Diphenylmethyl ethers

This group was developed for protection of the 5 -OH group in nucleosides. The derivative is prepared from the corresponding triaiylmethyl chloride, and is cleaved by reductive cleavage (Zn/AcOH) of the phenacyl ether to the p-hydroxyphenyl-diphenylmethyl ether followed by acidic hydrolysis with formic acid. ... 

MMTr Sodium naphthalenide in HMPA (90% yield)/ The MMTr group is not cleaved by sodium anthracenide, used to cleave O -naphthyl-diphenylmethyl ethers. ... 

A. BotMs, 1. Hajkb, M. Kajtdr-Heaedy, and A. Liprik, Hydrogenolyris of dro ol nr-type diphenylmethylene acetals by AlCIHj to axial diphenylmethyl ethers, J. Carbokydr. Chem. 12 191 (1993) and references therein. 

A completely different course of reaction was established when one or both benzylic protons in the benzyl alcohol molecule were replaced with phenyl or methyl substituents diphenyl methanol gives bis(diphenylmethyl) ether, while 2-phenyl-2-propanol was transformed to 2,4-diphenyl-4-methyl-l-pentene)106 (Scheme 40). 

Synonyms. Benztropine Methanesulphonate Tropine Diphenylmethyl Ether. 

Tropanyl mandelate, 660 Tropanyl tropate, 363 Tropanyl ( -tropate, 676 Tropic acid, 364 Tropicamide, 1054 Tropine, xvii, 364 Tropine diphenylmethyl ether, 388 Tropium, 446... 

The behavior of arylmethanols towards anhydrous hydrogen fluoride is very specific. In cases where dehydration is possible yields are usually low or the fluorinated products are unstable. Diphenylmethanol, which cannot lose water, gives only bis(diphenylmethyl) ether (78 % yield) upon treatment with anhydrous hydrogen fluoride at low temperature. However, good to excellent yields of fluorides 3 are obtained from highly halogenaled arylmethanols and (nitro-aryl)methanols. 

DIFENHYDRAMIN DIFENIDRAMINA (ITALIAN) DIHIDRAL DIMEDROL DIMEDRYL fi-DIMETHYLAMINO-AETHYL-BENZHYDRYL-AETHER (GERMAN) P-DIMETHYLAMINOETHANOL DIPHENYLMETHYL ETHER a-(2-DIMETHYLAMINO-ETHOXY)DIPHENYLMETHANE P-DIMETHYL-AADNOETHYLBENZHYDRYLETHER DIPHANTINE... 

DIMETHYLAMINO)ETHANOL see DOY800 N-DIMETHYLAMINOETHANOL see DOY 800 N,N-DIMETHYLAXnNOETHANOL see DOY800 p-DIMETHYLAMINOETHANOL see DOY800 p-DIMETHYIAMINOETHxWOL DIPHENYLMETHYL ETHER see BBV500... 

Photolysis of 3-thietanone involves both singlet and triplet excited states the initial products are sulfene and ketene, as determined by IR spectroscopy at liquid nitrogen temperatures in a pentane matrix.When the photolysis is done in methanol, isopropyl alcohol, or r-butyl alcohol, these intermediates are trapped as the acetate and methanesulfonate esters. In diphenylmethanol solvent, the bis-diphenylmethyl ether is formed by displacement of the alcohol on the sulfonate ester. Photolysis of tetramethyl-3-thietanone 1,1-dioxide gives dimethylketene. ... 

Tetraphenylcyclopropane (1), when irradiated (254 nm), produced 1,1-diphenylethene (2) and diphenylcarbene (3), which was subsequently trapped with methanol to yield methyl diphenylmethyl ether (4). ... 

The a-naphthyldiphenylmethyl ether was prepared to protect, selectively, the 5-OH group in nucleosides. It is prepared from a-naphthyldiphenylmethyl chloride in pyridine (65% yield) and cleaved selectively in the presence of a p-methoxyphenyl-diphenylmethyl ether with sodium anthracenide, a (THF, 97%, yield). The p-me-thoxyphenyldiphenylmethyl ether can he cleaved with acid in the presence of this group. ... 

Stereoselective cleavage of dipk diphenylmethyl ethers of pyranosides available equatorial oxygen atom pi results. 

Stereoselective cleavage of diphenylmethylene acetals. Formation of axial diphenylmethyl ethers of pyranosides is noted. Preferential coordination to the more available equatorial oxygen atom prior to the hydride delivery may explain the results. 

Triethylsilane can also facilitate the high yielding reductive formation of dialkyl ethers from carbonyls and silyl ethers. For example, the combination of 4-bromobenzaldehyde, trimethylsi-lyl protected benzyl alcohol, and EtsSiH in the presence of catalytic amounts of FeCls will result in the reduction and benzylation of the carbonyl group (eq 32). Similarly, Cu(OTf)2 has been shown to aid EtsSiH in the reductive etherification of variety of carbonyl compounds with w-octyl trimethylsilyl ether to give the alkyl ethers in moderate to good yields. Likewise, TMSOTf catalyzes the conversion of tetrahydrop)ranyl ethers to benzyl ethers with Ets SiH and benzaldehyde, and diphenylmethyl ethers with EtsSiH and diphenylmethyl formate. Symmetrical and unsymmetrical ethers are afforded in good yield from carbonyl compounds with silyl ethers (or alcohols) and EtsSiH catalyzed by bismuth trihalide salts. An intramolecular version of this procedure has been nicely applied to the construction of cA-2,6-di- and trisubstituted tetrahydropyrans. ... 

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