- Intramolecular activation of imidate with cationic gold(I) catalyst: A new benzylation reaction of alcohols
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Benzylation of alcohols with benzyl (Z)-2,2,2-trifluoro-N-(2-alkynylphenyl)acetimidates 5a-f in the presence of a cationic gold(I) catalyst was investigated. Reagent 5f was the most effective, affording benzyl ethers in good yields. Our results indicate that these gold(I)-activated imidates are effective leaving groups.
- Ban, Shintaro,Endo, Tomotake,Matsui, Rikako,Morita, Nobuyoshi,Hashimoto, Yoshimitsu,Tanaka, Kosaku,Tamura, Osamu
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- A method of manufacturing an alkylene glycol ether (poly)
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PROBLEM TO BE SOLVED: To provide a method for producing a (poly)alkylene glycol diether, introducing the oxyalkylene groups of the optional mole number of addition and optional terminal alkyl groups by using a metallosilicate catalyst having 10 to 1,000 ratio of SiO2/M2O3as an ether interchange reaction catalyst. SOLUTION: This method for producing the (poly)alkylene glycol diether includes a process of obtaining the (poly)alkylene glycol diether by the ether interchange reaction of a first (poly)alkylene glycol monoether with a second (poly)alkylene glycol monoether in the presence of the metallosilicate catalyst having 10 to 1,000 ratio of SiO2/M2O3(wherein, M is ≥1 kind selected from the group consisting of Al, Ga, Ge, B, Zn, P, Zr, Ti, Cr, Be, V and As). COPYRIGHT: (C)2012,JPOandINPIT
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Paragraph 0056; 0057
(2016/10/17)
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- Ferric perchlorate as an efficient and useful catalyst for the selective benzylation and methylation of alcohols with benzyl chloride and methyl iodide
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A mild and efficient method was developed for selective benzylation and methylation of hydroxyl compounds in the presence of a catalytic amount of ferric perchlorate. We showed that ferric perchlorate was very effective in selectively promoting the benzylation and methylation of primary aliphatic and benzylic alcohols versus secondary aliphatic alcohols and phenolic hydroxy groups. Graphical abstract: [Figure not available: see fulltext.]
- Behbahani, Farahnaz K.,Heravi, Majid M.,Oskooie, Hossien A.
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experimental part
p. 181 - 184
(2010/03/26)
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- Benzylation of alcohols by using bis[acetylacetonato]copper as catalyst
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Selective O-benzylation of primary hydroxy compounds has been achieved in the presence of bis[acetylacetonato]copper with benzyl chloride. We showed that bis[acetylacetonato]copper was very efficient in promoting the benzylation of primary aliphatic alcohols versus secondary aliphatic alcohols and phenolic hydroxy groups selectively.
- Sirkecioglu, Okan,Karliga, Bekir,Talinli, Naciye
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p. 8483 - 8485
(2007/10/03)
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- Intramolecular benzyl-benzyl interactions in protonated benzyl diethers in the gas phase. Effects of internal hydrogen bonding
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Protonated molecules of a variety of benzyl diethers, produced by chemical ionization (CI), undergo a unique rearrangement yielding relatively abundant mlz 181 C14H13+ ions, both in the ion source and under collision-induc
- Edelson-Averbukh, Marina,Etinger, Alexander,Mandelbaum, Asher
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p. 1095 - 1105
(2007/10/03)
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- Highly selective Silver(I) oxide mediated monoprotection of symmetrical diols
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Treatment of symmetrical diol with Ag2O and alkyl halide gave the monoprotected derivative in good to excellent yield.
- Bouzide, Abderrahim,Sauve, Gilles
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p. 5945 - 5948
(2007/10/03)
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- Monobenzylation of 1,n-diols via dibutylstannylene intermediates
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Symmetrical primary 1,n-diols, HO(CH2)(n)OH, of any chain length from n = 2-10, can be selectively monobenzylated via sequential treatment with dibutyltin oxide and benzyl bromide.
- Mash, Eugene A.,Kantor, Liza T. A.,Waller, Stephen C.
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p. 507 - 514
(2007/10/03)
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- Regioselective De-O-benzylation with Lewis Acids
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Simple and highly regioselective de-O-benzylations of poly-O-benzylated monosaccharides and polyols with Lewis acids (SnCl4 and TiCl4) were developed.Spectral studies on intermediates complexes showed that three appropriately situated metal chelating functional groups were necessary for the selective de-O-benzylation.
- Hori, Hiroshi,Nishida, Yoshihiro,Ohrui, Hiroshi,Meguro, Hiroshi
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p. 1346 - 1353
(2007/10/02)
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- SELECTIVE MONOETHERIFICATION AND MONOESTERIFICATION OF DIOLS AND DIACIDS UNDER PHASE-TRANSFER CONDITIONS
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Research on the selectivity of etherification reactions of diols and esterification reactions of diacids by alkyl halides under phase-transfer catalysis has shown that under such conditions, selectivity of monoetherification increases in the order prim sec tert diols, though overall yield of monoether decreases from sec to tert diols.Monoesterification of diacids was accomplished with a high degree of selectivity.Optimal extraction of diols and diacids was found to correspond in general to chain lengths of around 5 carbons.This could mean that the complex formed between the catalyst and the anion to react is stabilized for certain carbon lengths by inner solvation in virtue of its spatial conformation.
- Zerda, Jaime de la,Barak, Gabriela,Sasson, Yoel
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p. 1533 - 1536
(2007/10/02)
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- Veretherungen von Diolen, Triolen und Hydroxycarbonsaeurederivaten ueber Thallium(I)-alkoholate. Eine neue Variante der Williamson-Reaktion
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The etherifications listed in tables 1 and 2 are achieved by converting hydroxy-derivatives, which contain additional oxygen functions, into thallium(I) alkoxides with thallium ethoxide, and treatment with haloalkanes.The scope and limitations of the method are discussed.
- Kalinowski, Hans-Otto,Crass, Gerhard,Seebach, Dieter
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p. 477 - 487
(2007/10/02)
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- Group IB organometallic chemistry. XIV. Intramolecular ring-closure reactions of novel arylcopper compounds RCuI2. Synthesis of 7,8-dihydrodibenzo[f,h][1,4]dioxecin and 7,8-dihydrodibenzo-6,9-dimethyl[f,h][1,4]diazecin
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The reaction of 1,2-bis{N-[2-(bromomagnesio)benzyl]-N-methylamino}ethane (III) with CuCl2 results in the formation of 1,2-bis[N-(2-cupriobenzyl)N-methylamino] ethane (I, 2,2′-Cu2RN) and of the product of intramolecular ring-closure 7,8-dihydrodibenzo-6,9-dimethyl[f,h][1,4]diazecin (VII). The formation of 2,2′-RN (VII) is explained in terms of a concerted electron-transfer/CC coupling reaction within a complex of the monomagnesium species 2,2′-MgRN (VIII) with CuCl2. Molecular weight determinations and NMR spectroscopic data for I point to a tetranuclear structure (2,2′-Cu2RN)2 in which (2,2′-Cu2RN)2 in which the two multicenter-bonded aryl groups in each of the RN ligands are arranged in a trans-manner. This structure accounts for the exclusive formation of 2,2′-RN (VII) upon thermal decomposition of I. The interaction of 1,2-bis[2-(bromomagnesio)benzyloxy] ethane (X) with CuCl2 affords the ring-closed product 7,8-dihydrodibenzo[f,h][1,4] dioxecin (IX) in addition to the organodicopper XII. Thermal decomposition of XII yields 2,2′-RO (IX) quantitatively.
- van Koten, Gerard,Noltes, Jan G.
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p. 127 - 138
(2007/10/06)
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