The electrochemistry of some ferrocene derivatives: redox potential and substituent effects

Fifteen ferrocene derivatives I-IX (four of which have been prepared for the first time: II, IIIf, V and VIII) have been prepared by Friedel-Crafts acetylation, Claisen condensation, Michael reaction, and ring closure by hydrazine hydrate. The anodic behaviour of these compounds has been studied by cyclic voltammetry at a platinum electrode in an aprotic solvent. All these substituted ferrocenes exhibit a reversible one-electron oxidation reduction centred at each iron centre, and the effect of substituents on the half-wave oxidation potential is discussed in terms of their electronic properties. Linear correlations have been observed between these potentials and the Hammett sigma(x) constant for the substituents. Cyclic voltammetry has been carried out for ferrocene derivatives IIIa, V and IX Copyright (C) 2003 John Wiley Sons, Ltd.