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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.
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.
1,1 ′-Bis(diphenylphosphino)ferrocene, commonly abbreviated dppf, is an organophosphorus compound commonly used as a ligand in homogeneous catalysis. It contains a ferrocene moiety in its backbone, and is related to other bridged diphosphines such as 1,2-bis(diphenylphosphino)ethane (dppe).
Acetylferrocene is prepared by Friedel-Crafts acylation of ferrocene, usually with acetic anhydride (Ac 2 O): . Fe(C 5 H 5) 2 + Ac 2 O → (C 5 H 5)Fe(C 5 H 4 Ac) + HOAc. The experiment is often conducted in the instructional laboratory to illustrate acylation as well as chromatographic separations.
Since the early 1960s ferrocene has been gaining acceptance as the standard reference for nonaqueous work for a number of reasons, and in 1984, IUPAC recommended ferrocene (0/1+) as a standard redox couple. [8] The preparation of the QRE electrode is simple, allowing for a fresh reference to be prepared with each set of experiments.
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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].