Bond cleavage in hydroxyl derivatives initiated by electron transfer: electroreduction of 9H,9’H-bifluorene-9,9’-diol

Cyclic voltammetry, digital simulation and quantum chemical methods were applied to study the electroreduction mechanism of vicinal hydroxyl derivatives using 9H,9’H-bifluorene- 9,9’-diol as an example. Unlike the case of fluoren-9-ol, dissociation of the C⁹–C^9’ bond rather than the C⁹–OH one occurs in radical anion of the substrate, similarly to that in radical cations formed upon oxidation of vicinal hydroxyl derivatives.