Computational modeling of renewable molecules. Ruthenium alkylidene-mediated metathesis of trialkyl-substituted olefins

Organometallics

Volumn 29, Issue 7, 2010, Pages 1580-1587

  Fomine, Serguei ^a   Tlenkopatchev, Mikhail A ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLIDENES; COMPUTATIONAL MODELING; DICHLOROETHANE; DOUBLE BONDS; ELECTRONIC FACTORS; GRUBBS CATALYSTS; KINETIC CONTROL; METALLACARBENE; METATHESIS REACTIONS; REACTION UNDER; REACTIVE INTERMEDIATE; RELATIVE STABILITIES; RUTHENIUM ALKYLIDENES; STERIC EFFECT; STERIC FACTOR; TRANSITION STATE;

CATALYSTS; OLEFINS; REACTION INTERMEDIATES; RUTHENIUM;

ACTIVATION ENERGY;

EID: 77950851956     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om900848q     Document Type: Article

References (61)

1. Tanaka, Y.; Hirasawa, H. Chem. Phys. Lipids 1989, 51, 183
2. Takigawa, T.; Ibata, K.; Mizuno, M. Chem. Phys. Lipids 1989, 51, 171
3. Jaenicke, L.; Siegmund, H.-U. Chem. Phys. Lipids 1989, 51, 159
4. Jankowski, W. J.; Swiezewska, E.; Sasak, W.; Chojnacki, T. J. Plant Physiol. 1994, 143, 448
5. Baldenius, K. U.; von dem Bussche-Hünnefeld, L.; Hilgemann, E.; Hoppe, P.; Stürmer, R. In Ullmanns Encyclopedia of Industrial Chemistry, VCH Verlagsgesellschaft: Weinheim, 1966; Vol. 7, pp 478-488, 594-597.
6. Rüttimann, A. Chimia 1986, 40, 290
7. Stevens, P. M. Polymer Chemistry; Oxford University Press Inc.: New York, 1999; pp 35-37, 169-170, 252-254.
8. Chatterjee, A. K. In Handbook of Metathesis-Applications in Organic Synthesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2, pp 246-295.
9. Ikeda, H.; Matsumoto, S.; Enyo, H. ACS Symposium Series 59; American Chemical Society: Washington, D.C., 1977; Chapter 21.
10. Alimuniar, A.; Yarmo, M. A.; Ab. Rahman, M. Z.; Kohjiya, S.; Ikeda, Y.; Yamashita, S. Polym. Bull. (Berlin) 1990, 23, 119
11. Ast, W.; Hummel, K. Naturwissenschaften 1970, 57, 545
12. Hummel, K.; Kiattanavith, N.; Bernard, E. Angew. Makromol. Chem. 1993, 207, 137
13. Kiattanavith, N.; Hummel, K. Polym. Degrad. Stab. 1993, 41, 1
14. Korshak, Yu.V.; Tlenkopatchev, M. A.; Dolgoplosk, B. A.; Avdeikina, E. G.; Kutepov, D. F. J. Mol. Catal. 1982, 15, 207
15. Korshak, Yu.V.; Tlenkopatchev, M. A. Mendeleev Chem. J. 1989, 34, 665
16. Gutiérrez, S.; Vargas, S. M.; Tlenkopatchev, M. A. Polym. Degrad. Stab. 2004, 83, 149
17. Wagener, K. B.; Puts, R. D.; Smith, D. W. Makromol. Chem., Rapid Commun. 1991, 12, 419
18. Konzelman, J.; Wagener, K. B. Macromolecules 1995, 28, 4686
19. Thorn-Csanyi, E. Rubber Chem. Technol. 1994, 67, 786
20. Thorn-Csanyi, E.; Hummer, J.; Zilles, J. U. Macromol. Chem., Rapid Commun. 1994, 15, 797
21. Thorn-Csanyi, E.; Zilles, J. U. J. Mol. Catal. A: Chem. 2002, 190, 85
22. Lapinte, V.; Fontaine, L.; Montembault, V.; Campistron, I.; Reyx, D. J. Mol. Catal. A: Chem. 2002, 190, 117
23. Solanky, Sh. S.; Campistron, I.; Laguerre, A.; Pilard, J.-F. Macromol. Chem. Phys. 2005, 206, 1057
24. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003.
25. Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900
26. Frenzel, U.; Nuyken, O. J. Polym. Sci. Part A Polym. Chem. 2002, 40, 2895
27. Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565
28. Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012
29. Bielawski, C. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 2000, 39, 2903
30. W. Craig, S.; Manzer, J. A.; Coughlin, E. B. Macromolecules 2001, 34, 7929
31. Magolan, J.; Coster, M. J. J. Org. Chem. 2009, 74, 5083
32. Pahari, P; Rohr, J. J. Org. Chem. 2009, 74, 2750
33. Hodgson, D. M.; Angrish, D.; Erickson, S. P.; Kloesges, J.; Lee, C. H. Org. Lett. 2008, 10, 5553
34. Zhang, Y.; Gaekwad, J.; Wolfert, M. A.; Geert-Jan Boons, G.-J. Org. Biomol. Chem. 2008, 6, 3371
35. Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751
36. Michrowska, A.; Bujok, R.; Harutyunyan, S.; Sashuk, V.; Dolgonos, G.; Grela, K. J. Am. Chem. Soc. 2004, 126, 9318
37. Netscher, T. J. Organomet. Chem. 2006, 691, 5155
38. Fomine, S.; Tlenkopatchev, M. A. J. Organomet. Chem. 2001, 630, 157
39. Fomine, S.; Tlenkopatchev, M. A. Appl. Catal A: Gen. 2009, 355, 148
40. Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, CA, 1997.
41. Suresh, C. H.; Koga, N. Organometallics 2004, 23, 76
42. Fomine, S.; Vargas, S. M.; Tlenkopatchev, M. A. Organometallics 2003, 22, 93
43. Vyboishchikov, S. F.; Buhl, M.; Thiel, W. Chem.-Eur. J. 2002, 8, 3962
44. Cavallo, L. J. J. Am. Chem. Soc. 2002, 124, 8965
45. Fomine, S.; Vargas, J.; Tlenkopatchev, M. A. Organometallics 2005, 24, 5691
46. Fomine, S.; Vargas, J.; Tlenkopatchev, M. A. J. Organomet. Chem. 2006, 691, 3343
47. Fomine, S.; Vargas, J.; Tlenkopatchev, M. A. J. Mol. Catal. A 2007, 263, 121
48. Fomine, S.; Tlenkopatchev, M. A. Organometallics 2007, 26, 4491
49. Adlhart, C.; Chen, P. J. Am. Chem. Soc. 2004, 126, 3496
50. Jordaan, M.; van Helden, P.; van Sittert, C. G. C. E.; Vosloo, H. C. M. J. Mol. Catal. A: Chem. 2006, 254, 145
51. Stewart, I. C.; Benitez, D.; O'Leary, D. J.; Tkatchouk, E.; Day, M. W.; Goddard, W. A., 3rd; Grubbs, R. H. J. Am. Chem. Soc. 2009, 131, 1931
52. Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749
53. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543
54. Hinderling, C.; Adlhart, C.; Chen, P. Angew. Chem. 1998, 110, 2831
55. Hinderling, C.; Adlhart, C.; Chen, P. Angew. Chem., Int. Ed. 1998, 37, 2685
56. Adlhart, C.; Hinderling, C.; Baumann, H.; Chen, P. J. Am. Chem. Soc. 2000, 122, 8204
57. Adlhart, C.; Volland, M. A. O.; Hofmann, P.; Chen, P. Helv. Chim. Acta 2000, 83, 3306
58. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G. J.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, Rev. E.01; Gaussian, Inc.: Wallingford, CT, 2004.
59. Boydston, A. J.; Xia, Y.; Kornfield, J. A.; Gorodetskaya, I. A.; Grubbs, R. H. J. Am. Chem. Soc. 2008, 130, 12775
60. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
61. Jaguar, Version 7.0; Schrodinger, LLC: New York, 2007.