JP2000507239A - ヘテロ環式カルベンの製造方法 - Google Patents
ヘテロ環式カルベンの製造方法Info
- Publication number
- JP2000507239A JP2000507239A JP9533129A JP53312997A JP2000507239A JP 2000507239 A JP2000507239 A JP 2000507239A JP 9533129 A JP9533129 A JP 9533129A JP 53312997 A JP53312997 A JP 53312997A JP 2000507239 A JP2000507239 A JP 2000507239A
- Authority
- JP
- Japan
- Prior art keywords
- residue
- mmol
- groups
- nmr
- ppm
- 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.)
- Ceased
Links
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 43
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 80
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 150000001412 amines Chemical class 0.000 claims abstract description 18
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 125000004429 atom Chemical group 0.000 claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 105
- -1 metal complex salt anion Chemical class 0.000 claims description 66
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 52
- 229910021529 ammonia Inorganic materials 0.000 claims description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000707 boryl group Chemical group B* 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 150000003458 sulfonic acid derivatives Chemical group 0.000 claims description 2
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003943 azolyl group Chemical group 0.000 claims 1
- 125000000837 carbohydrate group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- FEMRXDWBWXQOGV-UHFFFAOYSA-N potassium amide Chemical class [NH2-].[K+] FEMRXDWBWXQOGV-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 40
- 239000002904 solvent Substances 0.000 description 34
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 24
- 238000003756 stirring Methods 0.000 description 21
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000010948 rhodium Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 14
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 14
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 230000005595 deprotonation Effects 0.000 description 10
- 238000010537 deprotonation reaction Methods 0.000 description 10
- 238000004949 mass spectrometry Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 229910052703 rhodium Inorganic materials 0.000 description 9
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 9
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 229910052721 tungsten Inorganic materials 0.000 description 8
- JBOIAZWJIACNJF-UHFFFAOYSA-N 1h-imidazole;hydroiodide Chemical compound [I-].[NH2+]1C=CN=C1 JBOIAZWJIACNJF-UHFFFAOYSA-N 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000010937 tungsten Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000004611 spectroscopical analysis Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000004693 imidazolium salts Chemical class 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- VFTHHFGSRXXNFZ-UHFFFAOYSA-L 1,3-dimethylimidazol-1-ium diiodide Chemical compound [I-].[I-].C[N+]1=CN(C=C1)C.C[N+]1=CN(C=C1)C VFTHHFGSRXXNFZ-UHFFFAOYSA-L 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 4
- FGNXWZNESBMJDB-UHFFFAOYSA-M 1-methyl-3-(2-phenylethyl)imidazol-1-ium;chloride Chemical compound [Cl-].C1=[N+](C)C=CN1CCC1=CC=CC=C1 FGNXWZNESBMJDB-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-SVYQBANQSA-N deuterated tetrahydrofuran Substances [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- JTDDTDXTQHFZST-UHFFFAOYSA-N potassium;imidazol-3-ide Chemical compound [K+].C1=C[N-]C=N1 JTDDTDXTQHFZST-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- ACNNHRDJONEBAU-UHFFFAOYSA-N 1,3-bis(2-ethoxyethyl)imidazolidine-2-thione Chemical compound CCOCCN1CCN(CCOCC)C1=S ACNNHRDJONEBAU-UHFFFAOYSA-N 0.000 description 3
- NCJDDKWHXVXKIQ-UHFFFAOYSA-N 1,3-dicyclohexylimidazolidin-1-ium;chloride Chemical compound [Cl-].C1C[NH+](C2CCCCC2)CN1C1CCCCC1 NCJDDKWHXVXKIQ-UHFFFAOYSA-N 0.000 description 3
- NUXHRJHNSNRMMO-UHFFFAOYSA-N 1-(2-ethoxyethyl)imidazole Chemical compound CCOCCN1C=CN=C1 NUXHRJHNSNRMMO-UHFFFAOYSA-N 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
- 238000004679 31P NMR spectroscopy Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 101150065749 Churc1 gene Proteins 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 102100038239 Protein Churchill Human genes 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001721 carbon Chemical class 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000005588 protonation Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- ARSMIBSHEYKMJT-UHFFFAOYSA-M 1,3-dimethylimidazolium iodide Chemical compound [I-].CN1C=C[N+](C)=C1 ARSMIBSHEYKMJT-UHFFFAOYSA-M 0.000 description 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
- KGWVFQAPOGAVRF-UHFFFAOYSA-N 1-hexylimidazole Chemical class CCCCCCN1C=CN=C1 KGWVFQAPOGAVRF-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- JECOSSASMXAXFV-UHFFFAOYSA-N chloroethane;hydrochloride Chemical compound Cl.CCCl JECOSSASMXAXFV-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OTDKPPZHTSYUFY-UHFFFAOYSA-N 1,2-bis(2-ethoxyethyl)-1h-imidazol-1-ium;chloride Chemical compound [Cl-].CCOCC[NH+]1C=CN=C1CCOCC OTDKPPZHTSYUFY-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- JCTWNCGDPCOQLX-UHFFFAOYSA-M 1,3,4-triphenyl-1,2,4-triazol-4-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C=1N(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=N[N+]=1C1=CC=CC=C1 JCTWNCGDPCOQLX-UHFFFAOYSA-M 0.000 description 1
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 description 1
- ADEAKBPMDSUYCI-HOTGVXAUSA-N 1,3-bis[(1s)-1-phenylethyl]imidazole-2-thione Chemical compound C1([C@H](C)N2C(N([C@@H](C)C=3C=CC=CC=3)C=C2)=S)=CC=CC=C1 ADEAKBPMDSUYCI-HOTGVXAUSA-N 0.000 description 1
- UPJKDKOHHMKJAY-UHFFFAOYSA-M 1,3-dicyclohexylimidazol-1-ium;chloride Chemical compound [Cl-].C1CCCCC1N1C=[N+](C2CCCCC2)C=C1 UPJKDKOHHMKJAY-UHFFFAOYSA-M 0.000 description 1
- LSKGVMCYWOQFJO-UHFFFAOYSA-M 1,3-dihexylimidazol-1-ium bromide Chemical compound [Br-].CCCCCCN1C=C[N+](CCCCCC)=C1 LSKGVMCYWOQFJO-UHFFFAOYSA-M 0.000 description 1
- HLARWPSCENWPHP-UHFFFAOYSA-N 1,3-dihexylimidazolidine-2-thione Chemical compound CCCCCCN1CCN(CCCCCC)C1=S HLARWPSCENWPHP-UHFFFAOYSA-N 0.000 description 1
- IIJSFQFJZAEKHB-UHFFFAOYSA-M 1,3-dimethylimidazol-1-ium;chloride Chemical compound [Cl-].CN1C=C[N+](C)=C1 IIJSFQFJZAEKHB-UHFFFAOYSA-M 0.000 description 1
- MMYKTRPLXXWLBC-UHFFFAOYSA-N 1-bromo-2-ethoxyethane Chemical compound CCOCCBr MMYKTRPLXXWLBC-UHFFFAOYSA-N 0.000 description 1
- GOKUDEWVRNZXDZ-UHFFFAOYSA-N 1-bromo-3-(3-bromopropoxy)propane Chemical compound BrCCCOCCCBr GOKUDEWVRNZXDZ-UHFFFAOYSA-N 0.000 description 1
- 238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 1
- PKKDWPSOOQBWFB-UHFFFAOYSA-N 2,4-dichloro-6-[(3,5-dichloro-2-hydroxyphenyl)methyl]phenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1CC1=CC(Cl)=CC(Cl)=C1O PKKDWPSOOQBWFB-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- MMDFSEGJGPURPF-UHFFFAOYSA-N 2-octyl-1h-imidazole Chemical compound CCCCCCCCC1=NC=CN1 MMDFSEGJGPURPF-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- KRLUIKUPPPXVHO-UHFFFAOYSA-N 2h-triazole;hydroiodide Chemical compound [I-].[NH2+]1C=CN=N1 KRLUIKUPPPXVHO-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- NGKJRIXYLPNWHI-UHFFFAOYSA-M 4-methyl-1-(4-nitrophenyl)-1,2,4-triazol-4-ium;iodide Chemical compound [I-].C1=[N+](C)C=NN1C1=CC=C([N+]([O-])=O)C=C1 NGKJRIXYLPNWHI-UHFFFAOYSA-M 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001436679 Adama Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000295146 Gallionellaceae Species 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 208000012287 Prolapse Diseases 0.000 description 1
- 241001080173 Ridens Species 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical compound [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 description 1
- QOUGMLPYXIXFHK-UHFFFAOYSA-M [Cl-].C(C)NCC[N+]1=CN(C=C1)C Chemical compound [Cl-].C(C)NCC[N+]1=CN(C=C1)C QOUGMLPYXIXFHK-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940099352 cholate Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- LYGJENNIWJXYER-MICDWDOJSA-N deuterio(nitro)methane Chemical compound [2H]C[N+]([O-])=O LYGJENNIWJXYER-MICDWDOJSA-N 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-O hydron;1h-pyrrole Chemical compound [NH2+]1C=CC=C1 KAESVJOAVNADME-UHFFFAOYSA-O 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- PKAUVIXBZJUYRV-UHFFFAOYSA-N methane;hydroiodide Chemical compound C.I PKAUVIXBZJUYRV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical compound S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19610908A DE19610908A1 (de) | 1996-03-20 | 1996-03-20 | Verfahren zur Herstellung heterocyclischer Carbene |
| DE19610908.6 | 1996-03-20 | ||
| PCT/EP1997/001296 WO1997034875A1 (de) | 1996-03-20 | 1997-03-14 | Verfahren zur herstellung heterocyclischer carbene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000507239A true JP2000507239A (ja) | 2000-06-13 |
| JP2000507239A5 JP2000507239A5 (enExample) | 2004-12-02 |
Family
ID=7788826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9533129A Ceased JP2000507239A (ja) | 1996-03-20 | 1997-03-14 | ヘテロ環式カルベンの製造方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6025496A (enExample) |
| EP (1) | EP0888308A1 (enExample) |
| JP (1) | JP2000507239A (enExample) |
| KR (1) | KR100492653B1 (enExample) |
| CN (1) | CN1216536A (enExample) |
| AU (1) | AU710591B2 (enExample) |
| BR (1) | BR9708234A (enExample) |
| CA (1) | CA2250086A1 (enExample) |
| DE (1) | DE19610908A1 (enExample) |
| ID (1) | ID16265A (enExample) |
| PL (1) | PL329010A1 (enExample) |
| TW (1) | TW412530B (enExample) |
| WO (1) | WO1997034875A1 (enExample) |
| ZA (1) | ZA972198B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005239607A (ja) * | 2004-02-25 | 2005-09-08 | Kimoto & Co Ltd | イミダゾールカルベン金属錯体の製造方法 |
| JP2005239606A (ja) * | 2004-02-25 | 2005-09-08 | Kimoto & Co Ltd | イミダゾールカルベン付加体の製造方法 |
| JP2019142829A (ja) * | 2018-02-23 | 2019-08-29 | 東ソー株式会社 | 新規セリウム錯体、及び発光材 |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19815275B4 (de) * | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
| US7285593B1 (en) | 1998-05-19 | 2007-10-23 | Advanced Polymer Technologies, Inc. | Polyolefin compositions optionally having variable toughness and/or hardness |
| FR2778916B1 (fr) | 1998-05-20 | 2000-06-30 | Rhone Poulenc Fibres | Nouveaux complexes organometalliques comprenant des carbenes heterocycliques cationiques et leur procede de preparation |
| GB9814282D0 (en) | 1998-07-01 | 1998-09-02 | Borealis As | Catalysts |
| US6316380B1 (en) * | 1998-09-10 | 2001-11-13 | University Of New Orleans Research & Technology Foundation | Catalyst system comprising transition metal and imidazoline-2-ylidene or imidazolidine-2-ylidene |
| JP5066656B2 (ja) | 1998-09-10 | 2012-11-07 | ユニバーシティ・オブ・ニュー・オーリンズ・リサーチ・アンド・テクノロジー・ファウンデーション・インコーポレーテッド | カルベンリガンドを持った触媒錯体 |
| US6409875B1 (en) | 1999-02-05 | 2002-06-25 | Materia, Inc. | Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces |
| US20140088260A1 (en) | 1999-02-05 | 2014-03-27 | Materia, Inc. | Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces |
| AU779888B2 (en) | 1999-02-05 | 2005-02-17 | Materia, Inc. | Polyolefin compositions having variable density and methods for their production and use |
| JP2002540213A (ja) * | 1999-03-31 | 2002-11-26 | カリフォルニア インスティチュート オブ テクノロジー | 高いオレフィンメタセシス活性を示す、トリアゾールイリデン配位子により配位された新規なルテニウム金属アルキルジエン錯体 |
| US7329758B1 (en) | 1999-05-24 | 2008-02-12 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
| DE10025623A1 (de) * | 2000-05-24 | 2001-12-06 | Bayer Ag | Immobilisierte Palladiumkomplexe |
| WO2002038566A2 (en) * | 2000-11-10 | 2002-05-16 | The University Of Akron | Carbene porphyrins and carbene porphyrinoids for use in medical diagnosis and treatment |
| GB0031078D0 (en) * | 2000-12-20 | 2001-01-31 | Borealis Tech Oy | Compounds |
| US6838489B2 (en) * | 2001-03-23 | 2005-01-04 | Cymetech, Llc | High activity metal carbene metathesis catalysts generated using a thermally activated N-heterocyclic carbene precursor |
| DK1372844T3 (da) * | 2001-03-23 | 2011-04-18 | California Inst Of Techn | Højaktive metalcarbenmetatesekatalysatorer, der er fremstillet ved anvendelse af et termisk aktiveret n-heterocyklisk carbenforstadium |
| AU2003217232A1 (en) | 2002-02-04 | 2003-09-02 | Massachusetts Institute Of Technology | Transition-metal-catalyzed carbon-nitrogen bond-forming methods using carbene ligands |
| CN1835958A (zh) * | 2003-08-11 | 2006-09-20 | 默克专利有限公司 | 可被固定的n－杂环碳烯 |
| US8519146B2 (en) * | 2004-09-07 | 2013-08-27 | The University Of Akron | Metal complexes of N-heterocyclic carbenes as antibiotics |
| EP1660444B1 (en) * | 2003-09-05 | 2014-11-12 | The University of Akron | Metal complexes of n-heterocyclic carbenes as radiopharmaceuticals and antibiotics |
| DE102004060247A1 (de) * | 2004-12-15 | 2006-06-29 | Studiengesellschaft Kohle Mbh | Neue N-heterocyclische Carbene und ihre Anwendung in der Katalyse |
| AU2008260203B2 (en) * | 2007-05-31 | 2013-05-02 | The University Of Akron | Metal complexes incorporated within biodegradable nanoparticles and their use |
| AU2008279309B2 (en) * | 2007-07-23 | 2013-10-31 | The University Of Akron | Metal complexes incorporated within biodegradable nanoparticles and their use |
| AU2010233109B2 (en) * | 2009-04-09 | 2014-10-30 | California Institute Of Technology | Molecular sieves and related methods and structure directing agents |
| AU2010245265B2 (en) | 2009-05-05 | 2014-07-31 | Stepan Company | Sulfonated internal olefin surfactant for enhanced oil recovery |
| EP2261217A1 (en) * | 2009-06-10 | 2010-12-15 | Politecnico di Milano | Imidazolium salts having liquid crystal characteristics, useful as electrolytes |
| US8227371B2 (en) | 2010-09-24 | 2012-07-24 | Exxonmobil Chemical Patents Inc. | Class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof |
| US9181360B2 (en) | 2011-08-12 | 2015-11-10 | Exxonmobil Chemical Patents Inc. | Polymers prepared by ring opening / cross metathesis |
| JP7212409B2 (ja) | 2018-10-10 | 2023-01-25 | コリア リサーチ インスティチュート オブ バイオサイエンス アンド バイオテクノロジー | カルベン化合物、カルベン‐金属ナノ粒子複合体およびその製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4230466A1 (de) * | 1992-09-11 | 1994-03-17 | Basf Ag | Verfahren zur katalytischen Herstellung von Kondensationsprodukten des Formaldehyds |
| DE4447066A1 (de) * | 1994-12-29 | 1996-07-04 | Hoechst Ag | Heterocyclische Carbene enthaltende Metallkomplexverbindungen |
-
1996
- 1996-03-20 DE DE19610908A patent/DE19610908A1/de not_active Withdrawn
-
1997
- 1997-03-05 TW TW086102643A patent/TW412530B/zh active
- 1997-03-13 ID IDP970808A patent/ID16265A/id unknown
- 1997-03-13 ZA ZA9702198A patent/ZA972198B/xx unknown
- 1997-03-14 BR BR9708234A patent/BR9708234A/pt not_active Application Discontinuation
- 1997-03-14 EP EP97915369A patent/EP0888308A1/de not_active Withdrawn
- 1997-03-14 PL PL97329010A patent/PL329010A1/xx unknown
- 1997-03-14 JP JP9533129A patent/JP2000507239A/ja not_active Ceased
- 1997-03-14 CN CN97193968A patent/CN1216536A/zh active Pending
- 1997-03-14 WO PCT/EP1997/001296 patent/WO1997034875A1/de not_active Ceased
- 1997-03-14 CA CA002250086A patent/CA2250086A1/en not_active Abandoned
- 1997-03-14 US US09/155,065 patent/US6025496A/en not_active Expired - Fee Related
- 1997-03-14 KR KR10-1998-0707423A patent/KR100492653B1/ko not_active Expired - Fee Related
- 1997-03-14 AU AU22878/97A patent/AU710591B2/en not_active Ceased
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005239607A (ja) * | 2004-02-25 | 2005-09-08 | Kimoto & Co Ltd | イミダゾールカルベン金属錯体の製造方法 |
| JP2005239606A (ja) * | 2004-02-25 | 2005-09-08 | Kimoto & Co Ltd | イミダゾールカルベン付加体の製造方法 |
| JP2019142829A (ja) * | 2018-02-23 | 2019-08-29 | 東ソー株式会社 | 新規セリウム錯体、及び発光材 |
| JP7100312B2 (ja) | 2018-02-23 | 2022-07-13 | 東ソー株式会社 | 新規セリウム錯体、及び発光材 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0888308A1 (de) | 1999-01-07 |
| CA2250086A1 (en) | 1997-09-25 |
| AU710591B2 (en) | 1999-09-23 |
| ID16265A (id) | 1997-09-18 |
| DE19610908A1 (de) | 1997-09-25 |
| KR20000064700A (ko) | 2000-11-06 |
| ZA972198B (en) | 1997-09-17 |
| WO1997034875A1 (de) | 1997-09-25 |
| TW412530B (en) | 2000-11-21 |
| US6025496A (en) | 2000-02-15 |
| CN1216536A (zh) | 1999-05-12 |
| AU2287897A (en) | 1997-10-10 |
| KR100492653B1 (ko) | 2005-11-11 |
| BR9708234A (pt) | 1999-08-03 |
| PL329010A1 (en) | 1999-03-01 |
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