Alkyl phenyl ethers

RCH=CHjj -H H3SO4 — RCHlCHjlOSOaOH Polyalkylated aromatic hydrocarbons and alkyl phenyl ethers are sulphonated ... 

Fragmentation Losses of 1(H), 28 (CO), and 29 (CHO) Daltons are commonly observed for diaryl ethers. In diphenyl ether, m/z 77 is intense, while in phenyl toluoyl ethers m/z 91 is intense, An intense peak in the mass spectra of alkyl phenyl ethers occurs at m/z 94. 

Alkyl phenyl ethers (except anisole) Dimethyl pyrroles... 

R2NC1, 91, 92 phenyl acetate, Fries rearrangement of, 475 phenyacetyl halides, acylation by, 173 2-phenylbenzoic acid, cycliacylation, 185 phenyl ethers, alkylation of, 149 —, bromination of, 130 —, hydrogen exchange with, 260 —, rearrangement of, 476 phenyl ethyl mercury, mercuridemercuration of, 359, 360... 

The oxidative dimerization of the anion of methyl phenyl sulfone (from a Grignard reagent) in ethereal solution in the presence of cupric chloride in 5% yield has been reported47. Despite the reported48 poor stability of the a-sulfonyl C-centered radicals, Julia and coworkers49 provoked the dimerization (in 13 to 56% yields) of the lithiated carbanion of alkyl phenyl sulfones using cupric salts as oxidants. The best results are obtained with cupric triflates in THF-isobutyronitrile medium (56% yield for R = H). For allyl phenyl sulfones the coupling in the 3-3 mode is predominant. 

Favretto and Tunis [198] extracted polyoxyethylene alkyl phenyl ethers as picrates into an organic solvent, complexed the polymer with sodium ion, and measured the absorption complex. This is one of the few specific methods available. 

It should be mentioned in connection with the use of 119 and its etherates that conversions of alkyl phenyl ketones to the corresponding carbinols were approximately 90%, and addition and enolization were not significant. Rates of reductions were found to be lower in the ether solvents, particularly THF, than in pentane (157). The decrease has been attributed to competition between ether and ketone for the aluminum moiety (eq. [32]). 

Sozzi, G. Audier, H.E. Mourgues, P. Milliet, A. Alkyl Phenyl Ether Radical Cations in the Gas Phase a Reaction Model. Org. Mass Spectrom. 1987, 22, 746-747. 

Morton, T.H. Ion-Molecule Complexes in Unimolecular Fragmentations of Gaseous Cations. Alkyl Phenyl Ether Molecular... 

Hamish, D. Holmes, J.L. Ion-Radical Complexes in the Gas Phase Structure and Mechanism in the Fragmentation of Ionized Alkyl Phenyl Ethers. J. Am. Chem. Soc. 1991,113,9729-9734. 

The degradation products of GOS were 1,3-dimethyl pyrogallol (HI), 2-(2 ,6 dimethoxy phenoxy)-2-propenal (Vni), 2-(2, 6 -dimethoxy phenoxy)-3-hydroxypropanal (XII), and GOS-Dimer. These products show that the reaction includes oxidative polymerization and the cleavage of -0-4 ether linkage following the alkyl-phenyl cleavage. This depolymerization pathway of GOS is also similar to that of SOS (Table I). 

Hie GOG-Dimer formed from the lignin dimer compound (GOG) by laccase III was also degraded by laccase HI, resulting in the formation of compounds (I), (VI), and biphenyl dimer of 2-methoxy-l,4-benzoquinone (DC). This indicates that GOG-Dimer also suffers the cleavage of -0-4 ether linkage via the alkyl-phenyl cleavage. 

Alkyl phenyl tellurides (general procedure) Li metal (1.4 g, 0.2 mol) in small pieces is added under N2 to a solution of diphenyl ditelluride (4.1 g, 10 mmol) in dry THF (100 mL). The mixture is stirred at room temperature for 6 h, unreacted lithium is removed using a spatula and the aUcyl halide (20 mmol) neat or in THF is added dropwise to the stirred yellowish-brown solution. The solution is stirred at room temperature for 30 min, and under reflux for an additional 30 min. The solvent is evaporated, and HjO (10 mL) and ether (25 mL) are added to the residue, mixing thoroughly. The ethereal phase is separated and evaporated. The residue is fractionally distilled under vacuum (yields 62-79%). 

Oxidation of alkyl phenyl telluride with excess meto-chloroperbenzoic acid (MCPBA) (3-5 equiv) in methanol affords the replacement of the phenyltellurium moiety by a methoxy group, giving the corresponding methyl ethers - (method A). This reaction. 

Detellurative methoxylation of alkyl phenyl tellurides (typical procedure)2-Methoxy 3-phenyltelluro-l,2,3,4-tetrahydronaphthalene (1.85 g, 5 mmol) is treated with MCPBA (3.3 g, 15 mmol) in MeOH (30 mL) at 25°C with stirring. After 1 h the mixture is treated with aqueous Na2S203 followed by aqueous NaHCOj and extracted with ether (3x30 mL). The extract is dried (MgS04) and evaporated, to leave a residue which is purified by Si02 TLC (eluting with hexane/EtOAc, 4 1) to afford pure tranx-2,3-dimethoxy-l,2,3,4-tetrahy-dronaphthalene (0.37 g, 1.94 mmol) and the c/x-isomer (0.15 g, 1.76 mmol (54%)). 

General procedure for telluroxide elimination by oxidation of alkyl phenyl tellurides in the presence of base. To a two-necked, round-bottomed flask (25 mL) containing alkyl phenyl telluride (1 mmol), triethylamine (1-2 mmol) and diethyl ether (5 mL) was added solid MCPBA (purity 80%) (2 mmol as pure MCPBA) portionwise at 25°C. The mixture was stirred with a magnetic stirrer for 2 h at the same temperature before being poured into... 

For primary alkyl phenyl ethers 47, their hthiation under catalytic conditions (DTBB, 5%) in THF at room temperature gave the expected alkyUithiums, which by reaction with carbonyl compounds afforded, after hydrolysis, the expected alcohols 48 (Scheme 15) . In this case, only the O—Caiiyi bond cleavage was observed . On the other hand, the reaction shown in Scheme 15 failed for secondary (R = i-Pr) or tertiary (R = f-Bu) starting materials. 

Silica particles synthesized in nonionic w/o microemulsions (e.g., poly-oxythylene alkyl phenyl ether/alkane/water) typically have a narrow size distribution with the average value between 25 and 75 nm [54,55]. Both water and surfactant are necessary components for the formation of stable silica suspensions in microemulsions. The amounts of each phase present in the micro emulsion system has an influence on the resulting size of the silica nanoparticle. The role of residual water (that is the water that is present in the interface between the silica particle and the surfactant) is considered important in providing stability to the silica nanoparticle in the oil... 

A test tube (25 x 150 mm) is charged with 0.10 g (measured to the nearest 0.1 mg) of the alkyl phenyl glycidyl ether, 10.00 g of 1-octanol, and 10.00 g of distilled water. The mixture is thermally equilibrated at 25.0°C and then vigorously mixed. The phases are allowed to separate, and the lower aqueous phase is carefully removed. The aqueous phase (5.0 g, measured to the nearest 0.1 mg) is serially diluted to 10.00 ml with ethanol, and the alkyl phenyl glycidyl ether concentration is measured spectrophotometrically at 275 nm. 

Tellur oxide elimination. sec-Alkyl phenyl tellurides on oxidation with CIQH4CO3H in ether afford alkenes as the major product. In some cases a stable Te(IV) compound is formed, which undergoes elimination on pyrolysis.5... 

Frothers are chemicals whose molecules contain both a polar and a nonpolar group. The purpose of a froth is to carry mineral-laden bubbles lor a period of lime until the froth can be removed from the flotation machine for recovery of ils mineral content. Typical frothing chemicals are alcohols, cresylic acids, eucalyptus oils, camphor oils, and pine oils, all of which are slightly soluble in water. Soluble frolhers in common use include alkyl ethers and phenyl ethers of propylene and polypropylene glycols. 

Commercial polymers have been produced from methyl, ethyl, isopropyl, n-butyl, isotubtyl, t-butyl, stcaryl, benzyl and trimethylsilyl vinyl ethers. The polylmethyl vinyl ether) called PVM or Resyn is produced by the polymerization of the monomer by boron trifluoride in propane at —40°C in the presence of traces of an alkyl phenyl sulfide. The polymer may have isotactic, syndiotactic or stereoblock configurations depending on the solvent and catalyst used. 

The corrinoid-mediated reduction of polyhaloethenes has been the subject of a recent study, which reports reaction via homolytic C-halogen bond fission. The elimination of a further halogen radical affords haloalkynes, which lead to acetylene itself.56 The electron transfer-induced reductive cleavage of alkyl phenyl ethers with lithium naphthalenide has been re-examined in a study which showed that it is possible to reverse regioselectivity of the cleavage (i.e. ArOR to ArH or ArOH) by introduction of a positive charge adjacent to the alkyl ether bond.57 A radical intermediate has been detected by ESR spectroscopy in the reduction of imines to amines with formic acid58 which infers reacts takes place via Lukasiewicz s mechanism.59... 

The role of polychlorinated gem-dichlorocyclohexadienones as reaction intermediates which can then produce desired me/a-chlorinated products or imdesired coupled products has been described.17 Chlorination of phenol and sometimes the ether complicates the hydrolysis of some primary alkyl phenyl ethers in concentrated aqueous perchloric acid solution.18 Unexpected chlorination has also been established in the reaction of 2-amino-5-chlorobenzophenone with HC1 in aqueous methanol (1 1 v/v), 2-amino-3,5-dichlorobenzophenone being amongst the products.19... 

Nafion-H is also very efficiently catalyzes the rearrangement of anisole, methy-lanisoles, and phenetole to ring-alkylated phenols and products of transalkylation when vapors of the alkyl aryl ethers are passed over it at temperatures higher than 160°C. At these reaction temperatures, some of the starting alkyl phenyl ethers... 

Jacquesy et al.556 have succeeded in preparing mefa-bromophenols from phenols using the Br2-HF-SbF5 system. The orf/zo-protonated phenol or alkyl phenyl ether, which is in equilibrium with the neutral precursor, reacts with the reactive Br+ in the HF-SbF5 medium, leading to only mefa-brominated phenols (Scheme 5.59). The ring protonated phenols are unreactive toward electrophilic bromine in the superacid... 

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