JPH0415211B2 - - Google Patents
Info
- Publication number
- JPH0415211B2 JPH0415211B2 JP8112981A JP8112981A JPH0415211B2 JP H0415211 B2 JPH0415211 B2 JP H0415211B2 JP 8112981 A JP8112981 A JP 8112981A JP 8112981 A JP8112981 A JP 8112981A JP H0415211 B2 JPH0415211 B2 JP H0415211B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- metal atom
- general formula
- iodonium
- 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.)
- Expired
Links
- -1 perfluoroalkyl compound Chemical class 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- BAFRDXKXMYNVCT-UHFFFAOYSA-N iodobenzene;trifluoromethanesulfonic acid Chemical compound IC1=CC=CC=C1.OS(=O)(=O)C(F)(F)F BAFRDXKXMYNVCT-UHFFFAOYSA-N 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ULAQISQDFQAUCH-UHFFFAOYSA-N trifluoromethanesulfonic acid hydroiodide Chemical compound I.OS(=O)(=O)C(F)(F)F ULAQISQDFQAUCH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- KTNLYTNKBOKXRW-UHFFFAOYSA-N phenyliodanium Chemical compound [IH+]C1=CC=CC=C1 KTNLYTNKBOKXRW-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- RIVYCUREDZYSKA-UHFFFAOYSA-N 1-ethynyl-4-methylbenzene Chemical compound CC1=CC=C(C#[C-])C=C1 RIVYCUREDZYSKA-UHFFFAOYSA-N 0.000 description 1
- RMHIPWMOZZBZCU-UHFFFAOYSA-N 2-nitropropane;potassium Chemical compound [K].CC(C)[N+]([O-])=O RMHIPWMOZZBZCU-UHFFFAOYSA-N 0.000 description 1
- WCNKHTIPPVQEQW-UHFFFAOYSA-N 4,4,4-trifluorobut-1-ene Chemical compound FC(F)(F)CC=C WCNKHTIPPVQEQW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ONFQYRSAKQMQHD-UHFFFAOYSA-N C(CCC)[Cu]CCCC Chemical class C(CCC)[Cu]CCCC ONFQYRSAKQMQHD-UHFFFAOYSA-N 0.000 description 1
- BBDWSLNMVHYJCD-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C[Na] Chemical class C1(=CC=CC=C1)S(=O)(=O)C[Na] BBDWSLNMVHYJCD-UHFFFAOYSA-N 0.000 description 1
- BJVFGWYBOLMUEM-UHFFFAOYSA-M CC(=C)C[Mg]Cl Chemical compound CC(=C)C[Mg]Cl BJVFGWYBOLMUEM-UHFFFAOYSA-M 0.000 description 1
- HSSAUTCKFNBPAS-UHFFFAOYSA-N CCCC[Cu] Chemical class CCCC[Cu] HSSAUTCKFNBPAS-UHFFFAOYSA-N 0.000 description 1
- RIPZMSTYGQPOIZ-UHFFFAOYSA-N CS(=O)(=O)O.IC1=CC=CC=C1 Chemical compound CS(=O)(=O)O.IC1=CC=CC=C1 RIPZMSTYGQPOIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005997 Calcium carbide Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZTVPVJDIVHSMSI-UHFFFAOYSA-M Cl[Mg]C(C=C)c1ccccc1 Chemical compound Cl[Mg]C(C=C)c1ccccc1 ZTVPVJDIVHSMSI-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- JFJZZFHRBKGKAE-UHFFFAOYSA-M [Br-].CC(C)(C)OC(=O)C[Zn+] Chemical compound [Br-].CC(C)(C)OC(=O)C[Zn+] JFJZZFHRBKGKAE-UHFFFAOYSA-M 0.000 description 1
- ZPUGFZPCSRCLTF-UHFFFAOYSA-M [Cl-].[Mg+]C#CC1=CC=CC=C1 Chemical compound [Cl-].[Mg+]C#CC1=CC=CC=C1 ZPUGFZPCSRCLTF-UHFFFAOYSA-M 0.000 description 1
- SNIYGPDAYLBEMK-UHFFFAOYSA-M [I-].[Mg+]C1=CC=CC=C1 Chemical compound [I-].[Mg+]C1=CC=CC=C1 SNIYGPDAYLBEMK-UHFFFAOYSA-M 0.000 description 1
- DPWMKSJSGYEXBN-UHFFFAOYSA-M [K+].[I-].OS(O)(=O)=O Chemical compound [K+].[I-].OS(O)(=O)=O DPWMKSJSGYEXBN-UHFFFAOYSA-M 0.000 description 1
- SSLUBYUKDKZZPS-UHFFFAOYSA-N [Li]C1SCCCS1 Chemical compound [Li]C1SCCCS1 SSLUBYUKDKZZPS-UHFFFAOYSA-N 0.000 description 1
- HGUBCLCSMVFWKM-UHFFFAOYSA-N [Li]C=COCC Chemical compound [Li]C=COCC HGUBCLCSMVFWKM-UHFFFAOYSA-N 0.000 description 1
- LZBWYSNPIAOGJG-UHFFFAOYSA-N [Li]C=Cc1ccccc1 Chemical compound [Li]C=Cc1ccccc1 LZBWYSNPIAOGJG-UHFFFAOYSA-N 0.000 description 1
- CJKOYHIJFXXCBB-UHFFFAOYSA-N [N+](=O)([O-])CC.[Na] Chemical compound [N+](=O)([O-])CC.[Na] CJKOYHIJFXXCBB-UHFFFAOYSA-N 0.000 description 1
- SCCZRLUBHULEKH-UHFFFAOYSA-M [Na+].[I-].OS(O)(=O)=O Chemical compound [Na+].[I-].OS(O)(=O)=O SCCZRLUBHULEKH-UHFFFAOYSA-M 0.000 description 1
- XHRNWLQQVSYTDD-UHFFFAOYSA-N [Na].C[N+]([O-])=O Chemical compound [Na].C[N+]([O-])=O XHRNWLQQVSYTDD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VQNPSCRXHSIJTH-UHFFFAOYSA-N cadmium(2+);carbanide Chemical compound [CH3-].[CH3-].[Cd+2] VQNPSCRXHSIJTH-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- PDQYDAMNFMHSJS-UHFFFAOYSA-N diethyl propanedioate;sodium Chemical compound [Na].CCOC(=O)CC(=O)OCC PDQYDAMNFMHSJS-UHFFFAOYSA-N 0.000 description 1
- ATZBPOVXVPIOMR-UHFFFAOYSA-N dimethylmercury Chemical compound C[Hg]C ATZBPOVXVPIOMR-UHFFFAOYSA-N 0.000 description 1
- KZXVOMYVNQPCKX-UHFFFAOYSA-N ethyne;mercury(1+) Chemical compound [Hg+].[C-]#C KZXVOMYVNQPCKX-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- QNTMIZIPMDGYSA-UHFFFAOYSA-M hydrogen sulfate;1,1,2,2,2-pentafluoroethyl(phenyl)iodanium Chemical compound OS([O-])(=O)=O.FC(F)(F)C(F)(F)[I+]C1=CC=CC=C1 QNTMIZIPMDGYSA-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- WGKCQDKOABJRQO-UHFFFAOYSA-N iodobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.IC1=CC=CC=C1 WGKCQDKOABJRQO-UHFFFAOYSA-N 0.000 description 1
- XHEHDQPARIPMRX-UHFFFAOYSA-N lithium;dioxido(propan-2-ylidene)azanium Chemical compound [Li+].CC(C)=[N+]([O-])[O-] XHEHDQPARIPMRX-UHFFFAOYSA-N 0.000 description 1
- PEVVNTJHQRSIIP-UHFFFAOYSA-N lithium;methanidylsulfanylbenzene Chemical class [Li+].[CH2-]SC1=CC=CC=C1 PEVVNTJHQRSIIP-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 1
- DHZDXXLCWXHNOB-UHFFFAOYSA-M magnesium;ethylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]CC1=CC=CC=C1 DHZDXXLCWXHNOB-UHFFFAOYSA-M 0.000 description 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- YAMQOOCGNXAQGW-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=CC=[C-]1 YAMQOOCGNXAQGW-UHFFFAOYSA-M 0.000 description 1
- HQDAZWQQKSJCTM-UHFFFAOYSA-M magnesium;octane;chloride Chemical compound [Mg+2].[Cl-].CCCCCCC[CH2-] HQDAZWQQKSJCTM-UHFFFAOYSA-M 0.000 description 1
- WQMNNHNWITXOAH-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].CC=[CH-] WQMNNHNWITXOAH-UHFFFAOYSA-M 0.000 description 1
- CYSFUFRXDOAOMP-UHFFFAOYSA-M magnesium;prop-1-ene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C=C CYSFUFRXDOAOMP-UHFFFAOYSA-M 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HZOAWXQTMQXJBS-UHFFFAOYSA-N methyl 2-cyanoacetate;sodium Chemical compound [Na].COC(=O)CC#N HZOAWXQTMQXJBS-UHFFFAOYSA-N 0.000 description 1
- UVFNLZOPNNHSFA-UHFFFAOYSA-N methyl hydrogen sulfate;hydroiodide Chemical compound I.COS(O)(=O)=O UVFNLZOPNNHSFA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- ZAEONNWVHYAONP-UHFFFAOYSA-M phenyl(trifluoromethyl)iodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.FC(F)(F)[I+]C1=CC=CC=C1 ZAEONNWVHYAONP-UHFFFAOYSA-M 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- SLERPCVQDVNSAK-UHFFFAOYSA-N silver;ethyne Chemical compound [Ag+].[C-]#C SLERPCVQDVNSAK-UHFFFAOYSA-N 0.000 description 1
- HAYHIDZXMABSNY-UHFFFAOYSA-N sodium dioxido(propan-2-ylidene)azanium Chemical compound [Na+].CC(C)=[N+]([O-])[O-] HAYHIDZXMABSNY-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- OHUVHDUNQKJDKW-UHFFFAOYSA-N sodium;cyclopenta-1,3-diene Chemical compound [Na+].C=1C=C[CH-]C=1 OHUVHDUNQKJDKW-UHFFFAOYSA-N 0.000 description 1
- WUAWDNVSABPBSI-UHFFFAOYSA-N sodium;ethynylbenzene Chemical compound [Na+].[C-]#CC1=CC=CC=C1 WUAWDNVSABPBSI-UHFFFAOYSA-N 0.000 description 1
- VEWVOZQEDLJGOU-UHFFFAOYSA-N sulfurofluoridic acid hydroiodide Chemical compound OS(F)(=O)=O.I VEWVOZQEDLJGOU-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
- ZTCGGBIFOFASKI-UHFFFAOYSA-N tert-butyl acetate;lithium Chemical compound [Li].CC(=O)OC(C)(C)C ZTCGGBIFOFASKI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8112981A JPS57197234A (en) | 1981-05-29 | 1981-05-29 | Preparation of perfluoroalkyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8112981A JPS57197234A (en) | 1981-05-29 | 1981-05-29 | Preparation of perfluoroalkyl compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57197234A JPS57197234A (en) | 1982-12-03 |
| JPH0415211B2 true JPH0415211B2 (enrdf_load_stackoverflow) | 1992-03-17 |
Family
ID=13737778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8112981A Granted JPS57197234A (en) | 1981-05-29 | 1981-05-29 | Preparation of perfluoroalkyl compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57197234A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7553985B2 (en) | 2005-11-02 | 2009-06-30 | E.I. Du Pont De Nemours And Company | Fluorinated surfactants |
-
1981
- 1981-05-29 JP JP8112981A patent/JPS57197234A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57197234A (en) | 1982-12-03 |
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