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Ferrocene is an organometallic compound with the formula Fe(C 5 H 5) 2.The molecule is a complex consisting of two cyclopentadienyl rings sandwiching a central iron atom. It is an orange solid with a camphor-like odor that sublimes above room temperature, and is soluble in most organic solvents.
Ferrocene is also a structurally unusual scaffold as illustrated by the popularity of ligands such as 1,1'-bis(diphenylphosphino)ferrocene, which are useful in catalysis. [17] Treatment of ferrocene with aluminium trichloride and benzene gives the cation [CpFe(C 6 H 6)] +. Oxidation of ferrocene gives the blue 17e species ferrocenium.
Ferrocenecarboxaldehyde, owing to the versatility of the formyl group, is a precursor to many ferrocene-modified compounds. With a Wittig reagent, it converts to vinylferrocene and related derivatives. [5] With primary amines, ferrocenecarboxaldehyde condenses to give imines. The azomethine derivative undergoes 1,3-cycloaddition to C 60. [6]
Iron shows the characteristic chemical properties of the transition metals, namely the ability to form variable oxidation states differing by steps of one and a very large coordination and organometallic chemistry: indeed, it was the discovery of an iron compound, ferrocene, that revolutionalized the latter field in the 1950s. [1]
Space-filling model of ferrocene, the archetypal sandwich compound. In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by haptic, covalent bonds to two arene (ring) ligands. The arenes have the formula C n H n, substituted derivatives (for example C n (CH 3) n) and heterocyclic derivatives (for ...
Polyferrocenes are polymers containing ferrocene units. Ferrocene offers many advantages over pure hydrocarbons when used as a building block of macromolecular chemistry. The variety of possible substitutions at the ferrocene parent body results in a multitude of accessible polymers with interesting electronic and photonic properties. Many ...
Nozaki’s ferrocene derivative provided products that were only 86% optically pure. Ugi, et al. improved the stereoselectivity by using [1-(dimethylamino)ethyl]-ferrocene, providing products that had an optical purity >95%. The utility of Ugi’s amine in forming ligands for asymmetric catalysis was first reported in 1974 by Kumada, et al. [6]
Ferrocenium salts are sometimes used as one-electron oxidizing agents, and the reduced product, ferrocene, is inert and readily separated from ionic products. The ferrocene–ferrocenium couple is often used as a reference in electrochemistry. The standard potential of ferrocene-ferrocenium is dependent on specific electrochemical conditions. [2]