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1.
Alexander D Dilman Pavel A Belyakov Vladimir A Tartakovsky 《Tetrahedron letters》2004,45(19):3741-3744
Silyl enol ethers bearing three pentafluorophenyl groups at the silicon atom are described. These compounds undergo uncatalyzed aldol reactions with aliphatic, α,β-unsaturated, and aromatic aldehydes. The observed reactivity is analyzed in terms of the Lewis acidity of the silyl fragment. 相似文献
2.
Alexander D. Dilman Dmitry E. Arkhipov Valentine P. Ananikov Vladimir A. Tartakovsky 《Journal of organometallic chemistry》2005,690(16):3680-3689
A general method for the synthesis of carbon-centered tris(pentafluorophenyl)silyl derivatives (RSi(C6F5)3) by reaction of trichlorosilanes (RSiCl3) with pentafluorophenylmagnesium bromide was described. The crystal structures of obtained compounds were studied by X-ray diffraction analysis (7 structures). The peculiarities of crystal packing were analyzed by means of DFT calculations. 相似文献
3.
A. D. Dilman D. E. Arkhipov P. A. Belyakov M. I. Struchkova V. A. Tartakovsky 《Russian Chemical Bulletin》2006,55(3):517-522
Reactions of tris(pentafluorophenyl)silanes RSi(C6F5)3 with salicylaldehyde and secondary amines were studied. The reactions afforded α-pentafluorophenyl-substituted amines. Silanes
RSi(C6F5)3 (R = Me, Ph, C6F5, CH2CH=CH2, and CH=CH2) were found to be efficient reagents for transfer of the C6F5 group to the iminium cation generated from salicylaldehyde and amine. However, tris(pentafluorophenyl)phenylethynyl-and tris(pentafluorophenyl)silanes
were not able to serve as a source of a fluorinated substituent because of competitive transfer of acetylenide fragment or
hydride.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 498–503, March, 2006. 相似文献
4.
Dilman AD Belyakov PA Korlyukov AA Struchkova MI Tartakovsky VA 《Organic letters》2005,7(14):2913-2915
[reaction: see text] The three-component coupling of aldehydes, secondary amines, and methoxytris(pentafluorophenyl)silane, MeOSi(C(6)F(5))(3), affording pentafluorophenylmethylamines has been described. The generation of the five-coordinate silicate intermediate is believed to be the key feature responsible for the efficiency of the reaction. 相似文献
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I. Yu. Chernyshov V. V. Levin A. D. Dilman P. A. Belyakov M. I. Struchkova V. A. Tartakovsky 《Russian Chemical Bulletin》2010,59(11):2102-2107
A three-step method for the preparation of CF3-substituted 1,2,3,4-tetrahydroisoquino-lines and 1,2,3,6-tetrahydropyridines has been suggested. The first step includes
alkylation of isoquinoline or 4-methylpyridine at the nitrogen atom with the formation of salts, which are involved into the
reaction with Grignard reagent or lithium triethylborohydride to give enamines. The enamines undergo nucleophilic trifluoromethylation
upon the action of Me3SiCF3 under acidic conditions. 相似文献
8.
Liubov I. Panferova Grigory N. Chernov Vitalij V. Levin Vladimir A. Kokorekin Alexander D. Dilman 《Tetrahedron》2018,74(50):7136-7142
A method for the synthesis of 3,3-difluorotetrahydrofurans from iododifluoromethylated alcohols and 1,1-diarylethylenes is described. The reaction is performed under irradiation with 400?nm light emitting diodes in the presence of a cationic iridium(III) photocatalyst, [Ir(ppy)2(dtbbpy)]PF6, substoichiometric amounts of triphenylphosphine and sodium trifluoroacetate as a base. 相似文献
9.
Alexander D. Dilman Vitalij V. Levin Pavel A. Belyakov Mikhail Yu. Antipin 《Journal of organometallic chemistry》2008,693(6):1005-1019
A detailed analysis of monodentate and bidentate complexation of tris(pentafluorophenyl)silyl (TPFS) derivatives with neutral Lewis bases was performed. The NMR spectroscopy and X-ray diffraction analysis (11 structures) were the key methods to characterize tetra- or pentacoordinate silicon compounds, whereas the peculiarities of crystal packing were analyzed by means of DFT calculations. The interaction of TPFS-X (X = F, Cl, OTf) with strong Lewis bases (HMPA, N-methylpyrrolidinone) may afford three different species: neutral pentacoordinate TPFS(X)-L, cationic tetracoordinate TPFS-L+ X−, and cationic pentacoordinate TPFS-(L)+2X−, representatives of each type were characterized by X-ray diffraction. A variety of complexes with bidentate complexation, featuring the trigonal bipyramidal geometry with apical C6F5-group was prepared and structurally characterized. The extent of Si-Capical bond elongation depends on the donating ability of the coordinating ligand, with the longest Si-C bond of 1.981(1) Å observed for six-membered complex of TPFS-ether of N-(2-hydroxybenzoyl)pyrrolidine. 相似文献
10.
Kunetsky RA Dilman AD Ioffe SL Struchkova MI Strelenko YA Tartakovsky VA 《Organic letters》2003,5(25):4907-4909
A strategy for the synthesis of isoxazoline-N-oxides (cyclic five-membered nitronates) from primary nitro compounds and olefins is described. The key step of the process involves 1,3-dipolar cycloaddition of corresponding 1-bromosilyl nitronates with alkenes. [reaction: see text] 相似文献