Comparative DFT study on the role of conformers in the ruthenium alkylidene-catalyzed ROMP of norborn-2-ene

Journal of Physical Organic Chemistry

Volumn 21, Issue 11, 2008, Pages 963-970

  Naumov, Sergej ^a   Buchmeiser, Michael R ^a,b  

^a LEIBNIZ INSTITUTE OF SURFACE ENGINEERING IOM   (Germany)

^b UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Alkylidenes; Grubbs catalysts; Quantum chemical calculations; Ring opening metathesis polymerization (ROMP); Ruthenium

Indexed keywords

ABS RESINS; CATALYSIS; CATALYSTS; HYDROCARBONS; LIGANDS; MONOMERS; OLEFINS; POLYMERS; QUANTUM CHEMISTRY; RATE CONSTANTS; RHENIUM COMPOUNDS; RING OPENING POLYMERIZATION; RUTHENIUM;

ACTIVE CONFORMATIONS; ALKYLIDENES; CARBENE; CARBENE COMPLEXES; CONFORMATIONAL PROPERTIES; CYCLIC ALKENES; CYCLOBUTANES; DFT STUDIES; ELECTRON INTERMEDIATES; GRUBBS CATALYSTS; IN DEPENDENCES; QUANTUM CHEMICAL CALCULATIONS; RATE LIMITING BARRIERS; REACTION PATHWAYS; RELATIVE STABILITIES; RING-OPENING METATHESIS POLYMERIZATION (ROMP); RUTHENIUM ALKYLIDENE;

CHLORINE COMPOUNDS;

EID: 55849133013     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1407     Document Type: Article

References (60)

1. A. Fürstner, Angew. Chem. 2000, 112, 3140-3172.
2. R. H. Grubbs, Handbook of Metathesis Vol. 1-3, 1st edn, Wiley-VCH, Weinheim, 2003.
3. R. H. Grubbs, Tetrahedron 2004, 60(34), 7117-7140.
4. K. J. Ivin, J. C. Mol, Olefin Metathesis and Metathesis Polymerization, Academic Press, San Diego, 1997, 1-472.
5. M. R. Buchmeiser, Chem. Rev. 2000, 100(4), 1565-1604.
6. Y. Chauvin, Angew. Chem. 2006, 118(23), 3824-3831.
7. R. H. Grubbs, Angew. Chem. 2006, 118(23), 3845-3850.
8. R. R. Schrock, Angew. Chem. 2006, 118(23), 3832-3844.
9. T. W. Baughman, K. B. Wagener, Progr. Polymer Sci. 2005, 176, 1-42.
10. C. W. Bielawski, R. H. Grubbs, Adv. Polym. Sci. 2007, 32(1), 1-29.
11. M. R. Buchmeiser, Adv. Polymer. Sci. 2005, 176, 89-120.
12. L. Ackermann, A. Furstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999; 40(26), 4787-4790.
13. J. Huang, E. D. Stevens, S. P. Nolan, J. L. Petersen, J. Am. Chem. Soc. 1999, 121, 2674-2678.
14. J. Louie, R. H. Grubbs, Angew. Chem. 2001, 113(1), 253-255.
15. M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250.
16. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34(1), 18-29.
17. T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. Int. Ed. 1999, 38(16), 2416-2419.
18. T. Weskamp, W. C. Schattenmann, M. Spiegler, W. A. Herrmann, Angew. Chem. 1998, 110(18), 2631-2633.
19. C. Adlhart, R Chen, Helv. Chim. Acta 2003, 86(4), 941-949.
20. C. Adlhart, M. A. O. Volland, P. Hofmann, P. Chen, Helv. Chim. Acta 2000, 83(12), 3306-3311.
21. J. A. Love, M. S. Sanford, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 10103-10109.
22. M. S. Sanford, J. A. Love, R. H. Grubbs, Organometallics 2001, 20(25), 5314-5318.
23. M. S. Sanford, M. Ulman, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 749-750.
24. M. S. Sanford, J. A. Love, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 6543-6554.
25. M. A. O. Volland, S. M. Hansen, F. Rominger, P. Hofmann, Organometallics 2004, 23(4), 800-816.
26. M. A. O. Volland, R Hofmann, Helv. Chim. Acta 2001, 84(11), 3456-3469.
27. S. L. Bolton, J. E. Williams, M. B. Sponsler, Organometallics 2007, 26, 2485-2487.
28. A. G. Wenzel, R. H. Grubbs, J. Am. Chem. Soc. 2006, 128, 16048-16049.
29. C. Adlhart, P. Chen, J. Am. Chem. Soc. 2004, 126(11), 3496-3510.
30. F. Bernardi, A. Bottoni, G. R Miscione, Organometallics 2003, 22(5), 940-947.
31. L. Cavallo, J. Am. Chem. Soc. 2002, 124, 8965-8973.
32. J. N. Coalter, J. C. Bollinger, J. C. Huffman, U. Werner-Zwanziger, K. G. Caulton, E. R. Davidson, H. Gerard, E. Clot, O. Eisenstein, New J. Chem. 2000, 24(1), 9-26.
33. S. Famine, J. V. Ortega, M. A. Tlenkopatchev, Organometallics 2005, 24(23), 5696-5701.
34. S. Fomine, J. V. Ortega, M. A. Tlenkopatchev, J. Mol. Catal. A:Chem. 2005, 236(1-2), 156-161.
35. S. Fomine, J. V. Ortega, M. A. Tlenkopatchev, J. Organomet. Chem. 2006, 691(15), 3343-3348.
36. S. Fomine, J. V. Ortega, M. A. Tlenkopatchev, J. Mol, Catal. A: Chem. 2007, 263(1-2), 121-127.
37. S. Fomine, M. A. Tlenkopatchev, J. Organomet. Chem. 2006, 691(24-25), 5189-5196.
38. S. Fomine, M. A. Tlenkopatchev, Organometallics 2007, 26, 4491-4497.
39. S. Famine, S. M. Vargas, M. A. Tlenkopatchev, Organometallics 2003, 22(1), 93-99.
40. S. F. Vyboishchikov, M. Bühl, W. Thiel, Chem. Eur. J. 2002, 8(17), 3962-3975.
41. S. F. Vyboishchikov, W. Thiel, Chem. Eur. J. 2005, 11, 3921-3935.
42. T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111(16), 2573-2576.
43. C. Adlhart, P. Chen, Angew. Chem. Int. Ed. 2002, 41(23), 4484-4487.
44. M. Piacenza, L Hyla-Kryspin, S. Grimme, J. Comput. Chem. 2007, 28(14), 2275-2285.
45. J. J. Lippstreu, B. F. Straub, J. Am. Chem. Soc. 2005, 127(20), 7444-7457.
46. A. C. Tsipis, A. G. Orpen, J. N. Harvey, Dalton Trans. 2005, 2849-2858.
47. B. F. Straub, Angew. Chem. Int Ed. 2005, 44(37), 5974-5978.
48. B. F. Straub, Angew. Chem. 2005, 117, 6129-6132.
49. B. F. Straub, Adv. Synth. Catal. 2007, 349(1-2), 204-214.
50. A. D. Becke, J. Chem. Phys. 1993, 98(7), 5648-5652.
51. A. D. Becke, J. Chem. J. Phys. 1996, 104(3), 1040-1046.
52. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37(2), 785-789.
53. Jaguar 6.5; Schrodinger LLC NY, NY, (2005).
54. W. R. Wadt, P. J. Hay, J. Chem. Phys. 1985, 82(1), 284-298.
55. M. R. Buchmeiser, D. Wang, Y. Zhang, S. Naumov, K. Wurst, Eur. J. Inorg. Chem. 2007, 25, 3988-4000.
56. M. R. Buchmeiser, D. R. Wang, S. Naumov, K. Wurst, J. Organomet. Chem. 2006, 691(24-25), 5391-5396.
57. B. J. Lynch, P. L. Fast, M. Harris, D. G. Truhlar, J. Phys. Chem. A 2000, 104(21), 4811-4815.
58. X. Xu, A. William, I. Goddard, Proc. Natl. Acad. Sci. USA 2004, 101(9), 2673-2677.
59. O. M. Aagaard, R. J. Meier, F. Buda, J. Am. Chem. Soc. 1998, 120, 7174-7182.
60. T.-L. Choi, R. H. Grubbs, Angew. Chem. 2003, 115, 1785-1788.