CA2413852C - Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis - Google Patents

Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis Download PDF

Info

Publication number
CA2413852C
CA2413852C CA2413852A CA2413852A CA2413852C CA 2413852 C CA2413852 C CA 2413852C CA 2413852 A CA2413852 A CA 2413852A CA 2413852 A CA2413852 A CA 2413852A CA 2413852 C CA2413852 C CA 2413852C
Authority
CA
Canada
Prior art keywords
group
aryl
alkyl
olefin
substituted
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 - Fee Related
Application number
CA2413852A
Other languages
English (en)
French (fr)
Other versions
CA2413852A1 (en
Inventor
Robert H. Grubbs
Arnab K. Chatterjee
John P. Morgan
Matthias Scholl
Tae-Lim Choi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
California Institute of Technology
Original Assignee
California Institute of Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by California Institute of Technology filed Critical California Institute of Technology
Publication of CA2413852A1 publication Critical patent/CA2413852A1/en
Application granted granted Critical
Publication of CA2413852C publication Critical patent/CA2413852C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • 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
    • C07C45/673—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 change of size of the carbon skeleton
    • 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
    • C07C45/69—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 addition to carbon-to-carbon double or triple bonds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings 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
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C07D321/02—Seven-membered rings
    • C07D321/04—Seven-membered rings not condensed with other rings
    • C07D321/08—1,4-Dioxepines; Hydrogenated 1,4-dioxepines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
CA2413852A 2000-06-23 2001-06-25 Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis Expired - Fee Related CA2413852C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US21375700P 2000-06-23 2000-06-23
US60/213,757 2000-06-23
PCT/US2001/020180 WO2002000590A1 (en) 2000-06-23 2001-06-25 Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis

Publications (2)

Publication Number Publication Date
CA2413852A1 CA2413852A1 (en) 2002-01-03
CA2413852C true CA2413852C (en) 2012-06-05

Family

ID=22796381

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2413852A Expired - Fee Related CA2413852C (en) 2000-06-23 2001-06-25 Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis

Country Status (8)

Country Link
US (1) US6794534B2 (enExample)
EP (1) EP1301458B1 (enExample)
JP (2) JP2004510699A (enExample)
AU (3) AU7143001A (enExample)
CA (1) CA2413852C (enExample)
IL (2) IL153578A0 (enExample)
WO (1) WO2002000590A1 (enExample)
ZA (1) ZA200300207B (enExample)

Families Citing this family (93)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU767185B2 (en) * 1998-03-23 2003-11-06 President And Fellows Of Harvard College Synthesis of compounds and libraries of compounds
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
ATE409215T1 (de) 1998-05-05 2008-10-15 Massachusetts Inst Technology Emittierende polymere und vorrichtungen diese polymere enthaltend
US20050147534A1 (en) 1998-05-05 2005-07-07 Massachusetts Institute Of Technology Emissive sensors and devices incorporating these sensors
US7329758B1 (en) * 1999-05-24 2008-02-12 California Institute Of Technology Imidazolidine-based metal carbene metathesis catalysts
EP1373170A4 (en) * 2001-03-30 2007-03-21 California Inst Of Techn CROSS-METATHESIS REACTION OF FUNCTIONALIZED AND SUBSTITUTED OLEFINS USING GROUP 8 METAL TRANSITION CARBENE COMPLEXES AS METATHESIS CATALYSTS
CN1265882C (zh) 2001-08-01 2006-07-26 加州理工学院 六配位钌或锇金属卡宾易位催化剂
WO2003093351A1 (en) * 2002-05-06 2003-11-13 Kerr Corporation Composition curable by metathesis reaction
EP1371689A1 (en) * 2002-06-14 2003-12-17 Dainippon Ink And Chemicals, Inc. Storage stable curable coating compositions
AU2003258013A1 (en) * 2002-08-01 2004-02-23 California Institute Of Technology Synthesis of macrocyclic polymers by ring insertion polymerization of cyclic olefin monomers
US7002049B2 (en) * 2002-08-19 2006-02-21 Eastman Chemical Company Process for α,β-dihydroxyalkenes and derivatives
US6737531B1 (en) 2002-12-17 2004-05-18 Brookhaven Science Associates, Llc Catalysts for hydrogenation and hydrosilylation, methods of making and using the same
CN1802341A (zh) * 2003-01-13 2006-07-12 卡吉尔公司 制备工业化学品的方法
US7683148B2 (en) * 2003-05-06 2010-03-23 Kerr Corporation Metathesis-curable composition with a reaction control agent
US7060769B2 (en) * 2003-05-06 2006-06-13 Kerr Corporation Method of curing composition by metathesis reaction using reaction control agent
US7060770B2 (en) * 2003-05-06 2006-06-13 Kerr Corporation Metathesis-curable composition with a reaction control agent
US7173097B2 (en) 2003-05-06 2007-02-06 Kerr Corporation Metathesis-curable composition with a reaction control agent
DE602004014958D1 (de) * 2003-10-09 2008-08-21 Dow Global Technologies Inc Verbessertes verfahren zur synthese ungesättigter alkohole
WO2006034081A2 (en) 2004-09-17 2006-03-30 Massachusetts Institute Of Technology Polymers for analyte detection
US7001590B1 (en) 2004-11-15 2006-02-21 Kerr Corporation Metathesis-curable composition
US7625551B2 (en) * 2004-11-15 2009-12-01 Kerr Corporation Polyether-based dental impression material curable by metathesis reaction
US7645443B2 (en) * 2004-11-15 2010-01-12 Kerr Corporation Polyether-based composition curable by metathesis reaction
US7078362B2 (en) * 2004-12-09 2006-07-18 Equistar Chemicals, Lp Carbene donor-modified Ziegler-Natta catalysts
US8101697B2 (en) * 2005-02-01 2012-01-24 Bridgestone Corporation Multi-functionalized high-trans elastomeric polymers
WO2007081987A2 (en) * 2006-01-10 2007-07-19 Elevance Renewable Sciences, Inc. Method of making hydrogenated metathesis products
WO2007092633A2 (en) * 2006-02-09 2007-08-16 Elevance Renewable Sciences, Inc. Antimicrobial compositions, methods and systems
US7951232B2 (en) * 2006-02-09 2011-05-31 Elevance Renewable Sciences, Inc. Surface coating compositions and methods
EP1847245A1 (en) * 2006-02-21 2007-10-24 Kerr Corporation Method for making alkoxy-siloxane polyether carboxylates terminated with functional olefin groups
DE102006008521A1 (de) * 2006-02-22 2007-08-23 Lanxess Deutschland Gmbh Verwendung von Katalysatoren mit erhöhter Aktivität für die NBR-Metathese
JP4613853B2 (ja) 2006-03-01 2011-01-19 トヨタ自動車株式会社 複数金属錯体含有化合物及び金属錯体
JP2009529092A (ja) 2006-03-07 2009-08-13 エレバンス リニューアブル サイエンシーズ， インク． 不飽和ポリオールエステルメタセシス反応生成物類を含む組成物
JP5361715B2 (ja) 2006-07-12 2013-12-04 エレバンス リニューアブル サイエンシーズ， インク． 環状オレフィンと種子油および類似物との開環交差メタセシス反応
WO2008010961A2 (en) 2006-07-13 2008-01-24 Elevance Renewable Sciences, Inc. Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis
US8283423B2 (en) * 2006-09-29 2012-10-09 Massachusetts Institute Of Technology Polymer synthetic technique
US8802447B2 (en) 2006-10-05 2014-08-12 Massachusetts Institute Of Technology Emissive compositions with internal standard and related techniques
EP2076483A4 (en) 2006-10-13 2013-12-04 Elevance Renewable Sciences METHODS FOR PRODUCING ORGANIC COMPOUNDS BY METATHESIS AND HYDROCYANATION
WO2008140468A2 (en) * 2006-10-13 2008-11-20 Elevance Renewable Sciences, Inc. METHODS OF MAKING α, ω -DICARBOXYLIC ACID ALKENE DERIVATIVES BY METATHESIS
WO2008046106A2 (en) 2006-10-13 2008-04-17 Elevance Renewable Sciences, Inc. Synthesis of terminal alkenes from internal alkenes via olefin metathesis
US20090215189A1 (en) 2006-10-27 2009-08-27 Massachusetts Institute Of Technology Sensor of species including toxins and chemical warfare agents
RU2320640C1 (ru) * 2006-12-27 2008-03-27 ООО "Объединенный центр исследований и разработок" СПОСОБ ПОЛУЧЕНИЯ ЭФИРОВ α,β-НЕНАСЫЩЕННЫХ ЖИРНЫХ КИСЛОТ
US9284515B2 (en) 2007-08-09 2016-03-15 Elevance Renewable Sciences, Inc. Thermal methods for treating a metathesis feedstock
US8283419B2 (en) 2008-06-20 2012-10-09 Exxonmobil Chemical Patents Inc. Olefin functionalization by metathesis reaction
US8283428B2 (en) * 2008-06-20 2012-10-09 Exxonmobil Chemical Patents Inc. Polymacromonomer and process for production thereof
US8399725B2 (en) 2008-06-20 2013-03-19 Exxonmobil Chemical Patents Inc. Functionalized high vinyl terminated propylene based oligomers
US8802797B2 (en) 2008-06-20 2014-08-12 Exxonmobil Chemical Patents Inc. Vinyl-terminated macromonomer oligomerization
US8372930B2 (en) * 2008-06-20 2013-02-12 Exxonmobil Chemical Patents Inc. High vinyl terminated propylene based oligomers
JP5591238B2 (ja) 2008-08-26 2014-09-17 ビーエーエスエフ ソシエタス・ヨーロピア 冷メントール受容体ｔｒｐｍ８の低分子量モジュレーターの検出および使用
FR2938533B1 (fr) * 2008-11-17 2010-11-19 Arkema France Procede de synthese d'un omega-aminoacide ou ester a partir d'un acide ou ester gras mono-insature
FR2941694B1 (fr) * 2009-02-05 2011-02-11 Arkema France Procede de synthese d'un omega-aminoacide ou ester a partir d'un acide ou ester gras mono-insature.
DE102010002558A1 (de) * 2009-11-20 2011-06-01 Symrise Ag Verwendung physiologischer Kühlwirkstoffe und Mittel enthaltend solche Wirkstoffe
BR112012029589B1 (pt) 2010-05-22 2021-01-19 Stepan Company processo para recuperação de petróleo de uma formação contendo petróleo
US8846587B2 (en) 2011-03-24 2014-09-30 Elevance Renewable Sciences, Inc. Functionalized monomers and polymers
US8399724B2 (en) 2011-03-25 2013-03-19 Exxonmobil Chemical Patents Inc. Vinyl terminated higher olefin copolymers and methods to produce thereof
US8426659B2 (en) 2011-03-25 2013-04-23 Exxonmobil Chemical Patents Inc. Vinyl terminated higher olefin polymers and methods to produce thereof
US8669330B2 (en) 2011-03-25 2014-03-11 Exxonmobil Chemical Patents Inc. Olefin triblock polymers via ring-opening metathesis polymerization
US8501894B2 (en) 2011-03-25 2013-08-06 Exxonmobil Chemical Patents Inc. Hydrosilyation of vinyl macromers with metallocenes
US8940839B2 (en) 2011-03-25 2015-01-27 Exxonmobil Chemical Patents Inc. Diblock copolymers prepared by cross metathesis
US8623974B2 (en) 2011-03-25 2014-01-07 Exxonmobil Chemical Patents Inc. Branched vinyl terminated polymers and methods for production thereof
US8455597B2 (en) 2011-03-25 2013-06-04 Exxonmobil Chemical Patents Inc. Catalysts and methods of use thereof to produce vinyl terminated polymers
US8835563B2 (en) 2011-03-25 2014-09-16 Exxonmobil Chemical Patents Inc. Block copolymers from silylated vinyl terminated macromers
US8841397B2 (en) 2011-03-25 2014-09-23 Exxonmobil Chemical Patents Inc. Vinyl terminated higher olefin polymers and methods to produce thereof
US8669326B2 (en) 2011-03-25 2014-03-11 Exxonmobil Chemical Patents Inc. Amine functionalized polyolefin and methods for preparation thereof
US8785562B2 (en) 2011-03-25 2014-07-22 Exxonmobil Chemical Patents Inc. Amphiphilic block polymers prepared by alkene metathesis
US9315748B2 (en) 2011-04-07 2016-04-19 Elevance Renewable Sciences, Inc. Cold flow additives
US8604148B2 (en) 2011-11-29 2013-12-10 Exxonmobil Chemical Patents Inc. Functionalization of vinyl terminated polymers by ring opening cross metathesis
US9012385B2 (en) 2012-02-29 2015-04-21 Elevance Renewable Sciences, Inc. Terpene derived compounds
US8796376B2 (en) 2012-03-26 2014-08-05 Exxonmobil Chemical Patents Inc. Functionalized polymers and oligomers
MY169208A (en) 2012-04-24 2019-03-18 Stepan Co Unsaturated fatty alcohol alkoxylates from natural oil metathesis
US20130281688A1 (en) 2012-04-24 2013-10-24 Elevance Renewable Sciences, Inc Unsaturated fatty alcohol compositions and derivatives from natural oil metathesis
EP2841541B1 (en) 2012-04-24 2020-11-11 Stepan Company Unsaturated fatty alcohol derivatives from natural oil metathesis
US9890348B2 (en) 2012-06-20 2018-02-13 Elevance Renewable Sciences, Inc. Natural oil metathesis compositions and methods
US9266918B2 (en) 2013-03-14 2016-02-23 Elevance Renewable Sciences, Inc. Alkenyl glycosides and their preparation
CN105189708A (zh) 2013-03-14 2015-12-23 埃莱万斯可再生能源科学股份有限公司 用金属醇盐处理易位原料的方法
EP2976321A1 (en) 2013-03-20 2016-01-27 Elevance Renewable Sciences, Inc. Acid catalyzed oligomerization of alkyl esters and carboxylic acids
US10000601B2 (en) 2014-03-27 2018-06-19 Trent University Metathesized triacylglycerol polyols for use in polyurethane applications and their related properties
WO2015143562A1 (en) 2014-03-27 2015-10-01 Trent University Metathesized triacylglycerol green polyols from palm oil for use in polyurethane applications and their related physical properties
WO2015143563A1 (en) 2014-03-27 2015-10-01 Trent University Certain metathesized natural oil triacylglycerol polyols for use in polyurethane applications and their related physical properties
FR3024450B1 (fr) * 2014-08-01 2018-01-26 Arkema France Synthese d'un compose insature a ramification cyclique par metathese croisee
US9777245B2 (en) 2015-01-30 2017-10-03 Trent University Methods of fractionating metathesized triacylglycerol polyols and uses thereof
WO2016129600A1 (ja) * 2015-02-09 2016-08-18 旭硝子株式会社 含フッ素重合体の製造方法
WO2016140201A1 (ja) * 2015-03-03 2016-09-09 旭硝子株式会社 フッ素原子と炭素－炭素二重結合とを含む有機基が導入された基材の製造方法
JP2016160235A (ja) * 2015-03-03 2016-09-05 旭硝子株式会社 オクタフルオロペンテンの製造方法
JP2016160231A (ja) * 2015-03-03 2016-09-05 旭硝子株式会社 含フッ素オレフィンの製造方法
JP2016160230A (ja) * 2015-03-03 2016-09-05 旭硝子株式会社 含フッ素オレフィンの製造方法
JP6384363B2 (ja) * 2015-03-03 2018-09-05 Ａｇｃ株式会社 含フッ素オレフィンの製造方法
JP2016160234A (ja) * 2015-03-03 2016-09-05 旭硝子株式会社 ヘキサフルオロブテンの製造方法
EP3124579A1 (en) 2015-07-31 2017-02-01 Total Marketing Services Lubricant composition comprising branched diesters and viscosity index improver
EP3124580A1 (en) 2015-07-31 2017-02-01 Total Marketing Services Branched diesters for use to reduce the fuel consumption of an engine
EP3503999B1 (en) * 2016-08-24 2022-12-07 Umicore Ag & Co. Kg Synthesis and characterization of metathesis catalysts
JP6673107B2 (ja) * 2016-09-07 2020-03-25 Ａｇｃ株式会社 フッ素原子を含む有機基が導入された基材の製造方法
WO2018159641A1 (ja) * 2017-03-02 2018-09-07 Ａｇｃ株式会社 含フッ素シラン化合物の製造方法及び含フッ素シラン化合物
EP3675809B1 (de) 2017-08-31 2023-09-27 Basf Se Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe
CN113272267A (zh) 2018-12-10 2021-08-17 普罗维维公司 共轭二烯信息素及相关化合物的合成

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5312940A (en) 1992-04-03 1994-05-17 California Institute Of Technology Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
EP0773948A4 (en) * 1992-04-03 1998-09-02 California Inst Of Techn HIGHLY ACTIVE RUTHENIUM OR OSMIUM METAL CARBEN COMPLEXES FOR OLEFIN METHETHESE REACTIONS AND THEIR SYNTHESIS
US5710298A (en) 1992-04-03 1998-01-20 California Institute Of Technology Method of preparing ruthenium and osmium carbene complexes
US5811515A (en) 1995-06-12 1998-09-22 California Institute Of Technology Synthesis of conformationally restricted amino acids, peptides, and peptidomimetics by catalytic ring closing metathesis
US5728785A (en) 1995-07-07 1998-03-17 California Institute Of Technology Romp polymerization in the presence of peroxide crosslinking agents to form high-density crosslinked polymers
US5831108A (en) 1995-08-03 1998-11-03 California Institute Of Technology High metathesis activity ruthenium and osmium metal carbene complexes
DE19746040A1 (de) * 1997-10-17 1999-04-22 Basf Ag Verfahren zur Herstellung von Propen
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

Also Published As

Publication number Publication date
AU7143001A (en) 2002-01-08
IL153578A (en) 2011-10-31
JP2012229232A (ja) 2012-11-22
EP1301458B1 (en) 2015-09-09
US20020137978A1 (en) 2002-09-26
WO2002000590A1 (en) 2002-01-03
CA2413852A1 (en) 2002-01-03
EP1301458A1 (en) 2003-04-16
AU2001271430B2 (en) 2006-09-07
ZA200300207B (en) 2004-07-08
JP5779142B2 (ja) 2015-09-16
AU2010249178A1 (en) 2010-12-23
JP2004510699A (ja) 2004-04-08
IL153578A0 (en) 2003-07-06
AU2001271430C1 (en) 2002-01-08
US6794534B2 (en) 2004-09-21
EP1301458A4 (en) 2006-11-02

Similar Documents

Publication Publication Date Title
CA2413852C (en) Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis
AU2001271430A1 (en) Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis
US9403854B2 (en) Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts
CA2361148C (en) Novel methods for cross-metathesis of terminal olefins
CA2824518C (en) Z-selective olefin metathesis catalysts and their synthetic procedure
EP3164409B1 (en) Group 8 transition metal catalysts and method for making same and process for use of same in metathesis reaction
US20050203324A1 (en) Impurity reduction in Olefin metathesis reactions
US20030023123A1 (en) Impurity inhibition in olefin metathesis reactions
RU2644556C2 (ru) Каталитические комплексы с карбеновым лигандом, способ их получения и применение в реакции метатезиса
EP2838359A1 (en) Syntheses of z-olefin-containing lepidopteran insect pheromones
Shi et al. Aza‐Baylis–Hillman Reactions of N‐(Arylmethylene) diphenylphosphinamides with Activated Olefins in the Presence of Various Lewis Bases
Becht et al. Application of Rhodium Complexes of Chiral Diphenylphosphino‐Functionalized N‐Heterocyclic Carbenes as Catalysts in Enantioselective Conjugate Additions of Arylboronic Acids
Sytniczuk et al. A tunable family of CAAC-ruthenium olefin metathesis catalysts modularly derived from a large-scale produced ibuprofen intermediate
Liu et al. Rh-catalyzed highly enantioselective formation of functionalized cyclopentanes and cyclopentanones
Courchay et al. Understanding the effect of allylic methyls in olefin cross-metathesis
Lujan et al. The influence of N-heterocyclic carbene steric and electronic properties in Ru-catalysed cross metathesis reactions
Alsamarrai et al. A reaction of stabilized arsonium ylide of dicarboxylate ester with tropylium fluoroborate: An efficient strategy for ring contraction of cycloheptatriene
AU2007201132A1 (en) Synthesis of functionalized and unfuctionalized olefins via cross and ring-closing metathesis
EP1395534A1 (en) Impurity inhibition in olefin metathesis reactions
Tole et al. Synthesis and application of 1-cycloalkyl-1-(2’-pyridinyl)-methanolato ligand containing ruthenium catalysts for high temperature 1-octene metathesis
Chatterjee Investigations into the selectivity of olefin cross-metathesis using ruthenium alkylidene catalysts: Electronic and steric matching of substrates
RU2350595C1 (ru) Способ получения спиро[3.3]гептана
Brown Copper-catalyzed enantioselective conjugate additions of organometal reagents to unsaturated carbonyls: An enantioselective total synthesis of clavirolide C
JPH0840955A (ja) 環状ケトン化合物を原料とするアルデヒド類および／またはアルコール類の製造方法

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20200831