2.5- Dimethyl-4- phenyl benzyl ether

Stability. Polymer composites doped with 2,5-dimethyl-4-(4 -nitrophen-ylazo)phenyl benzyl ether are phase stable, while composites doped with 2,5-dimethyl-4-(4 -nitrophenylazo)phenyl octyl ether show a critical concentration of 47%. Above this concentration, the composite rapidly degrades due to the crystallization of the dye. ... 

Azadienes of this sort were studied simultaneously by Mariano et al., who reacted mixtures of (1 ,3 ) and (1E, 3Z)-l-phenyl-2-aza-l,3-pentadiene 275 with several electron-rich alkenes, e.g., enamines and enol ethers (85JOC5678) (Scheme 61). They found the (l ,3 )-stereoisomer to be reactive in this process affording stereoselectively endo 276 or exo 277 piperidine cycloadducts in 5-39% yield, after reductive work-up with sodium borohydride. The stereochemistry of the resulting adducts is in agreement with an endo transition state in the case of dienophiles lacking a cis alkyl substituent at the /8-carbon (n-butyl vinyl ether, benzyl vinyl ether, and 1-morpholino cyclopentene), whereas an exo transition state was involved when dihydropyrane or c/s-propenyl benzyl ether were used. Finally, the authors reported that cyclohexene and dimethyl acetylenedi-carboxylate failed to react with these unactivated 2-azadienes. 

Dimethyl-5-phenylisoxazolium perdilorate allowed to react at 0° with benzyl-magnesium diloride in ether 2,4-dimethyl-3-benzyl-5-phenyl-4-isoxazoline (Y 81.2%) refluxed 2.5 hrs. in xylene l,2-dimethyl-3,4-diphenylpyrrole (Y 60.6%). F. e. s. I. Adadii, K. Harada, and H. Kano, Tetrah. Let. 1969, 4875 from isoxazolines s. a. G. Schmidt, H.-U. Strache, and E. Winterfeldt, B. 103, 3196 (1970). 

Benzaldehyde dimethyl acetal Cumene hydroperoxide 3,5-Dimethoxytoluene Ethoxy-p-cresol Ethylene glycol benzyl ether 4-Ethylguaiacol Methylphenoxyethanol Phenoxyisopropanol Propylene glycol phenyl ether C9H12O3... 

Amyl phenylacetate p-t-Butyl phenyl glycidyl ether Dimethyl benzyl carbinyl propionate a,a-Dimethylbenzyl isobutyrate 0-Ethyl benzyl butyrate Hexyl benzoate Isoamyl phenylacetate Methyl p-t-butylphenylacetate... 

Phenol cmtinued) Cumene Mesitylene Propylbenzene Pseudocumene Benzyl ethyl ether Phenyl propyl ether N, N-Dimethyl-o-toluidine Phorone... 

Directed lithiation of aromatic compounds is a reaction of broad scope and considerable synthetic utility. The metalation of arenesulfonyl systems was first observed by Gilman and Webb and by Truce and Amos who reported that diphenyl sulfone is easily metalated at an orf/io-position by butyllithium. Subsequently, in 1958, Truce and coworkers discovered that metalation of mesityl phenyl sulfone (110) occurred entirely at an orf/io-methyl group and not at a ring carbon, as expected. Furthermore, refluxing an ether solution of the lithiated species resulted in a novel and unusual variation of the Smiles rearrangement and formation of 2-benzyl-4,6-dimethyl-benzenesulfinic acid (111) in almost quatitative yield (equation 78). Several other o-methyl diaryl sulfones have also been shown to rearrange to o-benzylbenzenesulfinic acids when heated in ether solution with... 

Etherification of isohexides with substituted-benzyl chloride in aqueous sodium hydroxide, or by means of sodium hydride in dimethyl sulfoxide, yields mixtures of mono- and bis-ethers, which can be conventionally separated by distillation or by column chromatography.176 The preparation of some phenyl ethers was also described, using the tosylate-phenoxide exchange reaction. Monoethers (88) synthesized in this way were transformed into carbamates (89) by reaction with sodium cyanide-trifluoroacetic acid (see Scheme 18). 

Ac, acetyl AIBN, azobis(isobutanonitrile) All, allyl AR, aryl Bn, benzyl f-BOC, ferf-butoxycarbonyl Bu, Butyl Bz, benzoyl CAN, ceric ammonium nitrate Cbz, benzyloxycarbonyl m-CPBA, m-chloroperoxybenzoic acid DAST, diethylaminosulfur trifluoride DBU, l,8-diazabicyclo[5.4.0]undec-7-ene DCC, /V. /V - d i eye I oh e x y I c ar bo -diimide DCM, dichloromethyl DCMME, dichloromethyl methyl ether DDQ, 2,3-dichloro-5,6-dicyano-l,4-benzoquinone DEAD, diethyl azodicarboxylate l-(+)-DET, L-(+)-diethyl tartrate l-DIPT, L-diisopropyl tartrate d-DIPT, D-diisopropyl tartrate DMAP, 4-dimethylaminopyridine DME, 1,2-dimethoxyethane DMF, /V./V-dimethylformamide DMP, 2,2-dimethoxypropane Et, ethyl Im, imidazole KHMDS, potassium hexamethyldisilazane Me, methyl Me2SO, dimethyl sulfoxide MOM, methoxymethyl MOMC1, methoxymethyl chloride Ms, methylsulfonyl MS, molecular sieves NBS, N-bromosuccinimide NIS, /V-iodosuccinimide NMO, /V-methylmorpho-line N-oxide PCC, pyridinium chlorochromate Ph, phenyl PMB, / -methoxvbenzyl PPTs, pyridiniump-toluenesulfonate i-Pr, isopropyl Py, pyridine rt, room temperature TBAF, tetrabutylammonium fluoride TBS, ferf-butyl dimethylsilyl TBDMSC1, f-butylchlorodimethylsilane Tf, trifhioromethylsulfonyl Tf20, trifluoromethylsulfonic anhydride TFA, trifluoroacetic acid THF, tetrahydrofuran TMS, trimethylsilyl TPAP, tetra-n-propylammonium perruthenate / -TsOH. / -toluenesulfonic acid... 

FIGURE 8.8 Magnetic field dependence for the photolysis of a series of benzoyl containing molecules in cyclohexanol solution obtained by time-resolved infrared spectroscopy of the carbonyl group of the resulting benzoyl radical. Key 1 = a,a,a-trimethylacetophenone, 2 = 2-hydroxy-4-(2-hydroxyethoxy)-2-methylpropiophenone, 3 = 1-benzoylcyclohexanol, 4 = 2-hydroxy-2-methy Ipropiophenone, 5 = benzoin, 6 = methyl ether benzoin, 7 = dimethyl ether benzoin, 8 = 2-dimethylamino-2-(4-methyl-benzyl)-l-(4-morpholin-4-yl-phenyl)-butan-l-one. 

Benzyl-4,4,5,5-tetramcthyl-l,3-dioxolan-2-enium-tetrafluoroborat5l Zu 0,6 g (5 mmol) 2,3-Dimethyl-2,3-butandiol und 1,55 g (10 mmol) Phenyl-essigsaurc-chlorid in 5 ml absol. Chloroform gibt man tropfenweise 1,2 ml Bortrifluorid-Diethylctherat, erwarmt 1 -2 Min. auf 80° und verdiinnt mit absol. Ether. Man saugt ab und wascht mit absol. Ether Ausbcute 1,18 g (78%). 

Interestingly, the stereochemical outcome in the reaction of a-Hthiated benzyl phenyl sulfide is different from that in the reaction of a-hthiated benzyl methyl ether which proceeds through a dynamic thermodynamic resolution pathway [Eq. (7)] [15,43]. Taking account of Wiberg s results, namely, that the a-oxy carbanion of dimethyl ether places the lone pair of carbanion syn to the methyl group by the electron repulsive effect [25], the difference in the stereochemical outcome between a-thio and a-oxy carbanions would be ascribed to their different preferred conformations. A similar change in the stereochemical outcome has been observed in reactions of dipole-stabilized a-thio and a-oxy organoUth-ium compound, as shown in Eqs. (4) and (5). 

At high temperatures (140-180 °C), dibenzylcarbonate (DBzlC) is an efficient benzylating agent of phenol and methylene acidic compounds, such as phenylacetonitrile and benzyl phenylacetate (77). At reflux temperature in N,N-dimethyl-formamide (DMF) solvent with KjCOs as the catalyst, DBzlC react with phenol to yield the benzyl phenyl ether (Eq. 9). Phenylacetonitrile yields the monobenzylated compound (2,3-diphenyl-propionitrile) (Eq. 10). 

Phenyl-2-methyl-2-propanol. See Dimethyl benzyl carbinol 3-Phenyl-2-methyl-propen-2-ol-1. See Methylcinnamyl alcohol 1 -Phenyl-3-methyl-5-pyrazolone CAS 89-25-8 EINECS/ELINCS 201-891-0 Synonyms Cl developer 1 Developer Z 2.4-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one 3-Methyl-1 -phenyl-2-pyrazolin-5-one 3-Methyl-1 -phenyl-5-pyrazolone Norantipyrine Norphenazone 1-Phenyl-3-methyl-5-oxo-2-pyrazoline 1-Phenyl-3-methylpyrazolone-5 5-Pyrazolin-5-one, 3-methyl-1-phenyl-5-Pyrazolone, 3-methyl-1-phenyl-Empirical C10H10N2O Formula C6HsNN C(CH3)CH2CO Properties Wh. to It. yel. powd. orcryst. sol. 10-50 mg/ml in DMSO, 95% ethanol, acetone si. sol. in benzene sol. < 1 mg/ml in water insol. in ether, petrol, ether m.w. 174.20 vapor pressure < 0.01 mm Hg (20 C) m.p. 127-130 C b.p. 287 C (105 mm) ref. index 1.637 (20 C)... 

Acetone Amyl formate Benzaldehyde Benzene Benzonitrile Benzyl acetate Bromodichloromethane 2-Butanol Butoxyethanol acetate 1-Butoxyethoxy-2-propanol Butyl alcohol p-t-Butyl toluene Cyclohexane Cyclohexyl acetate Decahydronaphthalene Dibutyl phthalate cis-1,2-Dichloroethylene Diethyl carbonate Diethylene glycol phenyl ether Diethylenetriamine Diethyl oxalaU Diethyl tartrate Diethyl toluamide Dimethyl acetamide Dimethyl adipate... 

A, A, iV ,A -tetramethylethylenediamine (TMEDA) and A,A,A ,iV -tetramethyl-methylenediamine are treated with 5ec-butyllithium or tert-butyllithium. n-Butylpotassium converts dimethyl ether readily to methoxymethylpotassiumJ Ethyl and methyl vinyl ether require sec- or rm-butyllithium to undergo a-metalation, whereas n-butyllithium suffices to bring about the or// o-lithiation of anisole and the a-lithiation (at the oxygen-adjacent position) of allyl phenyl ether and benzyl phenyl ether. 

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