Tetrahedron Letters,Vol.28,No.48,pp 6081-6084,1987 0040-4039/87 $3.00 + .Oo Printed in Great Britain Pergamon Journals Ltd. ELECTRO-ORGANICREACTIONS. PART 32. ELECTROGENERATEDBASES FROM QUINONEMETHIDES Marilia O.F. Goulart, Sim K. Ling-Chung and James H.P. Utley* Department of Chemistry, Queen Mary College, London El IINS, U.K. Abstract: The radical-anion of fuchsone (11, and the dianions of related quinonemethides, are generated at low cathodic potentials and act as bases in high yielding Wittig reactions; the phenolic product may be oxidatively reconverted into quinonemethide. Organic dianions and radical-anions, generated cathodically from zyxwvutsrqponmlkjihgfedcbaZY probases, have been successfully used as bases.' For in situ generation of anionic bases the relevant reduction potentials of the probase must be lower than those of the other reactants and products. Steric hindrance at the basic centre is also an advantage as it reduces nucleophilicity. Where the probase is expensive or difficult to prepare, convenient regeneration from the protonated form is desirable; this has been achieved in some cases by chemical or electrochemical oxidations 273 . We demonstrate herein that the radical-anion of the quinonemethide (1) and the dianions of (2) and (31, have useful basic properties; the hydrogenated products, the corresponding phenols, are conveniently re-oxidised to quinonemethide. The radical-anions are formed at modest potentials yet function as useful oxygen-anion bases in aprotic solvent. (4) zyxwvutsrqponmlkjihgfed OH &Bu t.Bu (6) 6081