Methyl benzyl ether, oxidation

SuIfona.tlon, Sulfonation is a common reaction with dialkyl sulfates, either by slow decomposition on heating with the release of SO or by attack at the sulfur end of the O—S bond (63). Reaction products are usually the dimethyl ether, methanol, sulfonic acid, and methyl sulfonates, corresponding to both routes. Reactive aromatics are commonly those with higher reactivity to electrophilic substitution at temperatures > 100° C. Tn phenylamine, diphenylmethylamine, anisole, and diphenyl ether exhibit ring sulfonation at 150—160°C, 140°C, 155—160°C, and 180—190°C, respectively, but diphenyl ketone and benzyl methyl ether do not react up to 190°C. Diphenyl amine methylates and then sulfonates. Catalysis of sulfonation of anthraquinone by dimethyl sulfate occurs with thaHium(III) oxide or mercury(II) oxide at 170°C. Alkyl interchange also gives sulfation. 

Carbocations can also be generated during the electrolysis, and they give rise to alcohols and alkenes. The carbocations are presumably formed by an oxidation of the radical at the electrode before it reacts or diffuses into solution. For example, an investigation of the electrolysis of phenylacetic acid in methanol has led to the identification of benzyl methyl ether (30%), toluene (1%), benzaldehyde dimethylacetal (1%), methyl phenylacetate (6%), and benzyl alcohol (5%), in addition to the coupling product bibenzyl (26%). ... 

Ruthenium tetroxide is a potent oxidant, however, and it readily attacks carbon-carbon double bonds.19 Primary alcohols are oxidized to carboxylic acids, methyl ethers give methyl esters, and benzyl ethers are oxidized to benzoate esters. 

The oxidation behavior of 3-oxa-chromanols was mainly studied by means of the 2,4-dimethyl-substituted compound 2,4,5,7,8-pentamethylM /-benzo[ 1,3]dioxin-6-ol (59) applied as mixture of isomers 27a it showed an extreme dependence on the amount of coreacting water present. In aqueous media, 59 was oxidized by one oxidation equivalent to 2,5-dihydroxy-3,4,6-trimethyl-acetophenone (61) via 2-(l-hydroxyethyl)-3,5,6-trimethylbenzo-l,4-quinone (60) that could be isolated at low temperatures (Fig. 6.41). This detour explained why the seemingly quite inert benzyl ether position was oxidized while the labile hydroquinone structure remained intact. Two oxidation equivalents gave directly the corresponding para-quinone 62. Upon oxidation, C-2 of the 3-oxa-chroman system carrying the methyl substituent was always lost in the form of acetaldehyde. 

Chloro-3-hydrox34oluene, see p-Chloro-ro-cresol 2-Chloroisopropyl ether, see Bis(2-chloroisopropyl) ether p-Chloroisopropyl ether, see Bis(2-chloroisopropyl) ether Chloromethane, see Methyl chloride (Chloromethyl)benzene, see Benzyl chloride Chloromethyl bromide, see Bromochloromethane Chloromethyl ether, see sym-Dichloromethyl ether (Chloromethyl)ethylene oxide, see Epichlorohydrin (2-Chloro-l-methylethyl) ether, see Bis(2-chloroisoprop-yl)... 

A study of the photo-sensitized ring-opening reactions of the radical cations (76) of arylcyclopropanes (75) with methanol, water, and cyanide nucleophiles suggests a three-electron 5k2 mechanism (Scheme 11).185 The isolated products are methyl propyl ethers, derived from nucleophilic attack of methanol on the radical cation (76). They were detected by UV-VIS spectroscopy and shown to react with nucleophiles by transient kinetic methods. The benzyl radical (77) reacts with the DCB radical anion to afford monoaromatic ether (78) by oxidation and protonation or the disubstituted ether (79) by addition of DCB. Regio- and stereo-selectivity of the substitution were complete regiochemistry and rate constant were profoundly effected by the electronic nature of the aryl substituents.186 Elsewhere, a combined ab initio and CIDNP study... 

Oxidation of allyl (or benzyl) methyl ethers.1 These ethers are oxidized by DDQ in refluxing toluene to carbonyl compounds. 

Treatment of the benzylated methyl 5-thio-D-glucopyranoside 7667 with ZnCl2 in dichloromethyl methyl ether (DCMME) gave the corresponding chloride, which was immediately oxidized to the chlorosulfone 77 in 40% overall yield. Treatment of 77 with I-BuOK in THF gave cyclopentene 78 in 40% overall yield (Scheme 11).62>68... 

Selenium dioxide, Se02 (mp 315 °C, sublimes), and selenious acid, H2Se03, which is obtained by the evaporation of an aqueous solution of Se02 [507, 50S], are very selective oxidants. They are capable of mild dehydrogenation to form double bonds [375] and can oxidize alkenes and acetylenes to vicinal dicarbonyl compounds [509, 510] and allylic ethers to aldehydes [511]. The most important applications are conversions of alkenes into allylic alcohols [5i2] of benzylic, methyl, or methylene groups into carbonyl groups [513, 514, 5i5] and of carbonyl compounds into a-... 

The oxidation products of mixed ethers may differ when different oxidants are used. Whereas ruthenium tetroxide oxidizes benzyl methyl... 

Biodegradable polyesters were synthesized via ring-opening copolymerizations of various oxiranes (glycidyl phenyl ether, benzyl glycidate, glycidyl methyl ether, styrene oxide) and various dicarboxylic anhydrides (succinic anhydride, phthalic... 

Scheme 4.26 Basic enzymatic polymerization of oxiranes (Glycidyl phenyl ether GPE benzyl glycidate BG glycidyl methyl ether GME styrene oxide SO) and dicarboxylic anhydrides (succinic anhydride SA maleic anhydride MA phthalic anhydride PA).

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