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Simple methods have been developed for the preparation of a series of n-alkylferrocenes H(CH2)Fc (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 watersoluble cations H(CH2)nFc+ in the absence of micelles were studied by cyclic voltammetry. In all cases, the formal redox potentials of ferrocenes (£ ‘) increase linearly as n increases up to 8. Whether micelles are present or not, the corresponding correlation equation has the following form: £”‘= a + pn, where beta= 29 mV in all cases. The synthesis of (±)-l-ethyI-2methylferrocene from racemic a-dimethylaminoethylferrocene is reported.
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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis