JP2000506888A - 水溶液中でのアルキンの環状三量化法 - Google Patents
水溶液中でのアルキンの環状三量化法Info
- Publication number
- JP2000506888A JP2000506888A JP9533471A JP53347197A JP2000506888A JP 2000506888 A JP2000506888 A JP 2000506888A JP 9533471 A JP9533471 A JP 9533471A JP 53347197 A JP53347197 A JP 53347197A JP 2000506888 A JP2000506888 A JP 2000506888A
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- 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
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2291—Olefins
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- 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
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/44—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon double or triple bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
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- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
- B01J2231/328—Cycloadditions involving more than 2 components or moieties, e.g. intra-/intermolecualar [2+2+2] or [2+2+1], e.g. Pauson-Khand type
-
- 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
- B01J2531/822—Rhodium
-
- 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
- B01J2531/827—Iridium
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- 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
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
-
- 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
- B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
- B01J2531/96—Water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 同一のまたは異なるアルキン3分子から水溶液中で芳香族化合物を製造す る方法であって、 一般式 Rx−C−M−L 〔式中、Cはシクロペンタジエニルまたはインデニル基を表し; Rはニトリル、エステル、ケトン、アミド、クロロ、またはフルオロからなる 群から選ばれる電子求引基であり、 X=0,1または2; MはCo,Rh,またはIrからなる群から選ばれる遷移金属であり、 Lは遷移金属の2個の別個の2電子π−配位子または1個の4電子π−配位子 からなる群から選ばれる配位子である〕 の水溶性遷移金属触媒を調製する工程; 前記アルキンを前記水溶性遷移金属触媒の存在下で反応させる工程;および 前記芳香族化合物を単離し精製する工程; を備えた、上記方法。 2. 前記アルキンの各々が独立に構造: 〔式中、R1およびR2は水素、アルコール、エーテル、ケトン、エステル、ア ミド、アミン、スルフィド、サルフェート、ホスフェート、C1−C20アルカン 、置換C1−C20アルカン、ハロゲン、芳香族、複素環式芳香族、チオエーテル またはチオエステルから独立に選ばれる官能基である〕 を有する、請求項1記載の方法。 3. R1およびR2が、H、C1からC5アルコール、C1からC5ケトン、C1か らC5エステルまたはC1からC5アミンからなる群から独立に選ばれる、請求項 2記載の方法。 4. R1およびR2が、それぞれH,−CH2OH,−COCH3, −CO2CH3,(CH2)2OH,−CH2NH(CH3), −C(CH3)2OHおよび−CH2N(CH3)2からなる群から独立に選ばれる 、請求項3記載の方法。 5. Rが、アミン、アミド、スルホキシド、スルホネート、ヒドロキシル、グ アニジニウム、ポリアミン、プトラセン、またはスペルマジンからなる群から選 ばれる極性官能基をも含む、請求項1記載の方法。 6. Lが、アミン、スルホネート、ヒドロキシル、グアニジニウム、ポリアミ ン、プトラセン、またはスペルマジンからなる群から選ばれる1個以上の官能基 (R3)で置換されている、請求項1記載の方法。 7. 前記2個の2電子π−配位子が、エチレン類、プロペン類、ブテン類、ペ ンテン類、シクロペンテン類、ヘキセン類およびシクロヘキセン類からなる群か ら独立に選ばれる、請求項1記載の方法。 8. 前記4電子π−配位子が、シクロブタジエン、シクロヘキサジエン、また はシクロオクタジエンからなる群から選ばれる、請求項1記載の方法。 9. 前記水溶液が有機溶媒の水中20%から100%の混合物を含み、その有 機溶媒が、アルキルアルコール、N,N−ジメチルホルムアミド、テトラヒドロ フラン、またはジオキサンからなる群から選ばれる、請求項1記載の方法。 10.前記アルキルアルコールが、メタノールまたはエタノールからなる群から 選ばれる、請求項9記載の方法。 11.前記水溶液が、前記有機溶媒の水中20%から40%の混合物を含む、請 求項9記載の方法。 12. 一般式 Rx−C−M−L 〔式中、Cはシクロペンタジエニルまたはインデニル基を表し; Rはニトリル、エステル、ケトン、アミド、クロロ、またはフルオロからなる 群から選ばれる電子求引基であり; X=0,1または2; MはCo,RhまたはIrからなる群から選ばれる遷移金属であり; Lは遷移金属の2個の別個の2電子π−配位子または1個の4電子π−配位子 からなる群から選ばれる配位子である〕 を有する水溶性遷移金属触媒。 13.Rが、アミン、アミド、スルホキシド、スルホネート、ヒドロキシル、グ アニジニウム、ポリアミン、プトラセン、またはスペルマジンからなる群から選 ばれる極性官能基をも含む、請求項12記載の水溶性遷移金属触媒。 14.Lが、アミン、スルホネート、ヒドロキシル、グアニジニウム、ポリアミ ン、プトラセン、またはスペルマジンからなる群から選ばれる1個以上の官能基 (R1)を含む、請求項13記載の水溶性遷移金属触媒。 15.一般式: 〔式中、Rはニトリル、エステル、ケトン、アミド、クロロまたはフルオロか らなる群から選ばれる電子求引基であり;MはCo,RhまたはIrからなる群 から選ばれる遷移金属である〕 を有する水溶性遷移金属触媒。 16.一般式: 〔式中、Rはニトリル、エステル、ケトン、アミド、クロロまたはフルオロか らなる群から選ばれる電子求引基であり;MはCo,RhまたはIrからなる群 から選ばれる遷移金属であり;R3はアミン、スルホネート、ヒドロキシル、グ アニジニウム、ポリアミン、プトラセン、またはスペルマジンからなる群から選 ばれる極性官能基である〕 を有する水溶性遷移金属触媒。 17.一般式: 〔式中、Rはニトリル、エステル、ケトン、アミド、クロロまたはフルオロか らなる群から選ばれる電子求引基であり;MはCo,RhまたはIrからなる群 から選ばれる遷移金属であり;R3はアミン、スルホネート、ヒドロキシル、グ アニジニウム、ポリアミン、プトラセン、またはスペルマジンからなる群から選 ばれる極性官能基であり;n=1〜8である〕 を有する水溶性遷移金属触媒。 18.式: を有する水溶性遷移金属触媒。 19.式: を有する水溶性遷移金属触媒。 20.一般式: 〔式中,R1はHまたは−CH2OHからなる群から選ばれ、R2は −CH2OH,−COCH3,−CO2CH3,(CH2)2OH, −CH2NH(CH3),−C(CH3)2OHまたは−CH2N(CH3)2 からなる群から選ばれる〕 を有する、置換芳香族化合物。 21.一般式: 〔式中,R1はHまたは−CH2OHからなる群から選ばれ、R2は −CH2OH,−COCH3,−CO2CH3,(CH2)2OH, −CH2NH(CH3),−C(CH3)2OHまたは−CH2N(CH3)2 からなる群から選ばれる〕 を有する置換芳香族化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/619,228 US5659069A (en) | 1996-03-20 | 1996-03-20 | Method for the cyclotrimerization of alkynes in aqueous solutions |
US08/619,228 | 1996-03-20 | ||
PCT/US1997/002820 WO1997034857A1 (en) | 1996-03-20 | 1997-02-25 | Method for the cyclotrimerization of alkynes in aqueous solutions |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007154908A Division JP2007277256A (ja) | 1996-03-20 | 2007-06-12 | 水溶液中でのアルキンの環状三量化法 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2000506888A true JP2000506888A (ja) | 2000-06-06 |
Family
ID=24481004
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9533471A Pending JP2000506888A (ja) | 1996-03-20 | 1997-02-25 | 水溶液中でのアルキンの環状三量化法 |
JP2007154908A Pending JP2007277256A (ja) | 1996-03-20 | 2007-06-12 | 水溶液中でのアルキンの環状三量化法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007154908A Pending JP2007277256A (ja) | 1996-03-20 | 2007-06-12 | 水溶液中でのアルキンの環状三量化法 |
Country Status (11)
Country | Link |
---|---|
US (3) | US5659069A (ja) |
EP (1) | EP0888268B1 (ja) |
JP (2) | JP2000506888A (ja) |
AT (1) | ATE226929T1 (ja) |
AU (1) | AU715066B2 (ja) |
CA (1) | CA2248352C (ja) |
DE (1) | DE69716720T2 (ja) |
DK (1) | DK0888268T3 (ja) |
ES (1) | ES2185912T3 (ja) |
PT (1) | PT888268E (ja) |
WO (1) | WO1997034857A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010530015A (ja) * | 2007-06-11 | 2010-09-02 | ザ ホン コン ユニバーシティ オブ サイエンス アンド テクノロジイ | アルキンのメタルフリー環状三量化による、アシルアリレンおよびハイパーブランチポリアシルアリレンの合成 |
JP2012533612A (ja) * | 2009-07-23 | 2012-12-27 | サントゥル ナシオナル ドゥ ラ ルシェルシュ シアンティ フィック セーエヌエールエス | セレノキノン由来の活性有機金属錯体、該錯体の製造方法、および、該錯体の用途 |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003051314A2 (en) * | 2001-12-18 | 2003-06-26 | Medallion Biomedical, Llc | Antibiotic compounds |
WO2004013159A2 (en) * | 2002-08-05 | 2004-02-12 | Cropsolution, Inc. | RECOMBINANT BIOTIN CARBOXYLASE DOMAINS FOR IDENTIFICATION OF ACETYL CoA CARBOXYLASE INHIBITORS |
US8143465B2 (en) * | 2005-05-02 | 2012-03-27 | The Hong Kong University Of Science & Technology | Soluble branched triaroylbenzene-based polymer and its synthetic method |
US9434663B2 (en) | 2012-08-21 | 2016-09-06 | Uop Llc | Glycols removal and methane conversion process using a supersonic flow reactor |
US8927769B2 (en) | 2012-08-21 | 2015-01-06 | Uop Llc | Production of acrylic acid from a methane conversion process |
US9689615B2 (en) | 2012-08-21 | 2017-06-27 | Uop Llc | Steady state high temperature reactor |
US8937186B2 (en) | 2012-08-21 | 2015-01-20 | Uop Llc | Acids removal and methane conversion process using a supersonic flow reactor |
US9707530B2 (en) | 2012-08-21 | 2017-07-18 | Uop Llc | Methane conversion apparatus and process using a supersonic flow reactor |
US9656229B2 (en) | 2012-08-21 | 2017-05-23 | Uop Llc | Methane conversion apparatus and process using a supersonic flow reactor |
US9327265B2 (en) | 2012-08-21 | 2016-05-03 | Uop Llc | Production of aromatics from a methane conversion process |
US8933275B2 (en) | 2012-08-21 | 2015-01-13 | Uop Llc | Production of oxygenates from a methane conversion process |
US9205398B2 (en) | 2012-08-21 | 2015-12-08 | Uop Llc | Production of butanediol from a methane conversion process |
US9023255B2 (en) | 2012-08-21 | 2015-05-05 | Uop Llc | Production of nitrogen compounds from a methane conversion process |
US9308513B2 (en) | 2012-08-21 | 2016-04-12 | Uop Llc | Production of vinyl chloride from a methane conversion process |
US9370757B2 (en) | 2012-08-21 | 2016-06-21 | Uop Llc | Pyrolytic reactor |
CN110041455B (zh) * | 2019-05-21 | 2021-06-25 | 南京工业大学 | 一种炔烃聚合的方法 |
Family Cites Families (9)
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US2613208A (en) * | 1949-06-29 | 1952-10-07 | Rohm & Haas | Tertiary aminomethylbenzenes |
US2542417A (en) * | 1949-12-10 | 1951-02-20 | Gen Aniline & Film Corp | Hexamethyl benzene compounds |
BE567744A (ja) * | 1957-05-16 | |||
DE1159951B (de) * | 1961-10-21 | 1963-12-27 | Basf Ag | Verfahren zur katalytischen Trimerisierung von Acetylenverbindungen |
DE2103678A1 (ja) * | 1971-01-27 | 1972-08-17 | Dynamit Nobel Ag | |
EP0110177B1 (en) * | 1982-11-06 | 1989-03-22 | Denki Kagaku Kogyo Kabushiki Kaisha | Substituted cyclopentadienyl cobalt complexes and synthesis of pyridine homologues by means of the complexes |
DE3819487A1 (de) * | 1988-06-08 | 1989-12-14 | Basf Ag | Uebergangsmetallkomplexe |
DE4205115C1 (ja) * | 1992-02-20 | 1993-08-26 | Huels Ag, 4370 Marl, De | |
US5194538A (en) * | 1992-07-15 | 1993-03-16 | Polysar Corporation | Preparation of butyl rubber with bimodal molecular weight distribution |
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1996
- 1996-03-20 US US08/619,228 patent/US5659069A/en not_active Expired - Lifetime
-
1997
- 1997-02-25 AU AU21351/97A patent/AU715066B2/en not_active Ceased
- 1997-02-25 ES ES97906737T patent/ES2185912T3/es not_active Expired - Lifetime
- 1997-02-25 DE DE69716720T patent/DE69716720T2/de not_active Expired - Lifetime
- 1997-02-25 CA CA002248352A patent/CA2248352C/en not_active Expired - Fee Related
- 1997-02-25 JP JP9533471A patent/JP2000506888A/ja active Pending
- 1997-02-25 AT AT97906737T patent/ATE226929T1/de not_active IP Right Cessation
- 1997-02-25 DK DK97906737T patent/DK0888268T3/da active
- 1997-02-25 PT PT97906737T patent/PT888268E/pt unknown
- 1997-02-25 EP EP97906737A patent/EP0888268B1/en not_active Expired - Lifetime
- 1997-02-25 WO PCT/US1997/002820 patent/WO1997034857A1/en active IP Right Grant
- 1997-03-13 US US08/816,588 patent/US5760266A/en not_active Expired - Lifetime
- 1997-03-13 US US08/816,709 patent/US6225500B1/en not_active Expired - Fee Related
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2007
- 2007-06-12 JP JP2007154908A patent/JP2007277256A/ja active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010530015A (ja) * | 2007-06-11 | 2010-09-02 | ザ ホン コン ユニバーシティ オブ サイエンス アンド テクノロジイ | アルキンのメタルフリー環状三量化による、アシルアリレンおよびハイパーブランチポリアシルアリレンの合成 |
KR101521964B1 (ko) * | 2007-06-11 | 2015-05-20 | 더 홍콩 유니버시티 오브 사이언스 앤드 테크놀러지 | 알킨의 무금속 삼합체고리화에 의한 아실아릴렌 및 하이퍼브랜치형 폴리(아실아릴렌)의 합성 |
JP2012533612A (ja) * | 2009-07-23 | 2012-12-27 | サントゥル ナシオナル ドゥ ラ ルシェルシュ シアンティ フィック セーエヌエールエス | セレノキノン由来の活性有機金属錯体、該錯体の製造方法、および、該錯体の用途 |
Also Published As
Publication number | Publication date |
---|---|
AU715066B2 (en) | 2000-01-13 |
US5760266A (en) | 1998-06-02 |
WO1997034857A1 (en) | 1997-09-25 |
DE69716720T2 (de) | 2003-06-12 |
DE69716720D1 (de) | 2002-12-05 |
DK0888268T3 (da) | 2003-03-03 |
EP0888268A1 (en) | 1999-01-07 |
EP0888268B1 (en) | 2002-10-30 |
CA2248352A1 (en) | 1997-09-25 |
ES2185912T3 (es) | 2003-05-01 |
CA2248352C (en) | 2008-04-15 |
AU2135197A (en) | 1997-10-10 |
ATE226929T1 (de) | 2002-11-15 |
EP0888268A4 (en) | 1999-06-09 |
PT888268E (pt) | 2003-03-31 |
JP2007277256A (ja) | 2007-10-25 |
US6225500B1 (en) | 2001-05-01 |
US5659069A (en) | 1997-08-19 |
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