Claims
- 1. A compound of the formula
- 2. The compound of claim 1 wherein the substituent group is substituted with one or more substituted or unsubstituted groups selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, and aryl.
- 3. The compound of claim 2 wherein the substituent substitution is substituted with one or more groups selected from the group consisting of halogen, C1-C5 alkyl, C1-C5 alkoxy.
- 4. The compound of claim 1 wherein the substituent is functionalized with a moiety selected from the group consisting of hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, carboalkoxy, carbamate, and halogen.
- 5. The compound of claim 1 wherein R is hydrogen and R is selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, aryl, unsubstituted phenyl, substituted phenyl, unsubstituted vinyl, and substituted vinyl; and wherein the substituted phenyl and substituted vinyl are each independently substituted with one or more groups selected from the group consisting of C1-C5 alkyl, C1-C5 alkoxy, phenyl, hydroxyl, thiol, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, carboalkoxy, and halogen.
- 6. The compound of claim 1 wherein L is selected from the group consisting of phosphine, sulfonated phosphine, phosphite, phosphinite, phosphonite, arsine, stibine, ether, amine, amide, imine, sulfoxide, carboxyl, nitrosyl, pyridine, and thioether.
- 7. The compound of claim 6 wherein L is a phosphine of the formula PR3R4R5 wherein R3, R4, and R5 are each independently selected from the group consisting of aryl and C1-C10 alkyl.
- 8. The compound of claim 7 wherein R3, R4, and R5 are each independently selected from the group consisting of primary alkyl, secondary alkyl, and cycloalkyl.
- 9. The compound of claim 7 wherein L is selected from the group consisting of P(cyclohexyl)3, P(cyclopentyl)3, P(isopropyl)3, and P(phenyl)3.
- 10. The compound of claim 1 wherein X and X1 are each independently selected from the group consisting of hydrogen, halogen, substituted moiety and unsubstituted moiety, wherein the moiety is selected from the group consisting of C1-C20 alkyl, aryl, C1-C20 alkoxide, aryloxide, C3-C20 alkyldiketonate, aryldiketonate, C1-C20 carboxylate, arylsulfonate, C1-C20 alkylsulfonate, C1-C20 alkylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl, and wherein the moiety substitution is selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, and aryl.
- 11. The compound of claim 1 wherein X and X1 are each independently selected from the group consisting of halide, benzoate, C1-C5 carboxylate, C1-C5 alkyl, phenoxy, C1-C5 alkoxy, C1-C5 alkylthio, aryl, and C1-C5 alkyl sulfonate.
- 12. The compound of claim 1 wherein X and X1 are each independently selected from the group consisting of halide, CF3CO2, CH3CO2, CFH2CO2, (CH3)3CO, (CF3)2(CH3)CO, (CF3)(CH3)2CO, PhO, MeO, EtO, tosylate, mesylate, and trifluoromethanesulfonate.
- 13. The compound of claim 1 wherein R6 and R7 together form a cycloalkyl or an aryl moiety.
- 14. The compound of claim 1 wherein R6 and R7 are both hydrogen or phenyl.
- 15. The compound of claim 1 wherein R6 and R7 are the same and each is independently of the formula
- 16. The compound of claim 15 wherein R8, R9, and R10 are the same and are each methyl.
- 17. A method for synthesizing a compound of the formula
- 18. The method of claim 17 wherein the N-heterocyclic carbene ligand is triazolylidene.
- 19. The method of claim 17 wherein R6 and R7 together form a cycloalkyl or an aryl moiety.
- 20. The method of claim 17 wherein R6 and R7 are both hydrogen or phenyl.
- 21. The method of claim 17 wherein R6 and R7 are the same and each is independently of the formula
- 22. The method of claim 21 wherein R1, R9, and R10 are the same and are each methyl.
- 23. The method of claim 17 wherein W is functionalized with a functional group selected from the group consisting of hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, carboalkoxy, carbamate, and halogen.
- 24. The method of claim 17 wherein W is methoxide.
- 25. The method of claim 17 wherein X and X1 are each independently selected from the group consisting of hydrogen, halogen, substituted moiety and unsubstituted moiety, wherein the moiety is selected from the group consisting of C1-C20 alkyl, aryl, C1-C20 alkoxide, aryloxide, C3-C20 alkyldiketonate, aryldiketonate, C1-C20 carboxylate, arylsulfonate, C1-C20 alkylsulfonate, C1-C20 alkylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl, and wherein the moiety substitution is selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, and aryl;
L and L1 are each independently selected from the group consisting of phosphine, sulfonated phosphine, phosphite, phosphinite, phosphonite, arsine, stibine, ether, amine, amide, imine, sulfoxide, carboxyl, nitrosyl, pyridine, and thioether; and R is hydrogen and R1 is phenyl.
- 26. The method of claim 25 wherein X and X1 are each chloride and L and L1 are each independently selected from the group consisting of P(cyclohexyl)3, P(cyclopentyl)3, P(isopropyl)3, and P(phenyl)3.
- 27. The method of claim 17 wherein R is hydrogen, R1, R6 and R7 are each phenyl, L is PPh3, and X and X1 are each chloride.
- 28. A method for synthesizing a compound of the formula
- 29. A method for attaching a N-heterocyclic carbene ligand to a ruthenium metal carbene metathesis complex comprising:
contacting the N-heterocyclic carbene ligand with a compound of the formula 40wherein X and X1 are either the same or different and are any anionic ligand; R and R1 are either the same or different and are each independently hydrogen or a substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl, wherein each of the substituents is substituted or unsubstituted; and L and L1 are either the same or difference and are any neutral electron donor.
- 30. The method of claim 29 wherein X and X1 are each independently selected from the group consisting of hydrogen, halogen, substituted moiety and unsubstituted moiety, wherein the moiety is selected from the group consisting of C1-C20 alkyl, aryl, C1-C20 alkoxide, aryloxide, C3-C20 alkyldiketonate, aryldiketonate, C1-C20 carboxylate, arylsulfonate, C1-C20 alkylsulfonate, C1-C20 alkylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl, and wherein the moiety substitution is selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, and aryl;
L and L1 are each independently selected from the group consisting of phosphine, sulfonated phosphine, phosphite, phosphinite, phosphonite, arsine, stibine, ether, amine, amide, imine, sulfoxide, carboxyl, nitrosyl, pyridine, and thioether; and R is hydrogen and R1 is phenyl.
- 31. The method of claim 30 wherein X and X1 are each chloride and L and L1 are each independently selected from the group consisting of P(cyclohexyl)3, P(cyclopentyl)3, P(isopropyl)3, and P(phenyl)3.
- 32. The method of claim 29 wherein the N- heterocyclic carbene ligand is unsaturated.
- 33. A compound formed by attaching a N-heterocyclic carbene ligand to a ruthenium metal carbene metathesis complex comprising:
contacting the N-heterocyclic carbene ligand with a compound of the formula 41wherein X and X1 are either the same or different and are any anionic ligand; R and R1 are either the same or different and are each independently hydrogen or a substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl, wherein each of the substituents is substituted or unsubstituted; and L and L1 are either the same or difference and are any neutral electron donor.
- 34. The compound of claim 33 wherein X and X1 are each independently selected from the group consisting of hydrogen, halogen, substituted moiety and unsubstituted moiety, wherein the moiety is selected from the group consisting of C1-C20 alkyl, aryl, C1-C20 alkoxide, aryloxide, C3-C20 alkyldiketonate, aryldiketonate, C1-C20 carboxylate, arylsulfonate, C1-C20 alkylsulfonate, C1-C20 alkylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl, and wherein the moiety substitution is selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, and aryl;
L and L1 are each independently selected from the group consisting of phosphine, sulfonated phosphine, phosphite, phosphinite, phosphonite, arsine, stibine, ether, amine, amide, imine, sulfoxide, carboxyl, nitrosyl, pyridine, and thioether; and R is hydrogen and R1 is phenyl.
- 35. The compound of claim 34 wherein X and X1 are each chloride and L and L1 are each independently selected from the group consisting of P(cyclohexyl)3, P(cyclopentyl)3, P(isopropyl)3, and P(phenyl)3.
- 36. A product formed by the ROMP of a cyclic olefin monomer using a compound of the formula
- 37. The product of claim 36 wherein the substituent group is substituted with one or more substituted or unsubstituted groups selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, and aryl.
- 38. The product of claim 36 wherein the substituent is functionalized with a moiety selected from the group consisting of hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, carboalkoxy, carbamate, and halogen.
- 39. The product of claim 36 wherein R is hydrogen and R1 is selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, aryl, unsubstituted phenyl, substituted phenyl, unsubstituted vinyl, and substituted vinyl; and wherein the substituted phenyl and substituted vinyl are each independently substituted with one or more groups selected from the group consisting of C1-C5 alkyl, C1-C5 alkoxy, phenyl, hydroxyl, thiol, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, carboalkoxy, and halogen.
- 40. The product of claim 36 wherein L is selected from the group consisting of phosphine, sulfonated phosphine, phosphite, phosphinite, phosphonite, arsine, stibine, ether, amine, amide, imine, sulfoxide, carboxyl, nitrosyl, pyridine, and thioether.
- 41. The product of claim 40 wherein L is selected from the group consisting of P(cyclohexyl)3, P(cyclopentyl)3, P(isopropyl)3, and P(phenyl)3.
- 42. The product of claim 36 wherein X and X1 are each independently selected from the group consisting of hydrogen, halogen, substituted moiety and unsubstituted moiety, wherein the moiety is selected from the group consisting of C1-C20 alkyl, aryl, C1-C20 alkoxide, aryloxide, C3-C20 alkyldiketonate, aryldiketonate, C1-C20 carboxylate, arylsulfonate, C1-C20 alkylsulfonate, C1-C20 alkylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl, and wherein the moiety substitution is selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, and aryl.
- 43. The product of claim 36 wherein X and X1 are each chloride.
- 44. The product of claim 36 wherein R6 and R7 together form a cycloalkyl or an aryl moiety.
- 45. The product of claim 36 wherein R6 and R7 are both hydrogen or phenyl.
- 46. The product of claim 36 wherein R6 and R7 are the same and each is independently of the formula
- 47. The product of claim 46 wherein R8, R9, and R10 are the same and are each methyl.
- 48. The product of claim 36 wherein the cyclic olefin monomer is selected from the group consisting of trisubstituted cyclooctene derivatives, cyclooctatetraene derivatives, cyclopropenes, cyclobutenes, benzocyclobutenes, cyclopentenes, cyclopentadiene oligomers, cyclohexenes, cycloheptenes, cyclooctenes, cycooctadienes, norbornenes, norbornadienes, [2.2.1]bicycloheptenes, [2.2.2]bicyclooctenes, cyclohexenylnorbornenes, and norbornene dicarboxylic anhydrides.
- 49. The product of claim 36 wherein the cyclic olefin monomer is dicyclopentadiene.
Government Interests
[0001] The U.S. Government has certain rights in this invention pursuant to Grant No. 9509745 awarded by the National Science Foundation. This application claims the benefit of U.S. Provisional Patent Application Serial No. 60/127,469, filed Mar. 31, 1999, the contents of which are herein incorporated by reference in its entirety.
Provisional Applications (1)
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Number |
Date |
Country |
|
60127469 |
Mar 1999 |
US |
Divisions (1)
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Number |
Date |
Country |
Parent |
09539840 |
Mar 2000 |
US |
Child |
09770993 |
Jan 2001 |
US |