R 30 Reaction of 2-polyfluoroacylcyclohexanones with semicarbazides [Electronic resource] / K. I. Pashkevich, D. V. Sevenard, O. G. Khomutov, O. V. Shishkin, E. V. Solomovich // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1999. - Vol. 48, N 2. - P359-363 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1999, 48 (2), 359-363.pdf |
P 80 Polyfunctional Fluoroalkyl Carbonyl Compounds as Building Blocks for Synthesis of Heterocycles [Text] : доклад, тезисы доклада / K. I. Pashkevich, V. I. Filyakova, V. G. Ratner, O. G. Khomutov, O. A. Kuznetsova, D. V. Sevenard // International Memorial I.Postovsky Conference on Organic Chemisty, Ekaterinburg, March 17-20, 1998 : program and abstracts. - Ekaterinburg, 1998. - P107 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 51 Sevenard, D. V. Interaction of 2-polyfluoroalkyl Cyclalkanones with Hydroxylamine and Hydrazines [Text] : доклад, тезисы доклада / D. V. Sevenard, O. G. Khomutov, K. I. Pashkevich // International Memorial I.Postovsky Conference on Organic Chemisty, Ekaterinburg, March 17-20, 1998 : program and abstracts. - Ekaterinburg, 1998. - P119 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 98 Synthesis of trifluoroalkyl- and fluoroaryl-substituted 4,5-dihydro-1H-1,2,4-triazole-5-thiones [Electronic resource] / E. B. Vasil'eva, D. V. Sevenard, O. G. Khomutov, O. A. Kuznetsova, N. S. Karpenko, V. I. Filyakova // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2004. - Vol. 40, № 6. - P874-878. - Библиогр. : с. 878 (8 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 4-(4-fluorophenyl)-, 4-(4-trifluoromethoxyphenyl)-, 4-(3,4-difluorophenyl)-, 4-(4-trifluoromethylphenyl)-, 4-piperidino-, and 4-(3-pyridyl)thiosemicarbazides with esters gave the corresponding 3,4-disubstituted 4,5-dihydro-1H-1,2,4-triazole-5-thiones and their S-alkyl derivatives. Analogous reactions with methyl 2,2,3,3,4,4,5,5-octafluoropentanoate and 2,2,3,3,4,4,5,5-octafluoropentanenitrile afforded, respectively, the acylation and addition products. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2004, 40 (6), 874.pdf |
A 77 Aromatization via a dibromination-double dehydrobromination sequence: a facile and convenient synthetic route to 2,6-bis(trifluoroacetyl)phenols [Text] / D. V. Sevenard, O. Kazakova, R. -M. Schoth, E. Lork, D. L. Chizhov, J. Poveleit, G. -V. Roeschenthaler // Synthesis. - 2008. - № 12. - P1867-1878 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\expert2\\nbo\\Synthesis\\2008, № 12. р.1867.pdf |
T 44 The structure of 4-phenyl-2,6-bis(trifluoroacetyl)cyclohexanone and its dilithium salt in the crystal state, solution and gas phase [Electronic resource] / D. V. Sevenard, O. Kazakova, E. Lork, T. Duelcks, D. L. Chizhov, G. -V. Roeschenthaler // Journal of Molecular Structure. - 2007. - Vol. 846, № 1-3. - P87-96 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 4-Phenyl-2,6-bis(trifluoroacetyl)cyclohexanone and its dilithium salt were synthesized starting from the commercially available 4-phenylcyclohexanone. With X-ray structure analysis of these compounds, for the first time the solid state structure determination for a fluorinated 1,3,5-triketone and an alkaline salt of 1,3,5-triketone was achieved. The subsequent multinuclear NMR and MS investigations revealed that in solution and gas phase, analogously to the crystal, both compounds exist predominantly in a highly delocalized double U-enol(ate) form. The carbonyl O…O distances in the dilithium salt were established to be considerably longer than the distances between oxygens of the parent 1,3,5-triketone, bonded by strong (short) resonance assisted hydrogen bonds. Among the 1,3,5-tricarbonyl compounds with known crystal structure, the entitled 1,3,5-triketone shows comparatively weak delocalization over the conjugated bis-enolone backbone. \\\\Expert2\\nbo\\Journal of Molecular Structure\\2007, v.846, p.87.pdf |
H 19 Halogenation of fluorinated 1,3,5-triketones [Text] / D. V. Sevenard, O. Kazakova, D. L. Chizhov, D. S. Yachevskii, E. Lork, J. Poveleit, V. N. Charushin, G. -V. Roeschenthaler // Helvetica Chimica Acta. - 2007. - Vol. 90, № 2. - P369-384. - Библиогр. : с. 384 (17 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The behavior of linear and cyclic fluorinated 1,3,5-triketones and their metal derivatives towards common halogenating agents was examined, and optimal reaction conditions for the straightforward synthesis of mono-, di-, and tetrahalogenated products were found (Schemes 1-3). An aromatization through a double HBr elimination from an ,-dibrominated cyclohexanone was shown to be a promising synthetic route to 1,1-(2-hydroxy-1,3-phenylene)bis[2,2,2-trifluoroethanones] (= 2,6-bis(trifluoroacetyl)phenols; Scheme 4). Additionally, the 1,3,5-triketones prepared add readily H2O or alcohols to produce novel bridged 2,6-dihydroxypyran-4-ones (Scheme 2). The structure of the obtained compounds 6a and 7a was confirmed by X-ray structure analysis. |
F 70 Fluorinated Pd(II)-1,3,5-triketonates: synthesis and molecular structure [Text] / D. L. Chizhov, D. V. Sevenard, E. Lork, K. I. Pashkevich, G. -V. Roeschenthaler // Journal of Fluorine Chemistry. - 2004. - Vol. 125, № 7. - P1137-1141 : ил. - Библиогр.: с. 1141 (20 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): POLYFLUOROALKYLATED 1,3,5-TRIKETONES -- 2-PERFLUOROHEPTANOYL CYCLOHEXANONE -- MONONUCLEAR PD(II) TRIKETONATES -- ENOLIZATION -- MOLECULAR STRUCTURE -- X-RAY ANALYSIS Аннотация: Several new mononuclear complexes of Pd(II) have been prepared from perfluorobutyl substituted 1,3,5-triketones (containing linear and carbocycle backbones) and perfluoroheptanoyl cyclohexanone. 1,3-Diketones formed a mixture of trans- and cis-forms, whereas 1,3,5-triketones gave trans-complexes exclusively. The enolization of the non-bonded carbonyls in this case depends on the nature of substituents at positions 2 and 4 of the 1,3,5-triketone moiety. The molecular structure of one triketonate complex was confirmed by X-ray single crystal investigation.???? \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2004, v.125, p.1137.pdf |
S 98 Syntheses of novel 4-polyfluoroalkyl-substituted 5,6-oligomethylene pyrimidines [Text] / D. V. Sevenard, O. G. Khomutov, O. V. Koryakova, V. V. Sattarova, M. I. Kodess, J. Stelten, I. Loop, E. Lork, K. I. Pashkevich, G. -V. Roeschenthaler // Synthesis. - 2000. - № 12. - P1738-1748 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 2-Acylcycloalkanones having polyfluoroalkyl groups react with guanidine, urea, thiourea, methylisothiourea, benzamidine, guanylthiourea, dicyanodiamide, and trifluoroacetylurea by Lewis-acid catalysis to form the corresponding 5,6-oligomethylene pyrimidines. A decrease in the yields along with increase of polyflyoroalkyl substituent length in the molecule of the starting 1,3-diketone was observed in the case of reagents with lower nucleophilicity (urea, thiourea, dicyanodiamide). The pyrimidines obtained from aromatic aldehydes showed E-configuration with respect to the arylidene double bond. Tautomeric structures as a function of the substituent in 2 position in the pyrimidine ring both in liquid and solid state were investigated by X-ray diffraction, IR and NMR spectroscopy. \\\\expert2\\nbo\\Synthesis\\2000, № 12. p.1738.pdf |
N 89 Novel polyfluoroalkylated pyrazoles from 2-polyfluoroacylcycloalkanones and hydrazines: Syntheses and unequivocal molecular structure assignment [Text] / D. V. Sevenard, O. G. Khomutov, M. I. Kodess, K. I. Pashkevich, I. Loop, E. Lork, G. -V. Roeschenthaler // Canadian Journal of Chemistry. - 2001. - Vol. 79, № 2. - P183-194 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HYDRAZINES -- MOLECULAR STRUCTURE -- ISOMERIC PYRAZOLES; Аннотация: The reaction between 2-trifluoroacetylcycloalkanones and methylhydrazine or phenylhydrazine exclusively yields 3-CF3-pyrazoles. When the chain length of the polyfluorinated substituent in RFC(O) group increases, 5-RF-pyrazoles are isolated. The reaction of 2-trifluoroacetylcyclohexanone with 2-hydrazinopyradine gives 5-hydroxypyrazoline, an intermediate in the formation of 5-CF3-pyrazoles. The regiochemistry of the condensation is probably controlled by the nucleophilicity of the terminal nitrogen in the mono substituted hydrazines and by the steric requirements of the RF group in the 1,3-diketones. Polymethylene chain containing pyrazoles obtained from the 1,3-diketones in question and hydrazine prefer the 3-RF tautomeric form, irrespective of carbocyclic ring size and polyfluoroalkyl group chain length. |
C 73 Condensation of 2-polyfluoroacycloalkanones with aldehydes and dimethylformamide-dimethylacetal [Text] / D. V. Sevenard, O. G. Khomutov, M. I. Kodess, K. I. Pashkevich, I. Loop, E. Lork, G. -V. Roeschenthaler // Australian Journal of Chemistry. - 2001. - Vol. 54, № 3. - P157-163 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Polyfluorinated 1,3-diketones containing carbocycles react with aldehydes under Lewis-acid catalysis and also with dimethylformamide-dimetylacetal without catalysis, yielding exclusively (E)-configured condensation products involving the methylene group of the carbocycle. Novel trifluoromethylated chromenes are prepared from 2-trifluoroacetylcycloalkanones and salicylaldehyde. The structures of two new compounds, 2-(E)-benzylidene-6-trifluoroacetylcyclohexanone and 4-trifluoroacetyl-2,3-dihydro-1H-xantene, are confirmed by X-ray structure analysis. |
S 98 Synthesis of 1,1,1,7,7,7-hexafluoroheptane-2,4,6-trione, the simplest fluorinated 1,3,5-triketone [Text] / D. V. Sevenard, O. Kazakova, D. L. Chizhov, G. -V. Roeschenthaler // Journal of Fluorine Chemistry. - 2006. - Vol. 127, № 7. - P983-986 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A simple, convenient and effective method to synthesize 1,1,1,7,7,7-hexafluoroheptane-2,4,6-trione, the simplest fluorinated 1,3,5-triketone, on a preparative scale was developed. The title compound was obtained by a Claisen-type double condensation of acetone with trifluoroacetic acid ethyl ester and isolated as a solid monohydrate from the reaction mixture. Subsequent dehydration proceeds smoothly to produce the desired compound as an individual substance. Its peculiar tautomeric (keto–enol, ring–chain) features in various solvents are discussed \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2006, v.127, p.983.pdf |
M 61 Metal and boron derivatives of fluorinated cyclic 1,3-dicarbonyl compounds [Text] / D. V. Sevenard, O. G. Khomutov, N. S. Boltacheva, V. I. Filyakova, V. Vogel, V. Ya. Sosnovskikh, V. O. Iaroshenko, G. -V. Roeschenthaler // Zeitschrift fur Naturforschung - Section B. Journal of Chemical Science. - 2009. - Vol. 64, № 5. - P541-550 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Starting from the corresponding cyclic 1,3-diketones or other precursors (cyclic ketones as well as lactones), several new salts and chelate complexes of fluorinated 1,3-dicarbonyls were obtained. Their preparative significance was demonstrated by straightforward syntheses of fluorinated pyrazoles, benzimidazoles and 1,7-ketoesters. The structure of a boron chelate of 2-(trifluoroacetyl)- cyclohexanone was investigated by X-ray diffraction |
F 26 Fast Enol-enol Tautomerism of Fluorinated 1,3-Dicarbonyl and 1,3.5-Tricarbonyl Compounds Reinvestigated [Text] : доклад, тезисы доклада / D. V. Sevenard, G. -V. Roeschenthaler, I. I. Bilkis, M. I. Kodess, D. L. Chizhov, K. I. Pashkevich, D. V. Sevenard // 18th ISFC international Symposium on Fluorine Chemistry. Bremen, 30th Jul.-4 Aug. 2006 г. : Final Program. Abstracts. - Bremen, 2006. - P180 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ENOL-ENOL -- TAUTOMERISM -- TRICARBONY |
H 19 Halogenation of Fluorinated 1,3-Dicarbonyl and 1,3,5-Tricarbonyl Compounds [Text] : доклад, тезисы доклада / D. V. Sevenard [и др.] // 18th ISFC international Symposium on Fluorine Chemistry. Bremen, 30th Jul.-4 Aug. 2006 г. : Final Program. Abstracts. - Bremen, 2006. - P271 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HALOGEN -- HALOGENATION AGENTS |
S 98 Synthesis and tautomeric equilibrium of 2,6-bis(trifluoroacetyl)cyclohexanone [Electronic resource] / D. V. Sevenard, O. G. Khomutov, M. I. Kodess, K. I. Pashkevich // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1999. - Vol. 48, № 2. - P400-401 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1999, 48 (2), 400.pdf |
R 30 Reaction of 2-(polyfluoroacyl)cycloalkanones with hydroxylamine [Text] / D. V. Sevenard, O. G. Khomutov, K. I. Pashkevich, E. Lork, G. -V. Roeschenthaler // Helvetica Chimica Acta. - 2002. - Т. 85, № 7. - P1960-1972. - Библиогр.: с. Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The 2-acylcycloalkanones 1a-g and 3a-c, possessing a polyfluoroalkyl group, react with hydroxylamine regio- and stereoselectively to yield 4,5-dihydroisoxazol-5-ols 2a-g and 4a-c, respectively, i.e., products of N-addition to the oxo group at the cycloalkane ring (Schemes 1 and 2). The products 2 and 4 can be dehydrated under drastic conditions only (Schemes 3 and 4). The structure of one of the 4,5-dihydroisoxazol-5-ols was confirmed by X-ray crystal-structure analysis |
R 18 Ralph-Matthias Schoth Fluorinated 1,3-diketones, 2-trifluoroacetyl phenols and their derivatives: versatile reactants in phosphorus chemistry [Text] / Ralph-Matthias Schoth , D. V. Sevenard, K. I. Pashkevich // Coordination Chemistry Reviews . - 2000. - Vol. 210, № 1. - P101-134 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
R 30 Reactions of fluoroalkyl-containing lithium 1,3-diketonates with diaminoarenes and 2-aminobenzenethiol [Electronic resource] / V. I. Filyakova, N. S. Boltacheva, D. V. Sevenard, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2010. - Vol. 59, № 9. - P1791-1796. - Bibliogr. : p. 1796 (25 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): FLUOROALKYL -- CONTAINING LITHIUM 1,3-DIKETONATES -- 1,2-DIAMINOBENZENE -- 2,3-DIAMINONAPHTHALENE -- 1,2-DIAMINO-4,5-DIFLUOROBENZENE -- 2-AMINOBENZENETHIOL Аннотация: 1,5-Benzo[b]- and 1,5-naphtho[2,3-b]diazepines were synthesized by the reaction of lithium 1,3-diketonates with 1,2-diaminobenzene and 2,3-diaminonaphthalene in an MeOH-AcOH-HCl mixture at 0 °C. The reactions of fluoroalkyl-containing lithium 1,3-diketonates with 1,2-diaminobenzene and 1,2-diamino-4,5-difluorobenzene under reflux in acetic acid afford 2-fluoroalkyl-containing benzimidazoles as the major products, whereas the reaction with 2-aminothiophenol gives 2-phenylbenzothiazole. The reactions of lithium diketonate containing the cyclohexane and cyclopentane moieties with 1,2-diaminoarenes and 2-aminobenzenethiol are accompanied by the opening of the carbocycle to form 2-(6-oxo-7,7,7-trifluoroheptyl)benzimidazole and 2-(5-oxo-6,6,6-trifluorohexyl)benzothiazole hydrates, respectively. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2010, 59 (9), 1791-1796.pdf |