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Friedel–Crafts alkylations can be reversible. Although this is usually undesirable it can be exploited; for instance by facilitating transalkylation reactions. [10] 1,3-Diisopropylbenzene is produced via transalkylation, a special form of Friedel–Crafts alkylation. It also allows alkyl chains to be added reversibly as protecting groups.
Friedel-Crafts alkylation: alkylbenzenes can be synthesized from olefins or alkyl halides with aromatic compounds in the presence of a catalyst such as AlCl 3, HF, or H 2 SO 4. [ 4 ] Gattermann-Koch reaction : named after German chemists Ludwig Gattermann and Julius Arnold Koch , the Gattermann-Koch reaction is a catalyzed formylation of ...
This reaction is typically catalyzed by the corresponding iron or aluminum trihalide. The Friedel–Crafts reaction can be performed either as an acylation or as an alkylation. Often, aluminium trichloride is used, but almost any strong Lewis acid can be applied. For the acylation reaction a stoichiometric amount of aluminum trichloride is ...
The reaction resembles Friedel-Crafts alkylation but with opposite reactivity and selectivity. [3] The Minisci reaction often produces a mixture of regioisomers that can complicate product purification, but modern reaction conditions are incredibly mild, allowing a wide range of alkyl groups to be introduced. [4]
Chlorosulfonated alkanes are susceptible to crosslinking via reactions with various nucleophiles. [10] Sulfonyl chlorides readily undergo Friedel–Crafts reactions with arenes giving sulfones, for example: [citation needed] [dubious – discuss] RSO 2 Cl + C 6 H 6 → RSO 2 C 6 H 5 + HCl. A readily available arylsulfonyl chloride source is ...
Clemmensen reduction conditions are particularly effective at reducing aryl [4]-alkyl ketones, [5] [6] such as those formed in a Friedel-Crafts acylation. The two-step sequence of Friedel-Crafts acylation followed by Clemmensen reduction constitutes a classical strategy for the primary alkylation of arenes.
Two common modes of Lewis acid catalysis in reactions with polar mechanisms. In reactions with polar mechanisms, Lewis acid catalysis often involves binding of the catalyst to Lewis basic heteroatoms and withdrawing electron density, which in turn facilitates heterolytic bond cleavage (in the case of Friedel-Crafts reaction) or directly activates the substrate toward nucleophilic attack (in ...
In the case of the Friedel–Crafts alkylation, the reaction can be broken into three steps as follows: [1] The alkyl halide reacts with the strong Lewis acid to form an activated electrophile composed of the tetrachloroaluminate ion and the alkyl group.