Synthesis and electrochemical properties of mono- and (±)-1,2-dialkylferrocenes and alkylferrocenium hexafluorophosphates in aqueous and micellar media

Absract Simple methods have been developed for the preparation of a series ofn-alkylferrocenes H(CH2)nFc (n = 3, 5–8, or 12) based on Friedel-Crafts acylation of ferrocenes followed by reduction of the corresponding ketones with Zn amalgam. The properties of H(CH2)nFc and the corresponding ferrocenium ions in micellar aqueous solutions and the behavior of water-soluble cations H(CH2)nFc+ in the absence of micelles were studied by cyclic voltammetry. In all cases, the formal redox potentials of ferrocenes (Eo') increase linearly asn increases up to 8. Whether micelles are present or not, the corresponding correlation equation has the following form:Eo'= a + ßn, where ß = 29 mV in all cases. The synthesis of (±)-1-ethyl-2-methylferrocene from racemic a-dimethylaminoethylferrocene is reported.