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The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. [1] Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution. [2] [3] [4] [5]
The association is strongest as a covalent bond and weakest when the pair exists as free ions. [6] In cationic polymerization, the ions tend to be in equilibrium between an ion pair (either tight or solvent-separated) and free ions. [2] The more polar the solvent used in the reaction, the better the solvation and separation of the ions.
Oxalyl chloride reacts with aromatic compounds in the presence of aluminium chloride to give the corresponding acyl chloride in a process known as a Friedel-Crafts acylation. [ 15 ] [ 16 ] The resulting acyl chloride can be hydrolysed to form the corresponding carboxylic acid .
Phenols react to form esters instead of hydroxyarylketones when reacted with acyl halides under Friedel-Crafts acylation conditions. Therefore, this reaction is of industrial importance for the synthesis of hydroxyarylketones, which are important intermediates for several pharmaceuticals.
In electrophilic substitution in aromatic compounds, an atom appended to the aromatic ring, usually hydrogen, is replaced by an electrophile.The most important reactions of this type that take place are aromatic nitration, aromatic halogenation, aromatic sulfonation and acylation and alkylating Friedel-Crafts reactions.
Cumene is formed in the gas-phase Friedel–Crafts alkylation of benzene by propene. Benzene and propene are compressed together to a pressure of 30 standard atmospheres at 250 °C in presence of a catalytic Lewis acid. Phosphoric acid is often favored over aluminium halides.
The methylene group in diphenylmethane is mildly acidic with a pK a of 32.2, and so can be deprotonated with sodium amide. [3](C 6 H 5) 2 CH 2 + NaNH 2 − → (C 6 H 5) 2 CHNa + NH 3. The resulting carbanion can be alkylated.
Friedel–Crafts reaction, a type of organic reaction developed by Charles Friedel and James Crafts in 1877. Friedel's law, named after Georges Friedel, the crystallographer, is a property of Fourier transforms of real functions. Friedel's salt, discovered by Georges Friedel, is an anion exchanger mineral belonging to the family of the layered ...