Ethers with aromatic rings

Besides 11-15-11-17, several other formylation methods are known. In one of these, dichloromethyl methyl ether formylates aromatic rings with Friedel-Crafts catalysts.The Compound ArCHClOMe is probably an intermediate. Orthoformates have also been used. In another method, aromatic rings are formylated with... 

Besides 1-15 to 1-17, several other formylation methods are known.302 In one of these, dichloromethyl methyl ether formylates aromatic rings with Friedel-Crafts catalysts.303 ArCHClOMe is probably an intermediate. Orthoformates have also been used.304 In another method, aromatic rings are formylated with formyl fluoride HCOF and BF3.305 Unlike formyl chloride, formyl fluoride is stable enough for this purpose. This reaction was successful for benzene, alkylbenzenes, PhCl, PhBr, and naphthalene. Phenols can be regioselectively formylated in the ortho position in high yields by treatment with two equivalents of paraformaldehyde in aprotic solvents in the presence of SnCL and a tertiary amine.306 Phenols... 

Extensive work by Yamaki and Tobishima was devoted to the effect of additives on Li cycling efficiency in ethers and alkyl carbonates [265], This included the use of cation complexing compounds (e.g., 12 crown 4, TMEDA), reactive organic compounds (e.g., quinoneimine derivatives), and adsorption compounds (e.g., large tetraalkyl ammonium chloride substituted with aromatic rings) [265],... 

Evidence from spectral studies for interactions other than the above hydrogen bonds is not very plentiful. Polystyrene/poly(2,6 dimethyl-l,4-phenylene oxide) blends have been studied by infra-red and ultraviolet spectroscopy . Interactions involving the aromatic rings of the two polymers were proposed. Studies of low molecular weight ethers with aromatic compounds have shown evidence for specific interactions and this has recently been extended to blends of polystyrene with poly(methyl vinyl ether)... 

Ethers are characterized by the —O— functional group, where the oxygen atom links either alkyl or aromatic groups. Cyclic ethers, with various ring sizes, are called epoxides. O... 

Crown ethers possess oxygen atoms (137), sulfur atoms,233 (138) or different donor atoms as in (139) and (140). Polyaza-macrocycles are treated by other authors. Two or three carbon atoms are generally interposed between each pair of donor atoms many ligands with aromatic rings fused to the macrocycle have been reported. 

The Hoesch Reaction is employed for the introduction of the - COR group into the aromatic ring of phenol or a phenolic ether, and usually proceeds particularly readily with polyhydric phenols. If an ethereal solution of resorcinol (I)... 

The aromatic core or framework of many aromatic compounds is relatively resistant to alkylperoxy radicals and inert under the usual autoxidation conditions (2). Consequentiy, even somewhat exotic aromatic acids are resistant to further oxidation this makes it possible to consider alkylaromatic LPO as a selective means of producing fine chemicals (206). Such products may include multifimctional aromatic acids, acids with fused rings, acids with rings linked by carbon—carbon bonds, or through ether, carbonyl, or other linkages (279—287). The products may even be phenoUc if the phenoUc hydroxyl is first esterified (288,289). 

Weak Base Anion Exchangers. Both styreoic and acryHc copolymers can be converted to weak base anion-exchange resias, but differeat syathetic routes are aecessary. Styreae—DVB copolymers are chloromethylated and aminated ia a two-step process. Chloromethyl groups are attached to the aromatic rings (5) by reactioa of chloromethyl methyl ether [107-30-2] CH2OCH2CI, with the copolymer ia the preseace of a Friedel-Crafts catalyst such as aluminum chloride [7446-70-0], AlCl, iroa(III) chloride [7705-08-0], FeCl, or ziac chloride [7646-85-7], ZaCl. ... 

One class of aromatic polyethers consists of polymers with only aromatic rings and ether linkages ia the backbone poly(phenylene oxide)s are examples and are the principal emphasis of this article. A second type contains a wide variety of other functional groups ia the backbone, ia addition to the aromatic units and ether linkages. Many of these polymers are covered ia other articles, based on the other fiinctionahty (see Polymers containing sulfur, POLYSULFONES). 

The chemical production of aminophenols via the reduction of nitrobenzene occurs in two stages. Nitrobenzene [98-95-3] is first selectively reduced with hydrogen in the presence of Raney copper to phenylhydroxylamine in an organic solvent such as 2-propanol (37). With the addition of dilute sulfuric acid, nucleophilic attack by water on the aromatic ring of /V-phenylhydroxylamine [100-65-2] takes place to form 2- and 4-aminophenol. The by-product, 4,4 -diaminodiphenyl ether [13174-32-8] presumably arises in a similar manner from attack on the ring by a molecule of 4-aminophenol (38,39). Aniline [62-53-3] is produced via further reduction (40,41). 

Like other aromatic compounds, aromatic ethers can undergo substitution in the aromatic ring with electrophilic reagents, eg, nitration, halogenation, and sulfonation. They also undergo Eriedel-Crafts (qv) alkylation and acylation. 

Na, /-BuOH, 70-80°, 2 h, 78%. In this example sodium in /-butyl alcohol cleaves two aiyl benzyl ethers and reduces a double bond that is conjugated with an aromatic ring nonconjugated double bonds are stable. 

The styrene double bond in 9(ll)-dehydroestradiol 3-methyI ether (1) or its 8-dehydro counterpart is reduced by potassium or lithium in ammonia without affecting the aromatic ring estradiol 3-methyl ether (2) is formed from both compounds. Reduction of the corresponding 17-ketones occurs with partial or complete reduction of the carbonyl group. Lithium... 

After completion of the reaction, the mixture is diluted with water, extracted with ether and the residue from the ether phase purified by chromatography and/or recrystallization. If the substrate contains aromatic protons, the reduction procedure is repeated in protic medium to back exchange deuteriums incorporated into the aromatic ring. 

As shovm above, the attachment of the aromatic ring to the carbon chain bearing the basic nitrogen may be accomplished through an ester or an amide configured in either direction. A simple ether linkage fulfills this function in yet another compound that exhibits local anesthetic activity. Thus, alkylation of the mono potassium salt of hydroquinone with butyl bromide affords the ether (77) alkylation of this with w-C3-chloropropyl)morpholine affords pramoxine (78)... 

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