Preparation and structural characterisation of a novel ferrocene–amino acid conjugate

A new type of ferrocene–amino acid conjugate, 2-[(methoxycarbonyl)methyl]-2-aza[3]ferrocenophane (1), was obtained in a rather low yield via condensation reaction of 1,1′-bis(hydroxymethyl)ferrocene and glycine methyl ester in the presence of [RuCl2(PPh3)3] as a catalyst. The compound was characterised by combustion analysis and by spectroscopic method, and its solid-state structure was established by single-crystal X-ray diffraction analysis. Compound 1 is reluctant towards alkylation with MeI but readily forms a stable picrate salt. Cyclic voltammetry experiments on 1 (in CH3CN at Pt electrode) revealed the compound to undergo a one-electron reversible oxidation attributable to ferrocene/ferrocenium couple (Eo′ = −5 mV vs. ferrocene itself), which shifts towards more positive potentials upon protonation with HCl.

A ferrocene-glycine conjugate, 2-[(methoxycarbonyl)methyl]-2-aza[3]ferrocenophane (see the crystal structure), was obtained by Ru-catalysed condensation 1,1′-bis(hydroxymethyl)ferrocene with glycine methyl ester and was structurally characterised by a combination of spectroscopic methods, X-ray crystallography and cyclic voltammetry.Figure optionsDownload as PowerPoint slide