structurally related chiral [1,1′-Binaphthalene]-2,2′-diol, 6,6′-dibromo and 1,1′-Binaphthalene,6,6′-dibromo-2,2′-dimethoxy compounds. The 1-Br-2-naphtol reduction is accompanied by the carbon bromine dissociation, eventually producing a film due to a fast radical-radical cross reaction. The film formation is not observed in the BINOL-like chiral halogen-derivatives.