EP1494982A1 - Verfahren zur perfluoralkylierung mittels tris(perfluoralkyl)phosphinoxiden - Google Patents
Verfahren zur perfluoralkylierung mittels tris(perfluoralkyl)phosphinoxidenInfo
- Publication number
- EP1494982A1 EP1494982A1 EP03714833A EP03714833A EP1494982A1 EP 1494982 A1 EP1494982 A1 EP 1494982A1 EP 03714833 A EP03714833 A EP 03714833A EP 03714833 A EP03714833 A EP 03714833A EP 1494982 A1 EP1494982 A1 EP 1494982A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- perfluoroalkyl
- perfluoroalkylation
- tris
- phosphine oxide
- pages
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000007983 Tris buffer Substances 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims abstract description 13
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title abstract description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 title abstract 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 16
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000004795 grignard reagents Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 229910052731 fluorine Inorganic materials 0.000 description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- -1 organofluorine compounds Chemical class 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- GFEQDHMENQAHKI-UHFFFAOYSA-N 1-[bis(1,1,2,2,2-pentafluoroethyl)phosphoryl]-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)P(=O)(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)F GFEQDHMENQAHKI-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004293 19F NMR spectroscopy Methods 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000000269 nucleophilic effect Effects 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- QOBLARAJKUCHMF-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1,1-diphenylpropan-1-ol Chemical compound C=1C=CC=CC=1C(C(F)(F)C(F)(F)F)(O)C1=CC=CC=C1 QOBLARAJKUCHMF-UHFFFAOYSA-N 0.000 description 2
- 238000004679 31P NMR spectroscopy Methods 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- HEJQMLUVXZXFRS-UHFFFAOYSA-N difluoro-tris(1,1,2,2,2-pentafluoroethyl)-$l^{5}-phosphane Chemical compound FC(F)(F)C(F)(F)P(F)(F)(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)F HEJQMLUVXZXFRS-UHFFFAOYSA-N 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 2
- 238000006692 trifluoromethylation reaction Methods 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- CBXRMKZFYQISIV-UHFFFAOYSA-N 1-n,1-n,1-n',1-n',2-n,2-n,2-n',2-n'-octamethylethene-1,1,2,2-tetramine Chemical group CN(C)C(N(C)C)=C(N(C)C)N(C)C CBXRMKZFYQISIV-UHFFFAOYSA-N 0.000 description 1
- 238000004607 11B NMR spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000001897 boron-11 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
Definitions
- the present invention relates to a process for perfluoroalkylation using tris (perfluoroalkyl) phosphine oxides.
- Perfluoroalkylation is an important process for the preparation of fluorine-containing compounds, in particular organofluorine compounds. Perfluoroalkylation reagents are usually used
- Perfluoroalkyl halides especially perfluoroalkyl iodides, which act as a source of perfluoroalkyl groups
- Organicfluorine Chemistry. Principles and Commercial Applications Edited by RE Banks, Plenum Press, New York 1994; GG Furin, "Some new aspects in the application of perfluoralkyl halides in the synthesis of fluorine-containing organic compounds "(Review), Russ.Chem.Rev. (English Translation), 69, No. 6 (2000), pages 491-522; NO Brace,” Syntheses with perfluoroalkyl iodides. A review, Part III. ", J.
- perfluoroalkyl halides are used for the preparation of organometallic compounds containing perfluoroalkyl, in particular trifluoromethyl groups, which in turn can be used to introduce perfluoroalkyl groups into organic molecules (DJ Burton, "Fluorinated organometallics: perfluoroalkyl and functionalized perfluoroalkyl organometallic reagents in organic synthesis", Tetrahedron, 48, No. 2 (1992), pages 189-275).
- Trifluoromethylation developed (G.K. Surya Prakash, "Nucleophilic trifluormethylation tamed", J. of Fluorine Chem., 112 (2001), pages 123-131).
- this process of nucleophilic perfluoroalkylation was extended to other organic and inorganic substrates (V.A. Petrov, Tetrahedron Letters, 42 (2001), pages 3267-3269).
- Perfluoroalkylation reagents as described in JR Desmurs et al., 12th European Symposium on Fluorine Chemistry, Berlin, Germany, 1998, Abstracts A23 and A24. However, these reagents can only be produced using CF 3 H, a highly volatile and difficult to handle compound. Furthermore, further stable perfluoroalkylation reagents for nucleophilic triluormethylation have been developed, the synthesis of these reagents starting from the methylhemiketal of fluorais, which has to be prepared beforehand in a relatively complex process. In addition, the application of these reagents to trifluoromethylation limited (G.BIond et al., Tetrahedron Letters, 42 (2001), pages 2437-2475; T.
- the present invention therefore relates to the use of at least one tris (perfluoroalkyl) phosphine oxide for the perfluoroalkylation of chemical substrates.
- Perfluoroalkylphosphinox.de are known. They can be prepared by reacting difluorotris (perfluoroalkyl) phosphoranes with hexamethyldisiloxane [(CH 3 ) 3 Si] 2 0, as described in V.Ya. Semenii et al., Zh. Obshch.Khim., 55, No. 12 (1985), pages 2716-2720.
- the fluorine (perfluoroalkyl) phosphoranes can be prepared by customary methods known to those skilled in the art. These compounds are preferably prepared by electrochemical fluorination of suitable starting compounds, as described in V.Ya. Semenii et al., Zh. Obshch.Khim., 55, No. 12 (1985), pages 2716-2720; N. Igantiev et al, J. of Fluorine Chem., 103 (2000), pages 57-61 and the
- the fluorine (perfluoroalkyl) phosphoranes used as starting compounds can by electrochemical
- Fluorination can be produced inexpensively.
- perfluoroalkylation of chemical substrates with tris (perfluoroalkyl) phosphine oxides it is necessary to add the perfluoroalkylphosphine oxide before or during the reaction with the to treat perfluoroalkylating substrate with at least one base.
- the perfluoroalkylation of the chemical substrate is preferably carried out with at least one tris (perfluoroalkyl) phosphine oxide in the presence of at least one base.
- Strong bases such as, for example, potassium tert-butylate, n-butyllithium, metal amides and / or a Grignard reagent, are preferred.
- the perfluoroalkylation is preferably carried out in a suitable reaction medium which may have been dried by customary processes, such as, for example, cyclic or aliphatic ether, in particular tetrahydrofuran or diethyl ether.
- Organic compounds in particular triple-coordinated organoboron compounds and organic compounds containing carbonyl groups, are preferred as chemical substrates.
- the organoboron compounds used are preferably tris (C 1 ⁇ ) - alkyl borates, particularly preferably trimethyl borate.
- Preferred carbonyl group-indicating compounds are optionally substituted diaryl ketone compounds, especially benzophenone.
- Perfluralkylation of chemical substrates can preferably be carried out with
- Tris (perfluoroalkyl) phosphine oxides can be carried out under an anhydrous atmosphere, such as dry air, or an inert gas atmosphere, such as argon or nitrogen.
- anhydrous atmosphere such as dry air
- an inert gas atmosphere such as argon or nitrogen.
- tris (perfluoralkyl) phosphine oxides as perfluoroalkylation reagents is particularly advantageous because, unlike many other perfluoroalkylation reagents, these compounds are stable compounds, which enables them to be handled easily and safely.
- the NMR spectra were recorded using a Bruker Avance 300 NMR spectrometer with the following frequencies:
- the mass spectra were measured with an AMD 604 device.
- Reaction mixture treated with 20 cm 3 of a 0.1 N HCl and extracted with diethyl ether (2 x 50 cm 3 ). The extract is washed with water (3 x 20 cm 3 ) and dried over magnesium sulfate. The ether is distilled off and the desired product is crystallized from hexane. 0.42 g of 2,2,3,3,3-pentafluoro-1,1-diphenylpropan-1-ol, a white solid with a melting point of 82-83 ° C., is obtained, corresponding to a yield of 30.0 %, based on the phosphine oxide used.
- Reaction mixture should be kept below -55 ° C.
- the reaction mixture is stirred for one hour at -45 ° C. and 0.96 g (5.27 mmol) of benzophenone in 5 cm 3 of dry tetrahydrofuran are added.
- the mixture is then warmed to room temperature within 2 hours.
- the reaction mixture with 20 cm 3 of a 0.1 N HCl treated and extracted with diethyl ether (2 x 50 cm 3 ).
- the extract is washed with water (3 x 20 cm 3 ) and dried over magnesium sulfate.
- the ether is distilled off and the desired product is crystallized from hexane. 0.55 g of 2,2,3,3,3-pentafluo, 1-diphenylpropan-1-ol, a white solid, is obtained, corresponding to a yield of 36.8%, based on the phosphine oxide used.
- Reaction mixture was stirred at -30 ° C for one hour and brought to room temperature.
- the solvent was distilled off and the residue thus obtained was dissolved in 10 cm 3 of diethyl ether.
- the solution was cooled with an ice bath and 1.2 g of anhydrous hydrogen fluoride (HF) was added.
- the reaction mixture was at one hour
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10216996A DE10216996A1 (de) | 2002-04-16 | 2002-04-16 | Verfahren zur Perfluoralkylierung mittels Tris(perfluoralkyl)phosphinoxiden |
DE10216996 | 2002-04-16 | ||
PCT/EP2003/002741 WO2003087020A1 (de) | 2002-04-16 | 2003-03-17 | Verfahren zur perfluoralkylierung mittels tris(perfluoralkyl)phosphinoxiden |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1494982A1 true EP1494982A1 (de) | 2005-01-12 |
Family
ID=28685132
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03714833A Withdrawn EP1494982A1 (de) | 2002-04-16 | 2003-03-17 | Verfahren zur perfluoralkylierung mittels tris(perfluoralkyl)phosphinoxiden |
Country Status (7)
Country | Link |
---|---|
US (1) | US20050119513A1 (de) |
EP (1) | EP1494982A1 (de) |
JP (1) | JP2005522496A (de) |
AU (1) | AU2003219062A1 (de) |
DE (1) | DE10216996A1 (de) |
TW (1) | TW200306982A (de) |
WO (1) | WO2003087020A1 (de) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102712659B (zh) | 2010-01-18 | 2015-09-30 | 默克专利有限公司 | 电解质配制剂 |
US8927757B2 (en) | 2010-01-18 | 2015-01-06 | Merck Patent Gmbh | Process for the preparation of perfluoroalkylcyano- or perfluoroalkylcyanofluoroborates |
AU2011206738A1 (en) | 2010-01-18 | 2012-09-06 | Merck Patent Gmbh | Compounds containing perfluoroalkyl-cyano-alkoxy-borate anions or perfluoroalkyl-cyano-alkoxy-fluoro-borate anions |
DE102010011034A1 (de) * | 2010-03-11 | 2011-09-15 | Merck Patent Gmbh | Verfahren zur Herstellung von Tris (perfluoralkyl)phosphinoxiden |
DE102012013071A1 (de) | 2012-07-02 | 2014-01-02 | Merck Patent Gmbh | Verfahren zur Herstellung von Tris(perfluoralkyl)phosphinoxiden und Bis(perfluoralkyl)phosphinsäuren |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19846636A1 (de) * | 1998-10-09 | 2000-04-13 | Merck Patent Gmbh | Elektrochemische Synthese von Perfluoralkylfluorophosphoranen |
-
2002
- 2002-04-16 DE DE10216996A patent/DE10216996A1/de not_active Withdrawn
-
2003
- 2003-03-17 WO PCT/EP2003/002741 patent/WO2003087020A1/de not_active Application Discontinuation
- 2003-03-17 JP JP2003583979A patent/JP2005522496A/ja active Pending
- 2003-03-17 US US10/511,156 patent/US20050119513A1/en not_active Abandoned
- 2003-03-17 AU AU2003219062A patent/AU2003219062A1/en not_active Abandoned
- 2003-03-17 EP EP03714833A patent/EP1494982A1/de not_active Withdrawn
- 2003-04-14 TW TW092108549A patent/TW200306982A/zh unknown
Non-Patent Citations (1)
Title |
---|
See references of WO03087020A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2005522496A (ja) | 2005-07-28 |
TW200306982A (en) | 2003-12-01 |
DE10216996A1 (de) | 2003-10-30 |
US20050119513A1 (en) | 2005-06-02 |
AU2003219062A1 (en) | 2003-10-27 |
WO2003087020A1 (de) | 2003-10-23 |
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