- Photolysis of Perfluoroazooctane in Perfluorohexane upon 185 nm Irradiation
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The photolysis of perfluoroazooctane in perfluorohexane upon 185 nm irradiation was investigated by means of quantum yield, light intensity dependence, and UV-vis spectra of the photolysis of perfluoroazooctane.Perfluoroazooctane (trans isomer) was photoi
- Nakamura, Takako,Yabe, Akira
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- Perfluorooctylation of aromatic compounds with perfluoroazooctane upon 185 nm irradiation in a two-phase system
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An efficient method for the preparation of perfluorooctylated aromatic and heteroaromatic compounds has been developed using photolysis of perfluoroazooctane (E)-1 upon 185 nm irradiation. The use of a two-phase system made up of a perfluorohexane solution of (E)-1 and a suitable aromatic compound has proved efficient for this reaction. The photolytic mechanism of (E)-1 upon 185 nm irradiation has also been investigated on the basis of quantum yield, light intensity dependence and UV-VIS spectra. It is shown that (E)-1 is photoisomerized by one photon absorption to the (Z)-isomer, with subsequent extrusion of nitrogen by a second photon absorption.
- Nakamura, Takako,Koga, Yoshinori
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- A Direct Introduction of Perfluorooctyl Group into Cycloalkanes using the Photolysis of Perfluoroazooctane upon 185 nm Irradiation
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Perfluorooctyl-substituted cycloalkanes are prepared directly by photolysis of perfluoroazooctane in cycloalkanes upon 185 nm irradiation; a plausible mechanism is discussed on the basis of the time-course, quantum yield, and light intensity dependence during this photoreaction.
- Nakamura, Takako,Yabe, Akira
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- METHOD FOR PRODUCING TETRAFLUOROETHYLENE AND/OR HEXAFLUOROPROPYLENE
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PROBLEM TO BE SOLVED: To provide a novel method for producing tetrafluoroethylene and/or hexafluoropropylene. SOLUTION: The method for producing tetrafluoroethylene and/or hexafluoropropylene comprises thermally decomposing a perfluoroalkane represented by the general formula (1) defined by CnF2n+2, where n represents an integer of 4-28.] COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0051
(2016/11/09)
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- An improved procedure for the synthesis of perfluoroalkylacetylenes
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A new and easy way to synthesize acetylene compounds is proposed. This synthesis is improved by including in one-pot, three reactions in a single step, with good yields. The reactants are commonly used compounds.
- Calleja-Rubio,Crette,Blancou
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p. 361 - 364
(2007/10/03)
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A new synthesis of perfluoroalkylmethyloxiranes and perfluoroalkylmethylaziridines is accomplished by addition of allylalcohol or allylamine to iodoperfluoroalkanes in the presence of potassium or sodium hydroxide.
- Rubio,Blancou,Commeyras
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- Reaction of Perfluoroalkyl Iodides with Lithium Salt of 5-Nitro-3-tert-butyl-1,3-tetrahydrooxazine
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Reaction of perfluoroalkyl iodides C6F13I and C8H17I with lithium salt of 5-nitro-3-tert-butyl-1,3-tetrahydrooxazine in DMSO at 20°C for 24 h in an argon atmosphere gives 5-nitro-5-perfluoroalkyl-3-tert-butyl-1,3-tetrahydrooxazines (yield 66-75%), 5,5′-bis(5-nitro-3-tert-butyltetrahydro-1,3-oxazinyl) (yield 3-5%), and, respectively, perfluorododecane and perfluorohexadecane. The reaction is accelerated under UV irradiation.
- Galeeva,Makaeva,Zorin,Trifonova,Rakhmankulov
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p. 280 - 282
(2007/10/03)
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- Electroorganic synthesis 65. Anodic homocoupling of carboxylic acids derived from fatty acids
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Fatty acid derived carboxylic acids with double bonds, hydroxy-, amino-, keto-, ester- and epoxy groups are anodically coupled to dimers (Kolbe electrolysis) in 29 to 81% yield and up to a 2.5 mol scale. Problems due to the low conductivity of fatty acid salts were overcome by the use of a flow cell with a narrow electrode gap. Fatty acids with branched alkyl chains gave dimers with interesting emulsifying properties. Dimethyl hexadecanedioate, accessible from methyl azelate, could be cyclized and further converted into homomuscone and muscone in a few steps. A commercial mixture of dimeric fatty acids (C36-dicarboxylic acids) has been coupled to give C70-diesters. Acta Chemica Scandinavica 1998. Part 64: Nielsen, M. F., Batanero, B.,.
- Weiper-Idelmann, Andreas,Aus Dem Kahmen, Martin,Schaefer, Hans J.,Gockeln, Marianne
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p. 672 - 682
(2007/10/03)
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- Perfluoroalkylation of Benzene by 185 nm Photolysis of Perfluoroazooctane
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Perfluoroazooctane was photolyzed in benzene upon low pressure Hg lamp irradiation to generate perfluorooctyl radicals, which reacted with an excess of benzene to afford perfluorooctylbenzene.The investigation on the wavelength and light intensity dependence revealed that this photolysis proceeded effectively upon 185 nm irradiation by two photon absorption.
- Nakamura, Takako,Yabe, Akira
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p. 1573 - 1576
(2007/10/02)
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- Solvent effects on the reaction of perfluoroalkyl iododes and α,ω-perfluoroalkyl diiodides with cadmium powder and dimethylcadmium
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Reaction of RfI (Rf=C6F13 or C8F17) with Cd powder in DMF at room temperature under N2 afforded RfCdX (X=I or Rf) in moderate (48-52percent) yield.Although no reaction was observed with Cd powder and RfI (Rf=C6F13 or C8F17) in CH3CN at room temperature, reaction at reflux gave the homocoupled products C6F13-C6F13 (67percent) and C8F17-C8F17 (61percent) respectively.No F-alkylcadmium reagent was detected by 19F NMR spectroscopy.Similarly, the reaction of I(CF2)nI (n=3, 4) with Cd powder in DMF and CH3CN was examined.In DMF at room temperature, the new dicadmium reagents ICd(CF2)nCdI and ICd(CF2)2nCdI (60-65percent combined yield) were formed.No reaction was observed with Cd powder and I(CF2)nI (n=3, 4, 6) in CH3CN at room temperature, but at reflux a mixture of higher α,ω-diiodoperfluoroalkanes, i.e.I(CF2)2nI, I(CF2)3nI, I(CF2)4nI, I(CF2)5nI, resulted.Treatment of I(CF2)nI (n=3, 4) with CdMe2 (1:2) in CH3CN afforded the new ω-iodo F-alkylcadmium reagents, 2Cd*(CH3CN), in 96percent (n=3) and 57percent (n=4) yields.Reaction of Me2Cd with either ICF2CF2I or BrCF2CF2I in CH3CN or HMPA at 0 deg C resulted in tetrafluoroethylene only.
- Nair, Haridasan K.,Burton, Donald J.
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- SYNTHESIS OF PERFLUOROALKYL CARBOXYLIC ACIDS BY REACTION OF PERFLUOROALKYL IODIDES WITH ELECTROGENERATED SUPEROXIDE ION
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The electrogenerated superoxide ion O2 is shown to react with perfluoroalkyliodides to afford F-alkyl carboxylic acids.A mechanism is proposed on the basis of the results obtained in preparative experiments and by cyclic voltammetry.
- Amatore, C.
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p. 357 - 379
(2007/10/02)
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- SOLVENT EFFECTS IN BETWEEN PERFLUOROALKYLIODIDES AND CADMIUM
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The interaction between perfluoroorgano iodides (RfI where Rf = F(CF3)2C(CF2CF2)3, n-C6F13, n-C8F17, F(CF3)2COCF2CF2, F(CF3)2CO(CF2CF2)4 and C2H5OC(O)(CF2CF2)2OCF2CF2) with cadmium in an acetonitrile solvent media produces primarily the coupled products (RfRf, 72-90percent yield) in addition to minor quantities of the reduction products (RfH).On the other hand ICF2CF2I and ClCF2CFClI, by a 1,2-dehalogenation reaction, from the olefins CF2=CF2 and CF2=CFCl, respectively, as the principal products.The interaction of RfI compounds with cadmium in other solvent media, e.g. diethyl ether, tetrahydrofuran (YHF)), N,N-dimethylformamide (DMF), and bis(2-methoxyethyl)ether(diglyme) were examined and found to produce a different ratio of RfRf and RfH products.
- Chen, Grace J.,Tamborski, Christ
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p. 123 - 140
(2007/10/02)
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- THERMAL DECOMPOSITION OF PERFLUOROALKANESULFONYL FLUORIDES: THE PYROLYSIS OF PERFLUORO-n-OCTANE-1-SULFONYL FLUORIDE
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The preliminary data obtained from thermal decompositions of perfluoro-n-octane-1-sulfonyl fluoride in a continuous tubular-flow reactor are reported.The pyrolysis results in a radical reaction producing fluorocarbons, with high conversions and with yields depending on the experimental conditions.The reaction mixture composition also depends on the experimental conditions, so it is possible to obtain a prevalent formation of either light or heavy fluorocarbons.
- Napoli, M.,Fraccaro, C.,Scipioni, A.,Armelli, R.
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p. 377 - 386
(2007/10/02)
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- REACTIVITE DES PERFLUOROIODOALCANES AVEC LES CARBONATES ET PYROCARBONATES D'ALCOYLES EN PRESENCE DE COUPLE METALLIQUE ZINC-CUIVRE
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Perpluoroalkyl iodides RFI, in dissociating solvents, in the presence of zinc-copper couple give perfluoroorganic compounds RFZnI, which reac with alkyl carbonates and pyrocarbonates to give perfluorocarboxylic acids and perfluorocarboxylis esters of industrial interest.
- Benefice, S.,Blancou, H.,Commeyras, A.
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p. 1541 - 1544
(2007/10/02)
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- DIRECT PERFLUOROALKYLATION OF FUNCTIONALIZED BENZENES WITH PERFLUOROALKYL HALIDES AND COPPER BRONZE
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Perfluoroalkyl halides were found to react with functionalized benzenes in the presence of copper bronze to give the corresponding perfluoroalkylated products directly in moderate to good yields.The reaction may involve' active species' other than perfluoroalkylcopper species.Synthetic utility and possible mechanisms of the present one-step reaction are discussed.
- Fuchikami, Takamasa,Ojima, Iwao
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p. 541 - 556
(2007/10/02)
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- UTRASOUND-PROMOTED DIRECT CARBOXYLATION OF PERFLUOROALKYL IODIDES
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Perfluoroalkyl iodides were directly carboxylated with Zn and CO2 under utrasonic irradiation affording the corresponding perfluoroalkanoic acids.
- Ishikawa, Nobuo,Takahashi, Mitsuru,Sato, Takehiko,Kitazume, Tomoya
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p. 585 - 588
(2007/10/02)
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