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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.
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 ...
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]
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.
Cyclopentadienyl magnesium bromide undergoes a complex reaction with iron(III) chloride, resulting in ferrocene: [31] 3 C 5 H 5 MgBr + FeCl 3 → Fe(C 5 H 5) 2 + 1/n (C 5 H 5) n + 3 MgBrCl. This conversion, although not of practical value, was important in the history of organometallic chemistry where ferrocene is emblematic of the field. [32]
Ferrocenophanes, also called ansa ferrocenes (from ansa: handle in greek), are organometallic compounds which are derived from ferrocene. They are a subset of ansa-metallocenes in which the metal is iron. In this compound class, the cyclopentadienyl ligands of the ferrocene are connected by one or more bridging groups. This hinders the rotation ...
By linking ferrocene units to small silicon-containing dendrimers, some of these first-type dendrimers can be made. [3] Dendritic macromolecules with peripheral ferrocene groups are usually synthesized by linking ferrocene to the core through olefin metathesis or hydrosilylation [1].