112754-18-4Relevant academic research and scientific papers
Opening of the four-membered ring in perfluorinated 1-alkyl-2-phenyl-and 1-aryl-1,2-dihydrocyclobutabenzenes in the system I2-SbF5
Mezhenkova,Karpov,Platonov
experimental part, p. 1026 - 1034 (2011/10/19)
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.
Cationoid rearrangements in reactions of perfluoro-1-arylbenzocyclobutenes with antimony pentafluoride
Karpov, Victor M.,Mezhenkova, Tatyana V.,Platonov, Vyacheslav E.,Sinyakov, Vladimir R.
, p. 73 - 81 (2007/10/03)
In the presence of antimony pentafluoride at 130°C, the four-membered ring of perfluoro-1-(2-ethylphenyl)benzocyclobutene (2) undergoes cleavage, forming perfluoro-2-ethyl-2′-methyldiphenylmethane (5). Compound 5 is converted, under the action of SbF5 at 170°C, to perfluoro-8,9-dimethyl-1,2,3,4-tetrahydrofluorene (8). Perfluoro-1-(4-ethylphenyl)benzocyclobutene (3) remains unchanged at 130°C, whereas at 170°C it gives a mixture of perfluorinated 4′-ethyl-2-methyldiphenylmethane (9), 6-ethyl-1,2,3,4-tetrahydroanthracene (11) and 2-ethyl-9,10-dihydroanthracene (12). When heated with SbF5 at 170°C, perfluoro-1-phenylbenzocyclobutene (1) remains unchanged. Solution of compounds 2, 3, 5 and 9 in SbF5-SO2ClF generated the perfluorinated 1-(2-ethylphenyl)-1-benzocyclobutenyl (29), 1-(4-ethylphenyl)-1-benzocyclobutenyl (30), 2-ethyl-2′-methyldiphenylmethyl (31) and 4′-ethyl-2-methyldiphenylmethyl (32) cations, respectively.
Fluorination and skeletal transformations of perfluorobenzocycloalkenes in reactions with antimony pentefluoride
Karpov, Victor M.,Mezhenkova, Tatyana V.,Platonov, Vyacheslav E.,Yakobson, Georg G.
, p. 980 - 985 (2007/10/02)
The reactions of perfluorobenzocycloalkenes containing the four-, five- and six-membered cycles with antimony pentafluoride, in the presence of bromine or its absence, have been studied.The alicyclic ring cleavage of benzocycloalkenes, unknown in the fluorinated series, has been found.Perfluorobenzocyclobutene in the presence of SbF5 gave perfluoro-2-(1-benzocyclobutenyl)ethylbenzene; but in the system SbF5 - Br2 bromoperfluoro-2-ethylbenzene was obtained.Heating perfluoro-indan, -4-methyl- and -5-methylindanes with antimony pentafluoride led to their transformation into perfluoroalkylbenzenes with the ethyl group situated in the ortho-position to the methyl group.Similarly perfluoro-1-methylindan and perfluorotetralin were converted to perfluoro-2-isopropyltoluene.By contrast with this, perfluoro-2-methylindan was fluorinated by SbF5 to perfluoro-2-methyl-4,5,6,7-tetrahydroindan.Perfluoro-indan, -4-methyl- and -5-methylindanes were fluorinated by SbF5 in the presence of bromine.Under these conditions, perfluorotetralin gave perfluorooctalin and perfluoroindan was transformed into perfluoro-4,5,6,7-tetrahydroindan.The latter product was also quite unexpectedly formed from perfluoro-4-methyl- and -5-methylindanes.
