54939-04-7Relevant academic research and scientific papers
Photosensitized defluorination of saturated perfluorocarbons
Kaprinidis, Nikolas A.,Turro, Nicholas J.
, p. 2373 - 2376 (1996)
UV irradiation of perfluorodecalin 1 in the presence of an electron donor results in the facile formation of perfluoroolefin 2 from the selective elimination of the vicinal tertiary fluorines.
Functionalization of saturated fluorocarbons
Stoyanov, Nikolay S.,Ramchandani, Nita,Lemal, David M.
, p. 6549 - 6552 (2007/10/03)
A method is described for transforming perfluoroalkanes and perfluorocycloalkanes bearing tertiary fluorine into perfluoroenolates, which can be variously derivatized.
Interaction of perfluorocarbons with carbon
Weigert, F. J.
, p. 67 - 72 (2007/10/02)
Activated carbon is an effective stoichiometric fluorine acceptor which defluorinates perfluoroalkanes with the partial structure (Rf)2CFCF(Rf)2 to alkenes and perfluoroalkenes to dienes.Carbon catalyzes double-bond shifts, as well as cis/trans and ring-chain perfluoro-olefin isomerizations.Carbon effectively catalyzes TFE and HFP dimerizations.Less effecively, carbon catalyzes further oligomerization of TFE to give low yields of linear, internal olefins.Free radicals may be the key surface intermediates.
POLYFLUOROBICYCLO 4,4,0 DECANES. PART II. THE FLUORINATION OF TETRALIN BY POTASSIUM TETRAFLUOROCOBALTATE(III)
Coe, Paul L.,Hu, Chang-Ming,Tatlow, John Colin
, p. 35 - 44 (2007/10/02)
Fluorination of tetralin, using potassium tetrafluorocobaltate(III) at 275-300 deg C, gave a series of compounds with bicyclodecane skeletons, as follows: -hexadecafluoro-1(6)-ene (1); tetradecafluoro-1(6),3(4)-diene (2); 3H-pentadecafluoro-1(6)-ene (3); perfluorotetraline (6) (all reported earlier); 8H-tridecafluoro-1(6),3(4)-diene (4); 3H,4H-tetradecafluoro-1(6)-ene (5); a mixture of 3H,8H- and 3H,9H-tetradecafluoro-1(6)-ene (7 and 8); 2H-undecafluorotetralin (9); 3H,4H,8H-tridecafluoro-1(6)-ene (10).The structures of all the new products (4,5,7-10) were determined by elemental analysis, protone and fluorine nmr, and mass spectrometry.Obviously, with this reagent, the residual 1(6) double bond and the β-hydrogens are the most difficult to replace.
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.
FLUORINATION OF POLYFLUOROAROMATIC COMPOUNDS WITH VANADIUM PENTAFLUORIDE
Bardin, V. V.,Avramenko, A. A.,Furin, G. G.,Yakobson, G. G.,Krasilnikov, V. A.,et al.
, p. 37 - 46 (2007/10/02)
Fluorination of polyfluoro-derivatives of benzene and diphenyl with vanadium pentafluoride at -25 to -10 deg C afforded fluorinated cyclohexadienes and cyclohexenes.Octafluoronaphthalene was converted under these conditions to perfluoro-1,4-dihydronaphthalene, perfluorotetralin, perfluoro-1,4,5,8-tetrahydronaphthalene and perfluoro-1,2,3,4,5,8-hexahydronaphthalene.
AROMATIC FLUORINE DERIVATIVES. XCVII. OXIDATIVE FLUORINATION OF PERFLUORINATED AROMATIC COMPOUNDS WITH VANADIUM PENTAFLUORIDE
Bardin, V. V.,Furin, G. G.,Avramenko, A. A.,Krasil'nikov, V. A.,Tushin, P. P.,et all
, p. 307 - 311 (2007/10/02)
Perfluorinated aromatic compounds are converted by the action of vanadium pentafluoride at -25 to -15 deg C into perfluorinated derivatives of cyclohexadiene and cyclohexene.The rate of addition of the two fluorine atoms to the perfluorinated derivatives of 1,3- and 1,4-cyclohexadiene under conditions of competing fluorination depends on the nature of the substituent at the carbon-carbon double bond.
