(Benzylideneacetone)iron tricarbonyl
Encyclopedia
The organometallic compound (benzylideneacetone)iron tricarbonyl is a widely employed reagent for transferring the Fe(CO)3 unit to other organic molecules. This red-colored compound is commonly abbreviated (bda)Fe(CO)3. It is prepared by the reaction of Fe2(CO)9
with benzylideneacetone
, typically in refluxing diethyl ether
. The identity and purity of the compound can be determined by its IR spectrum: it absorbs strongly at 2065, 2005, and 1985 cm−1
in cyclohexane
solution.
)2 is highly reactive, the trade-off being that it is thermally sensitive. Imine
derivatives of cinnamaldehyde
, e.g. C6H5CH=CHC(H)=NC6H5, form conveniently reactive Fe(CO)3 adduct
s, which have been shown to be superior in some ways to (bda)Fe(CO)3.
(bda)Fe(CO)3 reacts with Lewis bases
to give adducts without displacement of the bda.
Diiron nonacarbonyl
Diiron nonacarbonyl is an inorganic compound with the formula Fe29. This metal carbonyl is an important reagent in organometallic chemistry and of occasional use in organic synthesis. It is a more reactive source of Fe than Fe5 and less dangerous to handle because it is nonvolatile...
with benzylideneacetone
Benzylideneacetone
Benzylideneacetone is the organic compound described by the formula C6H5CH=CHCCH3. Although both cis- and trans-isomers are possible for the α,β-unsaturated ketone, only the trans isomer is observed...
, typically in refluxing diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...
. The identity and purity of the compound can be determined by its IR spectrum: it absorbs strongly at 2065, 2005, and 1985 cm−1
Wavenumber
In the physical sciences, the wavenumber is a property of a wave, its spatial frequency, that is proportional to the reciprocal of the wavelength. It is also the magnitude of the wave vector...
in cyclohexane
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...
solution.
Related Fe(CO)3 transfer agents
A popular source of Fe(CO)3 is the simplest, Fe2(CO)9. Alternatively, Fe(CO)3(cycloocteneCyclooctene
Cyclooctene is a cycloalkene with an eight-membered ring. It is notable because it is the smallest cycloalkene that can exist as either the cis- or trans-isomer with the cis-isomer more common...
)2 is highly reactive, the trade-off being that it is thermally sensitive. Imine
Imine
An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...
derivatives of cinnamaldehyde
Cinnamaldehyde
Cinnamaldehyde is the organic compound that gives cinnamon its flavor and odor. This pale yellow viscous liquid occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum...
, e.g. C6H5CH=CHC(H)=NC6H5, form conveniently reactive Fe(CO)3 adduct
Adduct
An adduct is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components. The resultant is considered a distinct molecular species...
s, which have been shown to be superior in some ways to (bda)Fe(CO)3.
(bda)Fe(CO)3 reacts with Lewis bases
Lewis acid
]The term Lewis acid refers to a definition of acid published by Gilbert N. Lewis in 1923, specifically: An acid substance is one which can employ a lone pair from another molecule in completing the stable group of one of its own atoms. Thus, H+ is a Lewis acid, since it can accept a lone pair,...
to give adducts without displacement of the bda.