Eriedel-Crafts’ reaction

Eriedel-Crafts reactions [FRIEDEL-CRAFTSREACTIONS] (Volll)... 

Cross-linked macromolecular gels have been prepared by Eriedel-Crafts cross-linking of polystyrene with a dihaloaromatic compound, or Eriedel-Crafts cross-linking of styrene—chloroalkyl styrene copolymers. These polymers in their sulfonated form have found use as thermal stabilizers, especially for use in drilling fluids (193). Cross-linking polymers with good heat resistance were also prepared by Eriedel-Crafts reaction of diacid haUdes with haloaryl ethers (194). 

Eriedel-Crafts reaction of naphthalene or tetrahydronaphthalene derivatives with those of styrene or alkylbenzenes has been used in the preparation of high viscous fluids for traction drive (195). Similarly, Eriedel-Crafts reaction of tetraline and a-methylstyrene followed by catalytic hydrogenation provided l-(l-decalyl)-2-cyclohexyl propane, which is used as a highly heat resistant fluid (196). 

Polymer-type antioxidants have been prepared by Eriedel-Crafts reaction of -cresol andp- and/or y -chloromethylstyrene in the presence of boron trifluoride-etherate (198). The oligomeric product resulting from the alkylation of phenyl-a-naphthylamine using C12—15 propylene oligomer in the presence of AlCl or activated white clays is used as an antioxidant additive for lubricating oils (199). 

Other Synthesis Routes. Several alternative routes to the nucleopbilic substitution synthesis of polysulfones are possible. Polyethersulfone can be synthesized by the electrophilic Eriedel-Crafts reaction of bis(4-chlorosulfonylphen5l)ether [121 -63-1] with diphenyl ether [101-84-8] (11—13). 

This article covers important industrial technologies and the direction of future technological development. The description of alkylation chemistry and conventional alkylation technologies covered in the eadier editions of this Eniyclopedia and other references is minimized (1,2) (see also Eriedel-Crafts reactions). 

Aluminum Chloride-Based All lation. The eadier alkylation processes were variations of the Eriedel-Craft reaction on an aluminum chloride catalyst complex in a Hquid-phase reactor (27), including those developed by Dow Chemical, BASE, Monsanto, and Union Carbide in cooperation with Badger. The Union Carbide-Badger process was the one most widely used during the 1960s and 1970s, with 20 plants built worldwide. 

In the presence of Eriedel-Crafts catalysts, gaseous ethyl chloride reacts with ben2ene at about 25°C to give ethylben2ene, three diethylben2enes, and other more complex compounds (12) (see Xylenes and ethylbenzene). Aromatic compounds can generally be ethylated by ethyl chloride in the presence of anhydrous aluminum chloride (see Eriedel-Crafts REACTIONS). Ethyl chloride combines directly with sulfur trioxide to give ethyl chlorosulfonate,... 

Under the influence of a Lewis acid, Cjq can be arylated via a Eriedel-Crafts reaction (see Section 8.6). A similar reaction occurs with CggEjg where ipso substitution of fluorine atoms takes place [68]. The fluorofullerene is treated with FeClj in benzene for two weeks (Scheme 9.8). Electrophilic substitution leads to arylated C5QFjg Ph with n = 1-3. Probably due to steric reasons the 5-substitution is not observed in this arylation. 

The present catalyst was examined in a more reactive acetylation, the acetylation of anisole with acetic anhydride. A quantitative yield of methoxyacetophenone was obtained under the reaction conditions, showing how reactive anisole is in comparison with toluene-demonstrating the effect an oxygen has on reactivity. Several papers concerning the Eriedel-Crafts reaction of anisole have been published [212-216], but studies of the reaction of toluene or even benzene are desired. The difference in reactivity between anisole and toluene is close to 100 °C in terms of the reaction temperature. 

Would you expect the Eriedel-Crafts reaction of benzene with (R)-2-chloro-butane to yield optically active or racemic product Explain. 

Dihydro-177-2,Tbenzazaborole derivative 170 can be prepared by an intramolecular Eriedel-Crafts reaction of 169 <2000CC1587>, as illustrated in Equation (19). 

Zhao ZK, Yuan B, li ZS et al (2004) The environmentally benign ionic liquids and then-application in Eriedel-Crafts reactions. China Basic Sd 6(1) 19-25... 

Cyclization. Cyanoacetic esters undergo O, A-diprotonation in TfOH. If the ester bears a benzyl orphenylethyl group at the a-position, the derived dication would undergo an intramolecular Eriedel-Crafts reaction. ... 

The resins are made by batch processes employing Eriedel-Crafts reactions or nucleophilic aromatic substitution. Udel resin and Radel R resin are produced by the nucleophilic displacement of chloride on 4,4 -dichlorodiphenyl sulfone by the potassium salts of bisphenol A and 4,4 -biphenol, respectively (97) ... 

Crafts (U.S.) discover the Eriedel-Crafts reaction, in which an aluminum chloride catalyst transforms organic chlorides into hydrocarbons and acid halides into ketones. [1877]... 

A concise synthesis of the indole alkaloid ( )-actinophyllic acid was reported, in which a key step involves a cationic reaction cascade. The indole (163) is treated with TMSOTf to generate the electrophilic carbocation (164), and this reacts with a dihydroazepine to provide the A-acyliminium ion intermediate (166). A Eriedel-Crafts reaction gives the indole product (165) and the framework for actinophyllic acid (Scheme 34). 

In the case when R=C02Me or C02Et, the reaction pathway was different here the Eriedel-Crafts reaction is faster than the formation of dehydrated cation, and it... 

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