High metathesis activity ruthenium and osmium metal carbene comp

Organic compounds -- part of the class 532-570 series – Organic compounds – Heavy metal containing

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

556136, 556137, 502152, 502162, C07F 1500, C07F 950

Patent

active

06111121&

ABSTRACT:
Ruthenium and osmium carbene compounds that are stable in the presence of a variety of functional groups and can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins are disclosed. Also disclosed are methods of making the carbene compounds. The carbene compounds are of the formula ##STR1## where M is Os or Ru; R.sup.1 is hydrogen; R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; X and X.sup.1 are independently selected from any anionic ligand; and L and L.sup.1 are independently selected from any neutral electron donor. The ruthenium and osmium carbene compounds of the present invention may be synthesized using diazo compounds, by neutral electron donor ligand exchange, by cross metathesis, using acetylene, using cumulated olefins, and in a one-pot method using diazo compounds and neutral electron donors. The ruthenium and osmium carbene compounds of the present invention may be used to catalyze olefin metathesis reactions including, but not limited to, ROMP, RCM, depolymerization of unsaturated polymers, synthesis of telechelic polymers, and olefin synthesis.

REFERENCES:
patent: 4883851 (1989-11-01), Grubbs et al.
patent: 4945135 (1990-07-01), Grubbs et al.
patent: 4945144 (1990-07-01), Grubbs et al.
patent: 5198511 (1993-03-01), Brown-Wensley et al.
patent: 5296566 (1994-03-01), Brown-Wensley et al.
patent: 5312940 (1994-05-01), Grubbs et al.
patent: 5342909 (1994-08-01), Grubbs et al.
Burrell et al., "Synthesis and Reactions of Ru(=CH.sub.2)CI(NO)PPh.sub.3).sub.2, A Stable Terminal Methylene Complex and the Crystal Structure of Ru(CH.sub.2 PPh.sub.3)(n.sup.2 -C.sub.2 F.sub.4)CI(NO)(PPh.sub.3)", J. Chem. Soc., Dalton Trans., 609-614, (1991).
Ivin, K.J. "Olefin Metathesis", Academic Press, vii-x and 34-36, (1983).
McGrath et al., "Aqueous Ring-opening Metathesis Polymerization of 7-Oxanorbornene Derivatives Using Ruthenium Catalysts", Kluwer Academic Publishers, 525-536, (1990).
Novak et al., "Catalytic Organometallic Chemistry in Water: The Aqueous Ring-Opening Metathesis Polymerization of 7-Oxanorbornene Derivatives Using Ruthenium Catalysts", JACS, vol. 110, 7542-7543, (1988).
Hillmeyer et al., "The Aqueous Ring-Opening Metathesis Polymerization of Exo-N-methyl-7-oxabicyclo [2.2.1] hept-5-ene-2, 3-dicarbonximide", Polymer Preprints, vol. 32, pp. 162-163, (1991).
Carter et al., "Review of the Chemistry of Cyclopropane Compounds", Chemical Reviews, vol. 64, No. 5, 497-525, (1964).
Schmidbauer et al., "Ylide Chemistry: An Account of Structural, Conformational and Redox Investigations", Phosphorus and Sulfur, vol. 18, pp. 167-170 (1983).
"Metathesis of Functionalized Olefin", J. of Molecules Catalysis, vol. 15, 35-45 (1982).
Bruce et al., "Cyclopentadienyl-Ruthenium and -Osmium Chemistry. Some Reactions of Substituted Vinylidene Complexes", J. of Organometallic Chemistry, vol. 171, C5-C8 (1979).
Green et al., "Carbene Complexes of Iron, Molybdenum, and Ruthenium: A New Route to Metal-Carbene Derivatives", J. Chem. Soc. (A), 794-797, (1971).
Bozec et al., "A New Route to Vinylcarbene Metal Complexes on One Step from 2-Propyn-1-ols and Arene Ruthenium(II) Derivatives", J. Chem. Soc., Chem. Commun., 219-221, (1989).
Grundy et al., "Migratory-Insertion Reactions of Osmium(II) Ethyl Complexes Derived from an Osmium(0) Ethylene Complex", J. of Organometallic Chemistry, vol. 216, 255-262, (1981).
Grundy et al., "Propionyl Complexes of Ruthenium Derived from the Reaction of Ethylene with RuHCI(CO).sub.2 (PPh.sub.3).sub.2 ", J. Organometallic Chemistry, vol. 265, 77-85, (1984).
Schrock, R.R., "Living Ring-opening Metathesis Polymerization Catalyzed by well-characterized Transition-metal Alkylidene Complexes", Acc. Chem. Res., vol. 23, 158-165, (1990).
Fu et al., "Catalytic Ring-closing Metathesis of Functionalized Dienes by a Ruthenium Carbene Complex", J. of the Am. Chem. Soc., vol. 115, No. 21, 9856-9857, (1993).
Grubbs et al., "Ring-opening Metathesis Polymerization Catalysts" Polymer Preprints, vol. 34, No. 2, 688.
Hillmeyer et al., "The ROMP of COD by a Well-defined Metathesis Catalyst in the Presence of a Disfunctional Chain Transfer Agent: The Preparation of Hydroxy-telechelic 1,4-Poly(butadiene)", Polymer Preprints, vol. 34, No. 2, 388-389.
Hillmeyer et al., "Preparation of Hydroxy-telechelic Poly(butadiene) via Ring-opening Metathesis Polymerization Employing a Well-defined Metathesis Catalyst", Macromolecules, vol. 26, No. 4, 872-874, (1993).
Nguyen et al. "Syntheses and Activities of New Single-component, Ruthenium-based Olefin Metathesis Catalysts", J. Am. Chem. Soc., vol. 115, No. 21, 9858-9859, (1993).
Nguyen et al., "Ring-opening Metathesis Polymerization (ROMP) of Norbornene by a Group VIII Carbene Complex in Protic Media", J. Am. Chem. Soc., vol. 114, 3974-3975 (1992).
Eine Reihe definierter Metathesekatalysatoren -Synthese von und Reaktionen mit [RuCI.sub.2 (=CHR')(PR.sub.3).sub.2 ], Angew. Chem., vol. 107, No. 18, 2179-2181, (1995).
Fraser et al., "Degradeable Cyclooctadiene/acetal Copolymers: Useful Precursors to 1,4-Hydroxytelechelic Polybutadiene", Chicago Book of Abstracts, 210th ACS Meeting, No. 091, (1995).
Fraser et al., "Degradeable Clooctadiene/acetal Copolymers: Precursors to 1,4-Hydroxytelechelic Polybutadiene", Polymer Preprints, vol. 36, No. 2, 237-238 (1995).
Fraser et al., "Degradeable Cyclooctadiene/acetal Copolymers: Versatile Precursors to 1,4-Hydroxytelechelic Polybutadiene and Hydroxytelechelic Polyethylene", Macromolecules, vol. 28, No. 21, 1256-1261, (1995).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

High metathesis activity ruthenium and osmium metal carbene comp does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with High metathesis activity ruthenium and osmium metal carbene comp, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and High metathesis activity ruthenium and osmium metal carbene comp will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1251479

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.