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1.
T. V. Mezhenkova V. M. Karpov V. E. Platonov 《Russian Journal of Organic Chemistry》2011,47(7):1018-1025
The reaction of perfluoro(1-methyl-1-phenyl-1,2-dihydrocyclobutabenzene) with SbF5 at 50°C, followed by hydrolysis, gave perfluoro(1-phenylindan-1-ol), while analogous reaction at 90°C afforded perfluoro[10-methylanthracen-9(10H)-one]. Perfluoro(1-methyl-2-phenyl-1,2-dihydrocyclobutabenzene) did not undergo skeletal transformations under analogous
conditions, whereas at 200°C it was converted mainly into perfluoro(9-methylfluoren-9-ol). Perfluoro(1-ethyl-2-phenyl-1,2-dihydrocyclobutabenzene)
reacted with SbF5 at 200°C to form perfluoro(9-ethylfluoren-9-ol) together with perfluorinated 9,9-dimethyl- and 9-ethyl-9-methyl-1,2,3,4-tetrahydro-9H-fluorenes. 相似文献
2.
Ya. V. Zonov V. M. Karpov V. E. Platonov 《Russian Journal of Organic Chemistry》2010,46(10):1517-1526
Perfluorinated 2-methyl- and 2-ethylbenzocyclobutenones on heating in SbF5 underwent isomerization into perfluoroindan-1-one and perfluoro(2-methylindan-1-one), while their reaction with SiO2—SbF5 gave perfluorinated 3-methyl- and 3-ethylphthalides, respectively. Perfluorinated 2-ethyl-2-methyl- and 2,2-diethylbenzocyclobutenones
reacted with SbF5 to produce perfluorinated 2-(but-2-en-2-yl)- and 2-(pent-2-en-3-yl)-benzoic acids, and their transformations in SbF5 over SiO2 afforded 5,6,7,8-tetrafluoro-1-oxo-3-trifluoromethyl-1H-isochromene-4-carboxylic acid and perfluoro(4-ethyl-3-methyl-1H-isochromen-1-one), respectively. 相似文献
3.
T. V. Mezhenkova V. R. Sinyakov V. M. Karpov V. E. Platonov 《Russian Journal of Organic Chemistry》2012,48(4):529-535
The reaction of perfluoro(1-phenyl-1,2-diethyl-1,2-dihydrocuclobutabenzene) with SbF5 at 20°C, followed by treatment of the
reaction mixture with water gave perfluoro {4-[1-(2-propylphenyl)propylidene]-2,5-cyclohexadien-1-one} together with perfluoro[4b,10-diethylbenzo[a]azulen-7(4bH)-one] resulting from unusual expansion of the pentafluorobenzene ring to seven-membered ring. Analogous reaction at 90°C,
apart from the above compounds, afforded perfluorinated 10-ethyl- and 3,10-diethylbenzo[a]azulen-6(10H)-ones via elimination of C2F5 group from the seven-membered ring or its migration to the benzene ring. 相似文献
4.
T. V. Mezhenkova V. R. Sinyakov V. M. Karpov V. E. Platonov 《Russian Journal of Organic Chemistry》2013,49(10):1454-1465
Perfluorinated 1-ethyl-2-methyl- and 1-isopropyl-2-methyl-1,2-dihydrocyclobutabenzenes reacted with pentafluorobenzene in SbF5 to generate perfluoro(1-ethyl-2-methyl-2-phenyl- and perfluoro(1-izopropyl-2-methyl-2-phenyl-1,2-dihydrocyclobutabenzen-1-yl) cations. These cations in SbF5 at 20°C underwent opening of the four-membered ring and its expansion to five-membered. After hydrolysis, perfluorinated 4-[1-(2-propylphenyl)ethylidene]- and 4-[1-(2-isobutylphenyl)ethylidene]-2,5-cyclohexadien-1-ones were obtained together with perfluoro(3-ethyl- and perfluoro(3-isopropyl-2-phenylinden-1-ones). 相似文献
5.
V. R. Sinyakov T. V. Mezhenkova V. M. Karpov V. E. Platonov T. V. Rybalova Yu. V. Gatilov 《Russian Journal of Organic Chemistry》2006,42(1):77-86
The reaction of perfluoro(1-ethyltetrahydronaphthalene) with pentafluorobenzene in SbF5, followed by treatment of the reaction mixture with water, afforded a mixture of 1-hydroxyperfluoro(1-phenyl-4-ethyletetrahydronaphthalene) and perfluoro(5-phenyl-8-ethyl-2,6,7,8-tetrahydronaphthalen-2-one). From perfluoro(1,1-diethylindan), 1-hydroxyperfluoro(1,1-diethyl-3-phenylindan) was obtained. Perfluoro(1-ethylindan) reacted with an equimolar amount of pentafluorobenzene in SbF5 to give (after hydrolysis) 1-hydroxyperfluoro-(3-ethyl-1-phenylindan), 1-hydroxyperfluoro(3-ethyl-1,3-diphenylindan), and perfluoro(1-ethyl-1-phenylindan), while in the reaction with excess pentafluorobenzene, followed by treatment with anhydrous hydrogen fluoride, perfluoro(1-ethyl-3-phenylindan) and perfluoro(1-ethyl-1,3-diphenylindan) were formed. 相似文献
6.
T. V. Rybalova Yu. V. Gatilov V. R. Sinyakov T. V. Mezhenkova V. M. Karpov 《Journal of Structural Chemistry》2008,49(1):125-130
Perfluorinated 8-phenyl-7,8-diethylbicyclo[4.2.0]octa-1,4,6-trien-3-one (3), 2-(4-oxocyclohexa-2,5-dienylidene)-1,1-diethylbenzocyclobutene (4) and 2-(4-oxocyclohexa-2,5-dienylidene)-5-(2-phenyl-cis-1,2-diethylbenzocyclobuten-1-yloxy)-1,1-diethylbenzocyclobutene (5), including the 4-methylencyclohexa-2,5-dienone fragment, were prepared by the reaction of perfluoro-1,1-(1) and-1,2-diethylbenzocyclobutene (2) with pentafluorobenzene in SbF5. Single crystal X-ray diffraction study of compounds 3–5 revealed that the oxygen atom of the C=O group participated in the formation of supramolecular architectures in all three compounds, and C=O…π bonding may be considered as the corresponding synthon (with increased separation in the case of compound 5). C-F…π bonding acts as a second synthon. F…F interactions in crystals 3–5 were classified as stabilizing or enforced. 相似文献
7.
T. V. Mezhenkova V. M. Karpov V. E. Platonov 《Russian Journal of Organic Chemistry》2011,47(7):1026-1034
Reactions of perfluorinated 1-phenyl-, 1-(2-ethylphenyl)-, 1-(4-ethylphenyl)-, 1-methyl-2-phenyl-, and 1-ethyl-2-phenyl-1,2-dihydrocyclobutabenzenes
with iodine in antimony pentafluoride at 130°C, followed by hydroysis of the reaction mixture, resulted in the formation of
perfluorinated 2-methyl-, 2-ethyl-2′-methyl-, 4-ethyl-2′-methyl-, 2-ethyl-, and 2-propylbenzophenones via opening of the four-membered
ring in the initial cyclobutabenzene at the C1–C2 bond. The presence of hydrogen fluoride facilitates the process and promotes profound transformations leading to anthracene
derivatives. 相似文献
8.
V. I. Potkin S. K. Petkevich A. V. Kletskov I. A. Kolesnik T. D. Zvereva N. A. Zhukovskaya G. G. Levkovskaya I. B. Rozentsveig 《Russian Journal of Organic Chemistry》2017,53(2):240-245
Condensation of acetylferrocene with 5-phenyl(4-methylphenyl)-1,2-oxazole-3-carbaldehydes afforded (Е)-3-[5-phenyl(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-ones. Reactions of (Е)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one with semicarbazide, thiosemicarbazide, and hydroxylamine led to the formation of 5-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-3-ferrocenyl-4,5-dihydro-1H-pyrazole- 1-carboxamide, 5-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-3-ferrocenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide, and 5-(4-methylphenyl)-3'-ferrocenyl-4',5'-dihydro-3,5'-bi-1,2-oxazole respectively. Reactions of (Е)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one with guanidine and thiourea result in 4-[5-(4-methyl-phenyl)-1,2-oxazol-3-yl]-6-ferrocenylpyrimidin-2-amine and -2-thione respectively. 相似文献
9.
The reaction of cyclooctatetraene with methyl diazoacetate or diazoacetone in the presence of rhodium binuclear complexes
gives, besides 9-substituted bicyclo[6.1.0]nona-2,4,6-trienes (mixture ofanti- andsyn-isomers, total yields 60–75%), isomeric β-(cyclohepta-2,4,6-trien-1-yl)acrylates or 4-(cyclohepta-2,4,6-trien-1-yl)but-3-en-2-one
in 20–34% yields. In the case of methyl diazoacetate, a mixture ofE- andZ-isomers in a ratio of −3.5∶1 was obtained, while diazoacetone gave onlyE-isomer.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2204–2206, November, 1999. 相似文献
10.
《Tetrahedron letters》1988,29(6):653-654
By complexing with the title host compound, flipping equilibrium of cycloocta-2,4,6-trien-1-one was frozen in one optical conformer as a 2:1 complex, which upon irradiation gave optically active bicyclo [4.2.0] octa-4,7-dien-2-one. Irradiation of a 1:2 complex of cycloocta-2,4-dien-1-one and the same host compound gave an optically active dimer, anti-tricyclo [8.6.0.02,9] hexadeca-7, 11-diene-3, 16-dione. 相似文献
11.
G. V. Bozhenkov V. A. Savosik E. V. Rudyakova Kha Kuok Khan’ A. I. Albanov L. V. Klyba A. N. Mirskova G. G. Levkovskaya 《Russian Journal of Organic Chemistry》2008,44(12):1745-1751
The reaction of chloroacetyl chloride with 1,2-dichloroethene in the presence of AlCl3 unexpectedly led to the formation of (E)-1,1,4-trichlorobut-3-en-2-one whose structure was proved by 1H and 13C NMR, IR, and mass spectra and independent synthesis. A probable reaction scheme was proposed, which involves transformation of initially formed 1,2,4-trichloro-3-oxobutan-2-yl cation by the action of AlCl3. The high reactivity of the vinylic halogen atom in (E)-1,1,4-trichlorobut-3-en-2-one was demonstrated by its reactions with nitrogen-centered nucleophiles (triethylamine, aniline, 3,5-dimethyl-1H-pyrazole) and sodium sulfide. These reactions involved only the C-Cl bond in the vinyl fragment and afforded (4,4-dichloro-3-oxobut-2-en-1-yl)triethylammonium chloride, 1,1-dichloro-4-phenylaminobut-3-en-2-one, 1-(4,4-dichloro-3-oxobut-2-en-1-yl)-3,5-dimethyl-1H-pyrazole, and 4,4′-thiobis(1,1-dichlorobut-3-en-2-one), respectively. The reaction of 1,1,4-trichlorobut-3-en-2-one with benzylhydrazine gave a mixture of 1,3- and 1,5-disubstituted pyrazoles. 相似文献
12.
XinDongGUO ZhiShuHUANG YaDanBAO LinKunAN LinMA LianQuanGU 《中国化学快报》2005,16(1):49-52
A new sesquiterpenoid lactone, 3,6,9-trimethyl-pyrano[2,3,4-de]chromen-2-one (1) and a novel sesquiterpenoid quinone, 6-[2-(5-acetyl-2,7-dimethyl-8-oxo-bicyclo[4.2.0]octa-l,3,5-trien-7-yl)-2-oxo-ethyl]-3,9-dimethylnaphtho[1,8-bc]pyran-7,8-dione (2) together with a known perezone (3) were isolated from the roots of Helicteres angustifolia. The structures were elucidated as mainly on the basis of ID and 2D NMR spectroscopic data. 相似文献
13.
Sal’nikova T. V. Dmitriev M. V. Maslivets A. N. 《Russian Journal of Organic Chemistry》2019,55(3):314-318
Ethyl 4,5-dioxo-2-phenyl-4,5-dihydro-1H-pynole-3-carboxylates reacted with indan-1,3-dione and 3-amino-1-phenylbut-2-en-1-one or 3-aminobut-2-enenitrile to give 3-benzoyl-2-methyl-2′,5-dioxo-5′-prienyl-1,1′,2′,5-tetrahydrospiro[indeno[1,2-b]pyridine-4,3′-pyrroles] and 2-methyl-2′,5-dioxo-5′-phenyl-1,1′,2′,5-tetrahydrospiro[indeno[1,2-b]pyridine-4,3′-pyrrole]-3-carbonitriles, respectively.
相似文献14.
V. O. Topuzyan A. R. Manvelyan V. V. Grigoryan R. A. Tamazyan A. G. Aivazyan 《Russian Journal of Organic Chemistry》2013,49(6):886-889
4-Benzylidene-2-phenyl-1,3-oxazol-5(4H)-one reacts with piperidin-2-ylmethanamine to give N-{(Z)-3-oxo-3-[(piperidin-2-ylmethyl)amino]-1-phenylprop-1-en-2-yl}benzamide, N-(4-benzyl-3-oxooctahydro-2N-pyrido[1,2-a]pyrazin-4-yl)benzamide, or/and (Z)-4-benzylidenehexahydro-2H-pyrido[1,2-a]pyrazin-3(2H)-one, depending on the solvent, temperature, and reaction time. The latter product is formed via three-step tandem process. 相似文献
15.
P. P. Mukovoz V. O. Koz’minykh A. V. Gorbunova E. N. Koz’minykh P. A. Slepukhin I. N. Ganebnykh O. S. El’tsov 《Russian Journal of Organic Chemistry》2016,52(6):838-843
Reactions of 1,6-diphenylhexane-1,3,4,6-tetraone, octane-2,4,5,7-tetra-one, and decane-3,5,6,8-tetraone with a mixture of p-toluidine and benzaldehyde afforded, respectively, 2-[4-benzoyl-3-hydroxy-1-(4-methylphenyl)-5-phenyl-1H-pyrrol-2-yl]-1-phenylethanone, (1E)-1-[4-acetyl-3-hydroxy-1-(4-methylphenyl)-5-phenyl-1,5-dihydro-2H-pyrrol-2-ylidene]propan-2-one, and 2-hydroxy-1-(4-methylphenyl)-2-(2-oxobutyl)-4-propanoyl-5-phenyl-1,2-dihydro-3H-pyrrol-3-one. 相似文献
16.
A. Heshmat Moustafa Samia A. El-Abbady R. Alan Jones 《Journal of heterocyclic chemistry》1981,18(7):1461-1463
Cycloaddition to 1-(4,6-dimethylpyrimidin-2-yl)- and 1-(4,6-dimethoxy-s-triazin-2-yl)-3-oxidopyridinium betaines across the 2,6-positions of the pyridine rings with indene, acenaphthylene and ethyl cinnamate gave substituted 8-aza[3.2.1]bicycIooct-3-en-2-ones, whereas the [6π + 4π] cycloaddition reaction with 6,6-dimethylfulvene gave a tricyclo[6.3.1.02.6]dodeca-2,(6),4,9-trien-11-one. Structural and configurational assignments of the cycloadducts were deduced from 1H nmr and ir spectral data. 相似文献
17.
Ippolito Antonini Francesco Claudi Gloria Cristalli Mario Grifantini Sante Martelli 《Journal of heterocyclic chemistry》1981,18(2):399-404
The course of the thermal decomposition of various 2-amino-3-substituted aziridino-1,4-naphthoquinones (Ia-g) was investigated. In all the cases, the thermal decomposition gave variable amounts of 2,3-diamino-1,4-naphthoquinone (II) and of substituted 1,2,3,4,5,10-hexahydrobenzo[g]quinoxaline-5,10-diones (IIIa-g) with complete stereospecificity. The decomposition of the aziridines Ib,f also gave significative amounts of 2-amino-3-allylamino-1,4-naphthoquinones (IVb,f). In the case of 2-amino-3-(2′-phenyl-3′-ethylaziridino)-1,4-naphthoquinone (Ig), the formation of trans-1-phenyl-1-butene (V), 2-(1-phenylpropyl)-1H-naphtho-imidazole-4,9-dione (VI), 2-phenyl-3-ethyl-3,4,5,10-tetrahydrobenzo[g]quinoxaline-5,10-dione (VII), 2-phenyl-3-ethyl-5,10-dihydrobenzo[g]quinoxaline-5,10-dione (VIII), and a mixture of cis- and trans-4H-2,3,5,6-tetra-hydro-2-phenyl-3-ethyl-5-iminonaphtho[1,2-b]oxazin-6-one (IX) also occurred. Hypotheses concerning the mechanism and the steric course of this reaction are given. The reaction is a general method for the stereospecific synthesis of 2,3-disubstituted 1,2,3,4,5,10-hexahydrobenzo[g]quinoxalines. 相似文献
18.
Chiang Y Gaplovsky M Kresge AJ Leung KH Ley C Mac M Persy G Phillips DL Popik VV Rödig C Wirz J Zhu Y 《Journal of the American Chemical Society》2003,125(42):12872-12880
Light-induced deazotization of 3-diazo-3H-benzofuran-2-one (1) in solution is accompanied by facile (CO)-O bond cleavage yielding 6-(oxoethenylidene)-2,4-cyclohexadien-1-one (3), which appears with a rise time of 28 ps. The expected Wolff-rearrangement product, 7-oxabicyclo[4.2.0]octa-1,3,5-trien-8-ylidenemethanone (4), is not formed. The efficient light-induced formation of the quinonoid cumulenone 3 opens the way to determine the reactivity of a cumulenone in solution. The reaction kinetics of 3 were monitored by nanosecond flash photolysis with optical (lambda(max) approximately 460 nm) as well as Raman (1526 cm(-1)) and IR detection (2050 cm(-)(1)). Remarkably, the reactivity of 3 is that expected from its valence isomer, the cyclic carbene 3H-benzofuran-2-one-3-ylidene, 2. In aqueous solution, acid-catalyzed addition of water forms the lactone 3-hydroxy-3H-benzofuran-2-one (5). The reaction is initiated by protonation of the cumulenone on its beta-carbon atom. In hexane, cumulenone 3 dimerizes to isoxindigo ((E)-[3,3']bibenzofuranylidene-2,2'-dione, 7), coumestan (6H-benzofuro[3,2-c][1]benzopyran-6-one, 8), and a small amount of dibenzonaphthyrone ([1]benzopyrano[4,3-][1]benzopyran-5,11-dione, 9) at a nearly diffusion-controlled rate. Ab initio calculations (G3) are consistent with the observed data. Carbene 2 is predicted to have a singlet ground state, which undergoes very facile, strongly exothermic (irreversible) ring opening to the cumulenone 3. The calculated barrier to formation of 4 (Wolff-rearrangement) is prohibitive. DFT calculations indicate that protonation of 3 on the beta-carbon is accompanied by cyclization to the protonated carbene 2H(+), and that dimerization of 3 to 7 and 9 takes place in a single step with negligible activation energy. 相似文献
19.
G. S. Borodkin A. A. Kolodina E. A. Gusakov I. G. Borodkina P. B. Chepurnoi S. B. Zaichenko Yu. A. Sayapin V. I. Minkin 《Russian Journal of Organic Chemistry》2016,52(7):1007-1011
The reaction of 2-methylquinoline with 3,5-di-tert-butyl-1,2-benzoquinone afforded a mixture of 5,7-di-tert-butyl-3-hydroxy-2-(quinolin-2-yl)cyclohepta-2,4,6-trien-1-one and previously unknown 10-tert-butylindolo[1,2-a]quinoline-8,11-dione. The structure of the latter was determined by two-dimensional heteronuclear correlation NMR spectroscopy. 相似文献
20.
Utility and limitation of the title reaction was studied. When (E)-3-(4-t-butyl- and 4-phenylcyclohex-1-en-1-yl)-2-(trimethylsilylmethyl)prop-2-en-1-ols were treated with Ms2O or MsCl, 3-t-butyl- and 3-phenyl-8-methylbicyclo[4.3.0]nona-1(6),7-dienes were obtained, respectively. The corresponding (Z)-isomer afforded a complex mixture, among which an elimination product was detected. (E)-4-(4-t-Butylcyclohexylidene)-2-(trimethylsilylmethyl)but-2-en-1-ol afforded only elimination product. 相似文献