Competitive alkylidene transfer to olefins and alkylidene-to-olefin interconversion of the electrophilic iron carbene complexes [FeCp(CO)(L)(=CHR)] + (L = CO, PH3; R = Me, Et): A theoretical study

Organometallics

Volumn 23, Issue 26, 2004, Pages 6281-6287

  Dazinger, Georg ^a   Kirchner, Karl ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

COMPETITION; COMPLEXATION; ISOMERIZATION; MOLECULAR STRUCTURE; PROPANE; REACTION KINETICS; STEREOCHEMISTRY; THERMODYNAMICS;

CYCLOPROPANES; LIGANDS; ORBITAL CONTROL; STEREOSELECTIVITY;

OLEFINS;

EID: 11044222002     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049374h     Document Type: Article

References (51)

1. (a) Brookhart, M.; Nelson, G. O. J. Am. Chem. Soc. 1977, 99, 6099.
2. (b) Brookhart, M.; Tucker J. R.; Flood, T. C.; Jensen J. J. Am. Chem. Soc. 1980, 102, 1203.
3. (c) Brookhart, M.; Humphrey, M. B.; Kratzer, H. J.; Nelson, G. O. J. Am. Chem. Soc. 1980, 102, 7802.
4. (d) Brookhart, M.; Tucker, J. R.; Husk, G. R. J. Am. Chem. Soc. 1981, 103, 979.
5. (e) Brookhart, M.; Tucker, J. R.; Husk, G. R. J. Am. Chem. Soc. 1983, 105, 268.
6. (f) Brookhart, M.; Studebaker, W. B.; Husk, G. R. Organometallics 1985, 4, 943.
7. Kremer, K. A. M.; Kuo, G.-H.; O'Connor, E. J.; Helquist, P.; Kerber, R. C. J. Am. Chem. Soc. 1982, 104, 6119.
8. (a) Casey, C. P.; Miles, W. H.; Tukada, H.; O'Connor, J. M. J. Am. Chem. Soc. 1985, 107, 2924.
9. (b) Casey, C. P.; Miles, W. H.; Tukada, H.; O'Connor, J. M. J. Am. Chem. Soc. 1982, 104, 3761.
10. Bly, R. S.; Bly, R. K. J. Chem. Soc., Chem. Commun. 1986, 1046.
11. (a) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
12. (b) Doyle, M. P. Chem. Rev. 1986, 86, 919.
13. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
14. (b) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
15. (c) Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785.
16. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; 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.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gausgian, Inc.: Pittsburgh, PA, 1998.
17. Brookhart, M.; Buck, R. J. Am. Chem. Soc. 1989, 111, 559.
18. (a) Seemann, J. I.; Davies, S. G. J. Am. Chem. Soc. 1985, 107, 6533.
19. (b) Seemann, J. I.; Davies, S. G. Tetrahedron Lett. 1984, 1845.
20. (c) Seemann, J. I.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1984, 1019.
21. Farnum, D. G. Adv. Phys. Org. Chem. 1075, 11, 123.
22. Fenske, R. F. In Organometallic Compounds: Synthesis, Structure, and Theory; Shapiro, B. L., Ed.; Texas A&M University Press: College Station, TX, 1983.
23. For tunneling in hydrogen shift reactions see: Hess, B. A., Jr. J. Org. Chem. 2001, 66, 5897, and references therein.
24. (a) Kirchner, K.; Calhorda, M. J.; Schmid, R.; Veiros, L. F. J. Am. Chem. Soc. 2003, 125, 11721.
25. (b) Cadierno, V.; Dies, J.; Garcia-Alvarez, J.; Gimeno, J.; Calhorda, M. J.; Veiros, L. F. Organometallics 2004, 23, 2421.
26. Hammond, G. S. J. Am. Chem. Soc. 1954, 77, 334.
27. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5646.
28. (b) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
29. (c) Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785.
30. (a) Haeusermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 78, 1211.
31. (b) Kuechle, W.; Dolg, M.; Stoll, H.; Preuss, H. J. Chem. Phys. 1994, 100, 7535.
32. (c) Leininger, T.; Nicklass, A.; Stoll, H.; Dolg, M.; Schwerdtfeger, P. J. Chem. Phys. 1996, 105, 1052.
33. For other examples where the B3LYP functional (with the sdd basis for Fe) has provided reliable results see: Khoroshun, D. V.; Musaev, D. G.; Vreven, T.; Morokuma, K. Organometallics 2001, 20, 2007.
34. (a) McClean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
35. (b) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
36. (c) Wachters, A. H. Chem. Phys. 1970, 52, 1033.
37. (d) Hay, P. J. J. Chem. Phys. 1977, 66, 4377.
38. (e) Raghayachari, K.; Trucks, G. W. J. Chem. Phys. 1989, 91, 1062.
39. (f) Binning, R. C.; Curtiss, L. A. J. Comput. Chem. 1995, 103, 6104.
40. (g) McGrath, M. P.; Radom, L. J. Chem. Phys. 1991, 94, 511.
41. (a) Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 4 9.
42. (b) Peng, C. Schlegel, H. B. Isr. J. Chem. 1994, 33, 449.
43. (a) Carpenter, J. E.; Weinhold, F. J. Mol. Struct. (THEOCHEM) 1988, 169, 41.
44. (b) Carpenter, J. E. Ph.D. Thesis, University of Wisconsin, Madison, WI, 1987.
45. (c) Foster, J. P.; Weinhold, F. J. Am. Chem, Soc. 1980, 102, 7211.
46. (d) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066.
47. (e) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 1736.
48. (f) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
49. (g) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
50. (h) Weinhold, F.; Carpenter, J. E. The Structure of Small Molecules and Ions; Plenum: New York, 1988; p 227.
51. Wiberg, K. B. Tetrahedron 1968, 24, 1083.