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(Benzene)chromium tricarbonyl is an
(Benzene)tricarbonylchromium is a useful
organometallic compound
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and s ...
with the formula . This yellow crystalline solid compound is soluble in common nonpolar
In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end.
Polar molecules must contain one or more polar ...
organic solvents. The molecule adopts a geometry known as “ piano stool” because of the planar arrangement of the aryl
In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as ...
group and the presence of three CO ligand
In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electr ...
s as "legs" on the chromium-bond axis.
Preparation
(Benzene)tricarbonylchromium was first reported in 1957 by Fischer and Öfele, who prepared the compound by thecarbonylation
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbon ...
of bis(benzene)chromium
Bis(benzene)chromium is the organometallic compound with the formula Cr( η6-C6H6)2. It is sometimes called dibenzenechromium. The compound played an important role in the development of sandwich compounds in organometallic chemistry and is th ...
. They obtained mainly chromium carbonyl (Cr(CO)) and traces of Cr(CH)(CO). The synthesis was optimized through the reaction of Cr(CO) and Cr(CH). For commercial purposes, a reaction of Cr(CO) and benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
is used:
:Cr(CO) + CH → Cr(CH)(CO) + 3 CO
Applications
Complexes of the type (Arene)Cr(CO)3 have been well investigated as reagents in organic synthesis.. The aromatic ring of (benzene)tricarbonylchromium is substantially moreelectrophilic
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carri ...
than benzene itself, allowing it to undergo nucleophilic addition
In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic additions di ...
reactions.Herndon, James W; Laurent, Stéphane E. (2008). “(η-Benzene)tricarbonylchromium,” in Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester, 2008. . Article Online Posting Date: March 15, 2009
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It is also more acidic, undergoing lithiation upon treatment with ''n''-butyllithium. The resulting organolithium compound
In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...
can then be used as a nucleophile in various reactions, for example, with trimethylsilyl chloride
Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound ( silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. ...
:
:
(Benzene)tricarbonylchromium is a useful catalyst
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
for the hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or S ...
of 1,3-diene
In organic chemistry a diene ( ) (diolefin ( ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nomenclature. ...
s. The product alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
results from 1,4-addition of hydrogen
Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
. The complex does not hydrogenate isolated double bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...
s.
References