CA1236483A - Marquage des molecules organiques - Google Patents
Marquage des molecules organiquesInfo
- Publication number
- CA1236483A CA1236483A CA000476816A CA476816A CA1236483A CA 1236483 A CA1236483 A CA 1236483A CA 000476816 A CA000476816 A CA 000476816A CA 476816 A CA476816 A CA 476816A CA 1236483 A CA1236483 A CA 1236483A
- Authority
- CA
- Canada
- Prior art keywords
- nickel
- labelled
- chemical substance
- process according
- deuterium
- 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
- 238000002372 labelling Methods 0.000 title claims abstract description 13
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 26
- 239000000463 material Substances 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 22
- 230000000155 isotopic effect Effects 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 239000002243 precursor Substances 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 46
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000007868 Raney catalyst Substances 0.000 claims description 14
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 11
- 229910052722 tritium Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 27
- 229910052759 nickel Inorganic materials 0.000 claims 11
- 229910045601 alloy Inorganic materials 0.000 claims 1
- 239000000956 alloy Substances 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical class [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract description 24
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 4
- WPYMKLBDIGXBTP-RALIUCGRSA-N 2,3,4,5,6-pentadeuteriobenzoic acid Chemical compound [2H]C1=C([2H])C([2H])=C(C(O)=O)C([2H])=C1[2H] WPYMKLBDIGXBTP-RALIUCGRSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001728 carbonyl compounds Chemical class 0.000 description 3
- 238000006392 deoxygenation reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QWUWMCYKGHVNAV-AREBVXNXSA-N (1,1,2,2-tetradeuterio-2-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C([2H])([2H])C([2H])([2H])C1=CC=CC=C1 QWUWMCYKGHVNAV-AREBVXNXSA-N 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JAGZUIGGHGTFHO-LZMSFWOYSA-N ethyl 2,2,3,3-tetradeuterio-3-phenylpropanoate Chemical compound CCOC(=O)C([2H])([2H])C([2H])([2H])C1=CC=CC=C1 JAGZUIGGHGTFHO-LZMSFWOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- DXIHILNWDOYYCH-UHDJGPCESA-M sodium;(e)-3-phenylprop-2-enoate Chemical compound [Na+].[O-]C(=O)\C=C\C1=CC=CC=C1 DXIHILNWDOYYCH-UHDJGPCESA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- BVHLGVCQOALMSV-FUVXPQFCSA-N (2s)-2,6-diamino-2,6,6-trideuteriohexanoic acid;hydrochloride Chemical compound Cl.[2H]C([2H])(N)CCC[C@]([2H])(N)C(O)=O BVHLGVCQOALMSV-FUVXPQFCSA-N 0.000 description 1
- MTCFGRXMJLQNBG-RBXBQAPRSA-N (2s)-2-amino-2,3,3-trideuterio-3-hydroxypropanoic acid Chemical compound [2H]C([2H])(O)[C@]([2H])(N)C(O)=O MTCFGRXMJLQNBG-RBXBQAPRSA-N 0.000 description 1
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- DHMQDGOQFOQNFH-DICFDUPASA-N 2-amino-2,2-dideuterioacetic acid Chemical compound [2H]C([2H])(N)C(O)=O DHMQDGOQFOQNFH-DICFDUPASA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 241001058146 Erium Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000003635 deoxygenating effect Effects 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229960005337 lysine hydrochloride Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- PVNIIMVLHYAWGP-RHQRLBAQSA-N nicotinic-d4 acid Chemical compound [2H]C1=NC([2H])=C(C(O)=O)C([2H])=C1[2H] PVNIIMVLHYAWGP-RHQRLBAQSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005533 tritiation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU413384 | 1984-03-19 | ||
| AUPG4133/84 | 1984-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1236483A true CA1236483A (fr) | 1988-05-10 |
Family
ID=3694596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000476816A Expired CA1236483A (fr) | 1984-03-19 | 1985-03-18 | Marquage des molecules organiques |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0174962A1 (fr) |
| CA (1) | CA1236483A (fr) |
| WO (1) | WO1985004167A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5565324A (en) * | 1992-10-01 | 1996-10-15 | The Trustees Of Columbia University In The City Of New York | Complex combinatorial chemical libraries encoded with tags |
| US11981613B2 (en) | 2022-01-20 | 2024-05-14 | Battelle Savannah River Alliance, Llc | Hydrogen isotope exchange methods and systems for organic and organosilicon materials |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3864415A (en) * | 1967-04-29 | 1975-02-04 | Frosst & Co Charles E | Novel compounds and method |
| NL163210C (nl) * | 1969-06-06 | 1980-08-15 | Byk Mallinckrodt Cil Bv | Werkwijze voor de bereiding van radioactief seleno- methionine. |
| CA962283A (en) * | 1970-05-08 | 1975-02-04 | Frosst (Charles E.) And Co. | Process for deuterating bromide derivatives |
| US3966781A (en) * | 1970-12-17 | 1976-06-29 | Merck Sharp & Dohme (I.A.) Corporation | Deuteration of functional group-containing hydrocarbons |
| US3859048A (en) * | 1973-06-07 | 1975-01-07 | Pierce Chemical Co | Composition and method for the preparation of deuterated esters of carboxylic acids for gas phase analysis |
| NL7315287A (nl) * | 1973-11-08 | 1975-05-12 | Philips Nv | Methode voor de bepaling van vetresorptie als- mede hierbij toegepaste stoffen en daarvan af- geleide preparaten. |
| US3989705A (en) * | 1974-04-01 | 1976-11-02 | Canadian Patents And Development Limited | Processes for the deuteration and/or tritiation of organic substrates by hydrogen substitution |
| SU560879A1 (ru) * | 1975-10-21 | 1977-06-05 | Ленинградский Ордена Ленина И Ордена Трудового Красного Знамени Государственный Университет Им. А.А.Жданова | Способ получени дейтерированных -диазокарбонильных соединений |
| GB1566330A (en) * | 1977-02-16 | 1980-04-30 | Farmaceutici Italia | Anthracycline glycosides |
| US4154971A (en) * | 1977-06-06 | 1979-05-15 | The Dow Chemical Company | Deuterated 1,1-difluoro-2,2-dihaloethyl difluoromethyl ethers |
| CA1078865A (fr) * | 1977-07-06 | 1980-06-03 | Grant W. Reader | Acides gras marques par un isotope |
| DE2810696C3 (de) * | 1978-03-11 | 1982-02-25 | Kernforschungsanlage Jülich GmbH, 5170 Jülich | Verfahren zur Gewinnung von ω-↑123↑J-Hexadecansäure oder ω↑123↑J-Heptadecansäure und deren Verwendung als Radiopharmaka |
-
1985
- 1985-03-18 CA CA000476816A patent/CA1236483A/fr not_active Expired
- 1985-03-18 WO PCT/AU1985/000054 patent/WO1985004167A1/fr not_active Ceased
- 1985-03-18 EP EP19850901313 patent/EP0174962A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1985004167A1 (fr) | 1985-09-26 |
| EP0174962A1 (fr) | 1986-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |