GB1159906A - New Ruthenim Complexes and Processes for their Preparation. - Google Patents
New Ruthenim Complexes and Processes for their Preparation.Info
- Publication number
- GB1159906A GB1159906A GB1405968A GB1405968A GB1159906A GB 1159906 A GB1159906 A GB 1159906A GB 1405968 A GB1405968 A GB 1405968A GB 1405968 A GB1405968 A GB 1405968A GB 1159906 A GB1159906 A GB 1159906A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ruthenium
- diket
- formula
- ligand
- complex
- 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
- 239000003446 ligand Substances 0.000 abstract 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229910052707 ruthenium Inorganic materials 0.000 abstract 6
- 239000002904 solvent Substances 0.000 abstract 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 150000002430 hydrocarbons Chemical class 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 239000012327 Ruthenium complex Substances 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- 239000012190 activator Substances 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 150000003303 ruthenium Chemical class 0.000 abstract 2
- IYWJIYWFPADQAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;ruthenium Chemical compound [Ru].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O IYWJIYWFPADQAN-LNTINUHCSA-N 0.000 abstract 1
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 abstract 1
- MUNGMRPYTCHBFX-UHFFFAOYSA-N 1,5-diphenylpentane-1,3,5-trione Chemical compound C=1C=CC=CC=1C(=O)CC(=O)CC(=O)C1=CC=CC=C1 MUNGMRPYTCHBFX-UHFFFAOYSA-N 0.000 abstract 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 abstract 1
- OEKATORRSPXJHE-UHFFFAOYSA-N 2-acetylcyclohexan-1-one Chemical compound CC(=O)C1CCCCC1=O OEKATORRSPXJHE-UHFFFAOYSA-N 0.000 abstract 1
- UYQMAGRFYJIJOQ-UHFFFAOYSA-N 4,4,4-trifluoro-1-naphthalen-1-ylbutane-1,3-dione Chemical compound C1=CC=C2C(C(=O)CC(=O)C(F)(F)F)=CC=CC2=C1 UYQMAGRFYJIJOQ-UHFFFAOYSA-N 0.000 abstract 1
- KHZGUWAFFHXZLC-UHFFFAOYSA-N 5-methylhexane-2,4-dione Chemical compound CC(C)C(=O)CC(C)=O KHZGUWAFFHXZLC-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002879 Lewis base Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical group [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 abstract 1
- LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000539 dimer Substances 0.000 abstract 1
- ILPNRWUGFSPGAA-UHFFFAOYSA-N heptane-2,4-dione Chemical compound CCCC(=O)CC(C)=O ILPNRWUGFSPGAA-UHFFFAOYSA-N 0.000 abstract 1
- DGCTVLNZTFDPDJ-UHFFFAOYSA-N heptane-3,5-dione Chemical compound CCC(=O)CC(=O)CC DGCTVLNZTFDPDJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- ZQOHAQBXINVHHC-UHFFFAOYSA-N hex-2-enedinitrile Chemical class N#CCCC=CC#N ZQOHAQBXINVHHC-UHFFFAOYSA-N 0.000 abstract 1
- NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 150000007527 lewis bases Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003003 phosphines Chemical group 0.000 abstract 1
- 229920000768 polyamine Polymers 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 abstract 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical group [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1895—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing arsenic or antimony
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/20—Carbonyls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
- B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,159,906. Ruthenium complexes; organometallic compounds. RHONE-POULENC S.A. 22 March, 1968 [23 March, 1967; 11 April, 1967; 29 June, 1967; 11 Dec., 1967], No. 14059/68. Headings C2C and C2J. Novel ruthenium complexes are of the formula in which Diket represents a #-diketone residue, L represents a mono- or poly-dentate ligand other than a #-diketone, x and z are positive integers, y is zero or a positive integer and x+y+z=3. The residue Diket is preferably the residue of formula in which R<SP>1</SP> and R<SP>3</SP> are each 1-4 carbon alkyl, 1-4 carbon perfluoroalkyl, phenyl or naphthyl, R<SP>2</SP> is hydrogen or 1-4 carbon alkyl, and R<SP>1</SP> and R<SP>3</SP>, or R<SP>1</SP> and R<SP>2</SP>, or both R<SP>1</SP> and R<SP>2</SP> and R<SP>2</SP> and R<SP>3</SP> may be joined together to form a saturated cycloaliphatic 5- or 6-membered ring. Examples of such #-diketones include acetylacetone, 2,4-hexanedione, 2,4-heptanedione, 5 - methyl - 2,4 - hexanedione; 3,5 - heptanedione; 1,1,1 - trifluoro - 2,4 - pentanedione, benzoylacetone, dibenzoylacetone, 1 - naphthoyl - 3,3,3 - trifluoropropane - 2 - one, 1,3- cyclopentanedione, 1,3 - cyclohexanedione, 2 - acetylcyclohexanone and 1,8 - decahydronaphthalenedione. The ligand L may be taken from Lewis bases which include polyamines and monoamines, aldehydes, imines, amides, nitriles, tertiary phosphines, arsines and stibines, monoolefinic or polyolefinic compounds and heterocyclic bases. The compounds in which x=1, y=0 and z=2 may be obtained by reacting a tris-(#-dionato) ruthenium complex of formula Ru(Diket) 3 with a compound capable of furnishing a carbonyl group such as alcohols, amides, aldehydes and acid chlorides, in the presence of an inert hydrocarbon solvent and at a temperature between 20‹ and 200‹ C. The compounds in which x=y=z=1 may be prepared by reacting a ligand L with a #-dionatoruthenium carbonyl complex of formula [Ru(Diket) 2 (CO)] 2 or by replacing the ligand L<SP>1</SP> in a complex of formula [Ru(Diket) 2 (CO)L<SP>1</SP>] by another ligand L having a greater ability to donate an electron pair, in each case using a hydrocarbon or excess ligand as solvent. The compounds in which x=2, y=0 and z= 1 may be prepared by reacting a tris-(#-dionato) ruthenium of the formula Ru(Diket) 3 with carbon monoxide under a pressure of 5 to 100 bars in the presence of a hydrocarbon or an ether solvent and advantageously containing a ruthenium activator such as hydrated ruthenium oxide, a ruthenium carbonyl or finely divided metallic ruthenium optionally deposited on a carrier, which activator, expressed as ruthenium, is preferably present in a quantity equal to 0À001 to 10% of the weight of ruthenium in the original tris-(#-dionato) ruthenium complex. The compounds of formula [Ru(Diket) 2 (CO) 2 ] may also be prepared by reacting any one of the complexes of formulµ [Ru(Diket) 2 (CO)] 2 ; [Ru(Diket) 2 (CO)L] or [Ru(Diket) 2 L 2 ] with carbon monoxide under at least atmospheric pressure and preferably under 5 to 100 bars in the presence of a hydrocarbon or an ether solvent. The complex of formula Ru(Diket) 2 L 2 may be prepared by reacting a ligand L with a tris-(#-dionato) ruthenium complex under a hydrogen atmosphere and in the presence of a hydrogenation catalyst, particularly ruthenium based, optionally in the presence of a solvent. The #-diketone used in the examples is acetylacetone. In Example 1 ruthenium acetylacetonate is prepared by refluxing RuCl 3 with acetylacetone and water keeping the pH at 7 by addition of sodium bicarbonate. In Example 3, the complex Ru(C 5 H 7 O 2 ) 2 (CO)(CH 3 CN) is reacted with acrylonitrile (stabilized with 0À05% of hydroquinone) under constant hydrogen pressure and a mixture of linear dimers, 1,4-dicyanobutenes and adiponitrile are formed.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR100058A FR1540346A (en) | 1967-03-23 | 1967-03-23 | New ruthenium complexes and their preparation |
| FR102292A FR1526197A (en) | 1967-04-11 | 1967-04-11 | New ruthenium complexes and their preparation |
| FR112456A FR1537041A (en) | 1967-06-29 | 1967-06-29 | New ruthenium complexes and processes for their production |
| FR131735A FR93712E (en) | 1967-06-29 | 1967-12-11 | New ruthenium complexes and methods of obtaining them. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1159906A true GB1159906A (en) | 1969-07-30 |
Family
ID=27444777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1405968A Expired GB1159906A (en) | 1967-03-23 | 1968-03-22 | New Ruthenim Complexes and Processes for their Preparation. |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE712675A (en) |
| BR (1) | BR6897732D0 (en) |
| GB (1) | GB1159906A (en) |
| LU (1) | LU55743A1 (en) |
| NL (1) | NL6803738A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113880705A (en) * | 2021-11-03 | 2022-01-04 | 中国船舶重工集团公司第七一八研究所 | Method for preparing tris (2,4-pentanedionato) ruthenium |
-
1968
- 1968-03-15 NL NL6803738A patent/NL6803738A/xx unknown
- 1968-03-19 BR BR19773268A patent/BR6897732D0/en unknown
- 1968-03-22 LU LU55743D patent/LU55743A1/xx unknown
- 1968-03-22 GB GB1405968A patent/GB1159906A/en not_active Expired
- 1968-03-22 BE BE712675D patent/BE712675A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113880705A (en) * | 2021-11-03 | 2022-01-04 | 中国船舶重工集团公司第七一八研究所 | Method for preparing tris (2,4-pentanedionato) ruthenium |
| CN113880705B (en) * | 2021-11-03 | 2023-07-14 | 中国船舶重工集团公司第七一八研究所 | Method for preparing tris (2, 4-pentanedione) ruthenium |
Also Published As
| Publication number | Publication date |
|---|---|
| BE712675A (en) | 1968-09-23 |
| DE1768029A1 (en) | 1972-01-13 |
| NL6803738A (en) | 1968-09-24 |
| BR6897732D0 (en) | 1973-04-10 |
| LU55743A1 (en) | 1968-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |