- REACTION OF 2-TRIFLUOROMETHYLPERFLUORO-2-PENTENYL FLUOROSULFATE WITH NUCLEOPHILIC REAGENTS
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2-Trifluoromethylperfluoro-2-pentenyl fluorosulfate undergoes SN2' nucleophilic reactions.The reaction of this fluorosulfate with halide salts gives an equilibrium mixture of 1-halo-2-trifluoromethylperfluoro-2-pentene and 2-trifluoromethyl-3-haloperfluoro-1-pentene.
- Avetisyan, E. A.,Cherstkov, V. F.,Snegirev, V. F.,Sterlin, S. R.,German, L. S.
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- ADDITION OF tert-PERFLUOROALKYL BROMIDES AT A MULTIPLE BOND, INITIATED BY ELECTRON TRANSFER
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The thermodynamics of the dissociation of the radical-anions of perfluoroalkyl halides was determined by quantum-chemical methods.The conditions for the addition of tertiary perfluoroalkyl bromides to alkenes, initiated by electron transfer, were obtained.
- Igumnov, S. M.,Rozhkov, I. N.,Pletnev, S. I.,Borisov, Yu. A.,Rempel', G. D.
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- Functionalization of saturated fluorocarbons
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A method is described for transforming perfluoroalkanes and perfluorocycloalkanes bearing tertiary fluorine into perfluoroenolates, which can be variously derivatized.
- Stoyanov, Nikolay S.,Ramchandani, Nita,Lemal, David M.
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- Novel Fluorine-Bridged Polyfluorinated Iodine Structures. Presence of Fluorine as the Central Atom in a Five-Center Six-Electron Bond
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The reaction of tris(dialkylamino)sulfonium perfluoro-2-methyl-2-pentyl carbanion with perfluoro iodides (RfI) leads to novel structures of the form f-I-F-I-Rf>-.The crystal structure for RfI = pentafluorophenyl iodide reveals discrete ion pairs.The crystal structure for RfI = 1,4-diiodooctafluorobutane shows an extended polymeric structure with (CF2)4 groups bridged by - units.The I-F bond distances are 0.3 - 0.4 Angstroem longer than normal fluorine-iodine distances but are > 1.0 Angstroem shorter than the sum of the van der Waals radii.The Rf-I-F bond angles are quasi-linear wheras the I-F-I bond angles deviate from linearity by 10 degree - 20 degree.High-level ab initio calculations of c-I-F>- and c-I-CF3>- are presented.The free ions are calculated to have linear structures at I and at the central fluorine.The Rf-I bond distances are calculated to be slightly longer than those in a free Rf-I compound, and the I-Fc bond distances are significantly elongated as compared to free I-F.The vibrational analysis shows a very low bending frequency of 28 cm-1 at the central fluorine in -.Analysis of the wave functions shows that the bonding in these structures is best described by a five-center, six-electron (5c 6e) hypervalent ? bond and not as an ion-dipole complex.The 5c 6e bond is stabilized by more electronegative elements at the central and terminal positions and less electronegative elements at the other two positions.The negative charge is found at the central and terminal positions.The alkyl fluorides stabilize the excess negative charge at the terminal position by negative anionic hyperconjugation.
- Farnham, William B.,Dixon, David A.,Calabrese, Joseph C.
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- OLIGOMERIZATION OF PERFLUOROPROPYLENE CATALYZED BY ?-BIS(ARENE)CHROMIUM(0) COMPLEXES
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Oligomerization of perfluoropropylene catalyzed by four ?-bis(arene)chromium(0) complexes (arene = benzene, diphenyl, 1,3,5-trimethylbenzene and hexamethylbenzene) were compared.Besides dimers (I, II) and trimers (III, IV) reported previously , two defluorotrimers VA and VB were found to be present in the oligomer mixtures.The formation of VA and VB was shown to be derived from trimer IV by hydrogenation followed by elimination of two moles of hydrogen fluoride.
- Huang, Yaozeng,Li, Jisen,Zhou, Jianqiang,Wang, Qiwen,Gui, Meimei
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- On reactions of carbon disulphide induced by 'naked' fluoride part 2: Reactions with 2-H-heptafluoropropane, hexafluoropropene, and bis (2,2,2-trifluoroethyl) amine
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The reaction of CS2 and tetramethylammonium fluoride (TMAF) with 2-H-heptafluoropropane (R227) leads to 2,4-bis(hexafluoroisopropylidene)-1,3-dithietane as well as to the tetramethylammonium salt of heptafluorodithioisobutyric acid. The latter anion resulted also from the reaction of CS2 and CsF with hexafluoropropene (HFP), whereas CS2, TMAF and HFP reacted to compounds derived from HFP dimerization. N,N-bis (2,2,2-trifluoroethyl) dithiocarbamic acid anion was obtained from bis (trifluoroethyl) amine reacted with CS2 and TMAF.
- Ruediger, Stephan,Seppelt, Konrad
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- Reactions Involving Fluoride Ion. Part 40. Amines as Initiators of Fluoride Ion Catalysed Reactions
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Tetrakis(dimethylamino)ethene (TDAE) and trimethylamine react with anhydrous unsaturated fluorocarbons to produce, 'in situ', powerful fluoride-ion sources.These are used to iniate carbon-carbon bond forming reactions eg. oligomerisation and polyfluoroalkylation, and many of these reactions occur efficiently in the absence of a solvent.
- Chambers, Richard D.,Gray, William K.,Korn, Stewart R.
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- Synthesis of (2E)-2-(tetrafluoroethylidene)-3,3-bis(trifluoromethyl)-2,3-dihydrothiazolo[3,2- a]benzimidazole
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The reaction of benzimidazoline-2-thione with perfluoro-2-methylpent-2-ene in the presence of triethylamine afforded (2E)-2-(tetrafluoroethylidene)-3,3-bis(trifluoromethyl)-2,3-dihydrothiazolo[3,2- a]benzimidazole whose structure was confirmed by X-ray diffraction analysis. The reaction pathways are discussed.
- Rogoza,Furin,Bagryanskaya,Gatilov
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- REACTIONS OF TERTIARY PERFLUOROALKYL HALIDES WITH HALIDE ANIONS
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The reactivities of the F-tert.-alkyl halides (CF3CF2CF2(CF3)2CX (1a-c: X = I, Br Cl)) towards the corresponding lithium halides LiY (2a-c: Y = I, Br, Cl), in acetonitrile, reflect the electron acceptor properties of compounds 1 and the donator strength of the anions Y(1-).The tertiary carbanion F-2-methylpentanide acts as the key intermediate in the formation of the main products (F-2-methyl-2-pentene, F-2-methyl-1-pentene and F-2-hydro-2-methylpentane), and also of the halide substitution products obtained from 1a.No support for the participation of any perfluoroalkyl radical could be found.
- Blume, Elisabeth,Gasafi-Martin, Waltraud,Probst, Anton,Werner, Konrad von
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- Synthesis method of heptafluoroisobutyronitrile
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The invention provides a synthesis method of heptafluoroisobutyronitrile. The synthesis method comprises the following steps of: A) carrying out ozone cracking on a hexafluoropropylene dimer in the presence of a fluorocarbon solvent and alcohol to prepare heptafluoroisobutyrate; and B) carrying out a reaction between the obtained heptafluoroisobutyrate with ammonia, and dehydrating to obtain heptafluoroisobutyronitrile. DHFP dimer ozone cracking reaction conditions are mild, the raw material conversion rate and the product yield are high, and the whole production process is safe, simple, convenient and reliable in technological operation and easy for industrial production.
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Paragraph 0084-0085
(2020/11/09)
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- Preparation method of perfluoro-2-methyl-2-pentene
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The invention discloses a preparation method of perfluoro-2-methyl-2-pentene. According to the preparation method disclosed by the invention, hexafluoropropylene reacts in a solvent in the presence ofa catalyst and an alkaline substance, so as to obtain the perfluoro-2-methyl-2-pentene; the mass ratio of the hexafluoropropylene to the catalyst is (20 to 100) to 1, the mass ratio of the hexafluoropropylene to the solvent is (1 to 15) to 1, and the mass ratio of the hexafluoropropylene to the alkaline substance is (10 to 100) to 1; the reaction temperature is 40 to 150 DEG C and the reaction time is 3 to 12h. The preparation method of the perfluoro-2-methyl-2-pentene, disclosed by the invention, has the advantages of environment protection, low cost, simple technology, high reaction selectivity and the like.
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Paragraph 0031-0060
(2018/09/08)
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- Synthesis method and application of perfluoro(2-methyl-3-pentanone)
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The invention relates to a synthesis method and application of perfluoro(2-methyl-3-pentanone), and belongs to the technical field of organic synthesis. The synthesis method comprises the following steps: mixing perfluoro(4-methylpent-2-ene) with a solvent; cooling to 13-17 DEG C; adding an oxidant; collecting a reaction product with the largest specific gravity to obtain a perfluoroepoxide; isomerizing the perfluoroepoxide in the presence of the solvent and an amine catalyst; collecting a reaction product with the largest specific gravity; and rectifying and collecting rectification products having a boiling point of 48 to 50 DEG C to obtain the perfluoro(2-methyl-3-pentanone), wherein the solvent comprises acetonitrile and/or dimethylformamide. The synthesis method has the advantages of simple process and relatively high product purity and synthesis yield; the synthesized perfluoro(2-methyl-3-pentanone) can be used as a fire extinguishing agent for fire extinguishing, and is good in fire extinguishing effect, green and environmentally friendly.
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Paragraph 0039; 0043-0044; 0053-0054
(2018/03/01)
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- Perfluoro-2-methyl-2-pentene preparation method
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The invention provides a preparation method for perfluoro-2-methyl-2-pentene. The method comprises the steps that under the existence of catalysts, a polar aprotic solvent is used as a medium, and under the pressure ranging from minus 0.1 MPa to 1.5 MPa, hexafluoropropylene reacts at the first-segment reaction temperature ranging from minus 30 DEG C to 20 DEG C for 1 hour to 6 hours, and then reacts at the second-segment reaction temperature ranging from 20 DEG C to 90 DEG C for 1 hour to 6 hours to obtain perfluoro-2-methyl-2-pentene, wherein the catalysts include the major catalyst and the cocatalyst, the major catalyst is a metal fluoride salt, and the cocatalyst is a guanidine compound.
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Paragraph 0011; 0045; 0046
(2017/03/14)
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- PROCESS FOR THE PREPARATION OF 5-FLUORO-1H-PYRAZOLES STARTING FROM HEXAFLUOROPROPENE
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A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) as described herein and further reactions with this compound.
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Paragraph 0192
(2016/03/18)
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- Method for preparing perfluoro ethyl isopropylacetone
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The invention provides a preparation method of perfluorethyl isopropyl ketone. The preparation method specifically comprises the step of: with a hexafluoropropylene dipolymer mixture and perfluo-4-methyl-2-amylene or perfluo-2-methyl-2-amylene as raw materials, carrying out reaction processes such as olefin epoxidation, structural rearrangement of epoxide to prepare the perfluorethyl isopropyl ketone. An aprotic polar solvent, a catalyst and a phase transfer catalyst are used in a preparation process, high selectivity and high transformation rate of all steps of reactions are realized, and after a reaction mixture is simply separated so that an intermediate and a perfluorethyl isopropyl ketone product with high quality can be obtained. Meanwhile, a one-pot technology of double bond isomerization and epoxidation reaction is established. The preparation method provided by the invention has the characteristics that raw materials are easily available, the cost is low, reaction conditions are mild, operation is safe and simple, reaction selectivity and transformation rate are high, little environment influence is low; therefore, the preparation method is suitable for industrial application.
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Paragraph 0019-0023
(2017/01/19)
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- PROCESS FOR THE PREPARATION OF 5-FLUORO-1H-PYRAZOLES STARTING FROM HEXAFLUOROPROPENE
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A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I)as described herein and further reactions with this compound.
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Paragraph 0207
(2016/01/29)
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- PREPARATION METHOD FOR PERFLUORO-2-METHYL-3-PENTANONE AND INTERMEDIATE
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Disclosed is a preparation method for perfluoro-2-methyl-3-pentanone. In the presence of fluoride salts and ether compounds, perfluoro-2, 3-epoxide-2-methyl pentane is converted into perfluoro-2-methyl-3-pentanone by a catalytic rearrangement reaction, which has characteristics such as mild action condition, fast reaction rate, high reaction selectivity and high yield. The prepared perfluoro-2-methyl-3-pentanone can be used as detergent, solvent and extinguishant. The perfluoro-2, 3-epoxide-2-methyl pentane is prepared by using perfluoro-2-methyl-2-amylene as raw material to react with sodium hypochlorite, and the perfluoro-2-methyl-2-amylene raw material is prepared through the catalytic isomerization reaction by using perfluoro-4-methyl-2-amylene as raw material.
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Paragraph 0083
(2015/05/05)
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- Process for purifying hexafluoropropene dimers
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Perfluoro-4-methyl-2-pentene containing the undesirable perfluoro-2-methyl-2-pentene may be purified by contacting the mixture with at least a stoichiometric equivalent of an aqueous inorganic base (relative to the perfluoro-2-methyl-2-pentene), in the presence of a polar solvent.
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Page/Page column 6-7
(2008/06/13)
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- Electrophilic reactions of fluorocarbons under the action of aluminum chlorofluoride, a potent Lewis acid
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A new Lewis acid - aluminum chlorofluoride - was demonstrated to be an effective catalyst for the isomerisation of fluoroolefins, polyfluorinated epoxides and cyclopropanes.At ambient temperature this catalyst converts perfluorobutadiene-1,3 into perfluorobutyne-2 and perfluoro(4-methylpentene-2) into perfluoro(2-methylpentene-2) in nearly quantitative yield.At 100 deg C, aluminum chlorofluoride causes the cleavage of perfluorinated tertiary amines. - Keywords: Electrophilic reactions; Fluorocarbons; Aluminum chlorofluoride; Lewis acid; NMR spectroscopy
- Petrov, V. A.,Krespan, C. G.,Smart, B. E.
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p. 138 - 142
(2007/10/03)
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- Reversible intramolecular 1,3-chlorine migration in the triad 'carbon-carbon-sulfur'
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An intramolecular 1,3-chlorine migration in the triad 'carbon-carbon-sulfur' with nucleophilic solvent or catalyst assistance is proposed as a mechanism for the perfluoro-2-methylpent-2-ene-3-sulfenyl chloride 12-chloroperfluoro-2-methylpentane-3-thione 2 tautomerism.The data from radionuclidic investigations were used to elucidate the aforementioned mechanism.The results of MNDO calculations showed that the solvation lowers the height of the reaction barriers of both direct and reverse reactions and brings about different reaction pathways for these two processes, providing greater assistance to the 1->2 than to the 2->1 reaction.
- Popkova, Vera Ya.,Anisimov, Victor M.,Dolenko, Georgii N.,Semenenko, Mikhail N.,Fedoseev, Vladimir M.
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p. 1375 - 1380
(2007/10/02)
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- Reactions involving fluoride ion. Part 37. "Proton Sponge" hydrofluoride as a fluoride ion donor
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"Proton Sponge" hydrofluoride has been prepared and is totally soluble in acetonitrile; this system has been used to generate carbanions from hexafluoropropene and to form carbon-fluorine bonds by reaction with both 2,4,6-trichloropyrimidine and benzoyl chloride.
- Chambers, Richard D.,Korn, Stewart R.,Sandford, Graham
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p. 103 - 108
(2007/10/02)
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- ELECTRON TRANSFER IN REACTIONS OF tert-PERFLUOROALKYL BROMIDES WITH ALKENES AND NUCLEOPHILES
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Tertiary perfluoroalkyl bromides (RFBr) in nonpolar solvents under mild conditions can be added to the multiple bond of terminal alkenes, alkynes, and butadiene.Slow addition to alkenes at 20 deg C is accelerated in proton-donating solvents and is catalyzed by readily oxidizable nucleophiles.Bromination of the multiple bond and formation of RFBr reduction products suggests a radical-chain mechanism initiated by electron transfer to the RFBr molecule.
- Rozhkov, I. N.,Chaplina, I. V.
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p. 2451 - 2456
(2007/10/02)
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- α,β-UNSATURATED FLUORINE-CONTAINING THIOCYANATES
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A new method has been developed for the synthesis of perfluorinated α,β-unsaturated thiocyanates by the reaction of the corresponding sulfenyl chlorides with KCN in water.The thiocyanate form of perfluoro-2-methyl-2-pentene-3-thiocyanate was isomerized to the isothiocyanate form.This rearrangement is initiated by both fluoride and thiocyanate anions.
- Popkova, V. Ya.,Mysov, E. I.,Galakhov, M. V.,Osmanov, V. K.,German, L. S.
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p. 2599 - 2602
(2007/10/02)
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- Standard enthalpies of formation of hexafluoropropene oligomers
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The energies of combustion at 298.15 K of perfluoro-2-methylpent-2-ene and perfluoro-2-methyl-3-isopropylpent-2-ene (-1993.7 +/- 4.0 and -2982.3 +/- 5.2 kJ mol-1 respectively) have been measured in a rotating bomb calorimeter.The standard enthalpies of formation of these substances in the liquid and the gaseous state have been calculated.
- Zhogina, E. V.,Papina, T. S.,Kolesov, V. P.,Gervits, L. L.,Makarov, K. N.,Vorob'eva, V. P.
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p. 1514 - 1517
(2007/10/02)
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- REACTIONS INVOLVING FLUORIDE ION. PART 34. STABLE PERFLUORINATED CARBANIONS
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A remarkable series of perfluoroalkyl anions, generated by reaction of caesium fluoride with various perfluorinated alkenes have been observed by (19)F and (13)C n.m.r. spectroscopy.Trapping experiments are described and threshold temperatures are established for the onset of fluoride ion exchange.The effects of counter ions are compared and (Me2N)3S+ (TAS) salts are more readily produced than Cs+ salts, but exchange of fluoride ion with fluorinated alkenes occurs more readily with TAS salts.Ph4P+ and Bu4N+ salts could not be obtained.Competition experiments for CsF between various perfluoroalkenes has established orders of carbanion stability.
- Bayliff, Andrew E.,Chambers, Richard D.
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p. 201 - 208
(2007/10/02)
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- SYNTHESIS AND CHEMISTRY OF PERFLUORO-2-IODO-2-METHYL-ALKANES
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Two novel perfluoro-tert-alkyl iodides CF3(CF2)n+1C(CF3)2I have been obtained from F-alkenes CF3(CF2)n-CF=C(CF3)2 (n = 0 and 1) by formal additions of iodine fluoride; these required substantial alterations of known procedures.The F-tert-alkyl iodides are the most reactive alkyl halides known so far, and they are also very toxic.The following types of reactions have been studied: (a) Nucleophilic attack of anions at the iodine, leading to F-alkenes, (b) elimination of iodine fluoride, caused by metals or metal complexes, (c) pyrolysis, to give very selectively F-isobutene and n-perfluoroalkyl iodides, (d) photolysis, and (e) thermally induced insertions into the carbon-iodine bond.Screening results on the inhalation toxicity of the iodides and of some other fluoro-compounds are also reported.
- Probst, A.,Raab, K.,Ulm, K.,Werner, K. von
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p. 223 - 246
(2007/10/02)
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- Reaction of Pyridinium t-Butoxycarbonylmethylide with Perfluoropropene and with Some Fluoroaromatic Compounds: Synthesis of Some Fluorinated Indolizines
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Pyridinium t-butoxycarbonylmethylide (3) reacts with pentafluoropyridine, 3-chlorotetrafluoropyridine, 3,5-dichlorotrifluoropyridine, and octafluorotoluene in the presence of sodium hydride to give pyridinium t-butoxycarbonyl-(perhalogenoaryl)methylides (C5H5NC(CO2But)ArF, ArF = C5F4N, C5ClF3N, C5Cl2F2N, and C6F4CF3 respectively) via nucleophilic displacement of a 4-fluorine substituent in each case.Treatment of perfluoropropene with methylide 3 led to the isolation of 3-(t-butoxycarbonyl)-2-fluoro-1-(trifluoromethyl)indolizine, 1,3-bis(t-butoxycarbonyl)-2-(1,2,2,2-tetrafluoroethyl)indolizine, and a compound believed to be 3-(t-butoxycarbonyl)-2--1-(trifluoromethyl)indolizine.
- Banks, Ronald Eric,Thomson, Julie
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p. 671 - 689
(2007/10/02)
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- Fluoro-olefin Chemistry. Part 19. Reactions of Some Halogenomethylenecyclopropanes
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1,1-Dichloro-2-methylenecyclopropane, 1,1-difluoro-2-methylenecyclopropane, and difluoromethylenecyclopropane all undergo clean addition of bromine to the double bond, without ring opening.In contrast, perfluoro(1-methylene-2,2-dimethylcyclopropane) (4a) and 1-dichlomethylenedecafluoro(2,2-dimethylcyclopropane) (4b) react with bromine and chlorine by ring-opening addition across C1-C2 of the cyclopropane ring to give 2,4-dihalogenopent-1-enes; the double bond may then undergo further addition of chlorine if an excess is present.Photochemical reactions of (4b) with hydrogen bromide and with trifluoroiodomethane give complex reaction mixtures in which ring opening at C1-C2 predominates.Nucleophiles attack perfluoro(1-methylene-2,2-dimethylcyclopropane) at the =CF2 group.Methanol and ethanol give the corresponding ethers; dimethylamine gives the amide, and water the carboxylic acid, by loss of HF from the initial adducts followed by hydrolysis.Attack by fluoride ion in formamide results in HF addition to the double bond, but in an aprotic solvent, rearrangement to a cyclopropene or dimerisation results.The dichloromethylenecyclopropane did not undergo reactions with nucleophiles under comparable conditions.
- Fields, Roy,Haszeldine, Robert N.,Pradhan, Prakash R.,Bunegar, Michael J.
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p. 1217 - 1246
(2007/10/02)
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- SYNTHESIS AND REACTIONS OF THE OXIDES OF HEXAFLUOROPROPYLENE TRIMERS
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By the oxidation of the hexafluoropropylene trimers with an aqueous solution of sodium hypochlorite in the presence of acetonitrile the following α-oxides were obtained: 2,3-Epoxyperfluoro-3-isopropyl-4-methylpentane and 2,3-epoxyperofluoro-3-ethyl-2,4-dimethylpentane.According to the 19F NMR data, the epoxidation takes place stereoselectively with the formation of only one conformer of the α-oxide in each case.The determining effect of the steric factors on the reactivity of the oxides of hexafluoropropylene trimers in reaction with nucleophiles was demonstrated.
- Zapevalov, A. Ya.,Filyakova, T. I.,Peschanskii, N. V.,Kodess, M. I.,Kolenko, I. P.
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p. 1933 - 1938
(2007/10/02)
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- ?-BIS(BENZENE)CHROMIUM(0)-CATALYZED OLIGOMERIZATION OF PERFLUOROPROPYLENE
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In the presence of zerovalent ?-bis(benzene)chromium(0) (I), perfluoropropylene (II) was found to undergo oligomerization under very mild conditions to dimers (b.p. 46 deg, M+, 300) and trimers (b.p. 100-102 deg C, M+ - 19, 431) in the ratio of 2.5-3.0 to 1.One mol of metal complex could catalyze the conversion of 50 mol of perfluoropropylene.One the basis of 19F NMR, the structures of the dimers are III and IV in a ratio of ca. 80/20 and the trimers V and VI; VII and VIII also seemed to be present.V/VI/(VII + VIII) is 80/10/4.In benzene solution, perfluoropropylene was shown not to be catalytically oligomerized by fluoride ion (KF, CrF2 of (CH3)4NF) (nor by monovalent ?-dibenzenechromium(I).A possible mechanism of the reaction was proposed.
- Huang, Yaozeng,Li, Jisen,Zhou, Jianqiang,Zhu, Zhongmu,Hou, Guoyu
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p. 185 - 191
(2007/10/02)
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- Fluoroketenes. 10. Synthesis and Chemistry of a Perfluoroacylketene and a Related Perfluorovinyl Ketone
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The synthesis and chemistry of a perfluoroacylketene (12) and a related perfluorovinyl ketone (5) are described.Both are prepared in good yields from a dimer of hexafluoropropene (2).They are thermally stable but very reactive.No acylketene has previously been isolated.Both compounds give the same hydrolysis product and the same product from dimethylformamide.The vinyl ketone, like previously reported perfluoroacryloyl fluorides, is subject to nucleophilic attack at the terminal unsaturated carbon and reacts as a diene in Diels-Alder additions to C=C, C C, C=N, C N, and C=O unsaturation.The acylketene also reacts as a diene togive adducts that are hydrolysis products of the vinyl ketone adducts.
- England, David C.
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p. 147 - 153
(2007/10/02)
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