Claims
- 1. A method for preparing a dicyano compound by metathesis chemistry, the method comprising the steps of:(a) providing allyl cyanide substrate; (b) providing a ruthenium-based catalyst capable of catalyzing the metathesis condensation of the allyl cyanide substrate; (c) contacting the allyl cyanide substrate with the catalyst to form a reaction mixture; and (d) placing the reaction mixture under conditions that result in the formation of a olefin product via metathesis condensation, the functionalized allylic olefin product having a different chemical structure than the allyl cyanide substrate.
- 2. The method of claim 1, wherein the catalyst is 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ruthenium benzylidene (Ru*).
- 3. The method of claim 2, wherein the allyl cyanide substrate has an electron rich functional group.
- 4. The method of claim 2, wherein the olefin product is 1,4-dicyanobutene.
- 5. The method of claim 1, wherein the step (d) of placing the reaction mixture under conditions that result in the formation of the olefin product via metathesis condensation comprises placing the reaction mixture at a temperature of between about 10° C. and 70° C.
- 6. The method of claim 1, wherein the step (d) of placing the reaction mixture under conditions that result in the formation of the olefin product via metathesis condensation comprises placing the reaction mixture at a temperature of about 23° C. or less.
- 7. The method of claim 1, wherein the step (d) of placing the reaction mixture under conditions that result in the formation of the olefin product via metathesis condensation comprises placing the reaction mixture under about standard atmospheric pressure.
- 8. The method of claim 1, wherein the step (d) of placing the reaction mixture under conditions that result in the formation of the olefin product via metathesis condensation comprises applying a vacuum force to the reaction mixture.
- 9. The method of claim 1, wherein the step (d) of placing the reaction mixture under conditions that result in the formation of the olefin product via metathesis condensation comprises placing the reaction mixture under an inert atmosphere.
- 10. The method of claim 9, wherein the inert atmosphere is selected from N2 or Ar.
- 11. The method of claim 1, wherein the step (d) of placing the reaction mixture under conditions that result in the formation of the olefin product via metathesis condensation is performed under anhydrous conditions.
- 12. The method of claim 1, wherein substrate:catalyst ratio (mol:mol) is between about 1:1 to 1000:1.
- 13. The method of claim 1, wherein substrate:catalyst ratio (mol:mol) is greater than about 10:1.
- 14. The method of claim 1, further comprising a step (e) of hydrogenating the olefin product.
- 15. The method of claim 14, wherein the step (e) of hydrogenating the olefin product is catalyzed using residue of the ruthenium-based catalyst formed during the step (d) of placing the reaction mixture under conditions that result in the formation of olefin product via metathesis condensation.
- 16. The method of claim 15, wherein the olefin product is 1,4-dicyanobutene, and the step (e) of hydrogenating the olefin product results in the production of 1,4-dicyanobutane.
CROSS REFERENCE TO RELATED APPLICATIONS
The present application is a division of U.S. patent application Ser. No. 09/849,100 filed May 4, 2001, now U.S. Pat. No. 6,521,799, entitled “Metathesis of Functionalized Allylic Olefins,” which claims the benefit of U.S. provisional patent application No. 60/201,918 filed May 4, 2000 and entitled “Metathesis Dimerization of Functionalized Allylic Olefins.”
STATEMENT AS TO FEDERALLY SPONSORED RESEARCH
This invention was made with United States Government support awarded by the Army Research Office, Grant No. DAAG55-97-1-0023; and by the National Science Foundation, Division of Materials Research, Grant No. DMR-9806492. The United States Government has certain rights in this invention.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
6159890 |
Nubel et al. |
Dec 2000 |
A |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/201918 |
May 2000 |
US |