Theoretical calculations on the Wittig reaction revisited

Journal of the American Chemical Society

Volumn 120, Issue 30, 1998, Pages 7530-7536

  Yamataka, Hiroshi ^a   Nagase, Shigeru ^b  

^a OSAKA UNIVERSITY   (Japan)

^b TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORANE DERIVATIVE;

ARTICLE; CALCULATION; DRUG STRUCTURE; ELECTRON TRANSPORT; MOLECULAR DYNAMICS; REACTION ANALYSIS; THERMODYNAMICS;

EID: 0032486777     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja974237f     Document Type: Article

References (51)

1. Among recent reviews of the Wittig reaction, see: (a) Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993. (b) Maryanoff, B.; Reitz, A. E. Chem. Rev. 1989, 89, 863.
2. Among recent reviews of the Wittig reaction, see: (a) Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993. (b) Maryanoff, B.; Reitz, A. E. Chem. Rev. 1989, 89, 863.
3. For a leading mechanistic review, see: Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1.
4. (a) Vedejs, E.; Snoble, K. A. J. J. Am. Chem. Snc. 1973, 75, 5778.
5. (b) Vedejs, E.; Meier, G. P.; Snoble, K. A. J. J. Am. Chem. Soc. 1981, 103, 2823.
6. (c) Reitz, A. B.; Mutter, M. S.; Maryanoff, B. E. J. Am. Chem. Soc. 1984, 106, 1873.
7. (d) Maryanoff, B. E.; Reitz, A. B.; Mutter, M. S.; Inners, R. R.; Almond, H. R., Jr.; Whittle, R. R.; Olofson, R. A. J. Am. Chem. Soc. 1986, 108, 7664.
8. Vedejs, E.; Fleck, T. J. J. Am. Chem. Soc. 1989, 111, 5861.
9. Among others, see: Schlosser, M. Top. Stereochem. 1970, 5, 1. Reitz, A.; Nortey, S. O.; Jordan, A. D.; Mutter, M. S.; Maryanoff, B. E. J. Org. Chem. 1986, 51, 3302.
10. Among others, see: Schlosser, M. Top. Stereochem. 1970, 5, 1. Reitz, A.; Nortey, S. O.; Jordan, A. D.; Mutter, M. S.; Maryanoff, B. E. J. Org. Chem. 1986, 51, 3302.
11. Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron 1967, 23, 2709. Alien, D. W.; Ward, H. Tetrahedron Lett. 1979, 29, 2707. McEwen, W. E.; Cooney, J. V. J. Org. Chem. 1983, 48, 983. McEwen, W. E.; Beaver, B. D. Phosphorus Sulfur Relat. Elem. 1985, 24, 259. Mylona, A.; Nikokavouras, J.; Takakis, I. M. J. Org. Chem. 1988, 53, 3838. Ward, W. J., Jr.; McEwen, W. E. J. Org. Chem. 1990, 55, 473.
12. Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron 1967, 23, 2709. Alien, D. W.; Ward, H. Tetrahedron Lett. 1979, 29, 2707. McEwen, W. E.; Cooney, J. V. J. Org. Chem. 1983, 48, 983. McEwen, W. E.; Beaver, B. D. Phosphorus Sulfur Relat. Elem. 1985, 24, 259. Mylona, A.; Nikokavouras, J.; Takakis, I. M. J. Org. Chem. 1988, 53, 3838. Ward, W. J., Jr.; McEwen, W. E. J. Org. Chem. 1990, 55, 473.
13. Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron 1967, 23, 2709. Alien, D. W.; Ward, H. Tetrahedron Lett. 1979, 29, 2707. McEwen, W. E.; Cooney, J. V. J. Org. Chem. 1983, 48, 983. McEwen, W. E.; Beaver, B. D. Phosphorus Sulfur Relat. Elem. 1985, 24, 259. Mylona, A.; Nikokavouras, J.; Takakis, I. M. J. Org. Chem. 1988, 53, 3838. Ward, W. J., Jr.; McEwen, W. E. J. Org. Chem. 1990, 55, 473.
14. Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron 1967, 23, 2709. Alien, D. W.; Ward, H. Tetrahedron Lett. 1979, 29, 2707. McEwen, W. E.; Cooney, J. V. J. Org. Chem. 1983, 48, 983. McEwen, W. E.; Beaver, B. D. Phosphorus Sulfur Relat. Elem. 1985, 24, 259. Mylona, A.; Nikokavouras, J.; Takakis, I. M. J. Org. Chem. 1988, 53, 3838. Ward, W. J., Jr.; McEwen, W. E. J. Org. Chem. 1990, 55, 473.
15. Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron 1967, 23, 2709. Alien, D. W.; Ward, H. Tetrahedron Lett. 1979, 29, 2707. McEwen, W. E.; Cooney, J. V. J. Org. Chem. 1983, 48, 983. McEwen, W. E.; Beaver, B. D. Phosphorus Sulfur Relat. Elem. 1985, 24, 259. Mylona, A.; Nikokavouras, J.; Takakis, I. M. J. Org. Chem. 1988, 53, 3838. Ward, W. J., Jr.; McEwen, W. E. J. Org. Chem. 1990, 55, 473.
16. Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron 1967, 23, 2709. Alien, D. W.; Ward, H. Tetrahedron Lett. 1979, 29, 2707. McEwen, W. E.; Cooney, J. V. J. Org. Chem. 1983, 48, 983. McEwen, W. E.; Beaver, B. D. Phosphorus Sulfur Relat. Elem. 1985, 24, 259. Mylona, A.; Nikokavouras, J.; Takakis, I. M. J. Org. Chem. 1988, 53, 3838. Ward, W. J., Jr.; McEwen, W. E. J. Org. Chem. 1990, 55, 473.
17. Yamataka, H.; Nagareda, K.; Ando, K.; Hanatusa, T. J. Org. Chem. 1992, 57, 2865.
18. Schlosser, M.; Schaub, B. J. Am. Chem. Soc. 1982,. 104, 5821.
19. Bestmann, H. J. Pure Appl. Chem. 1980, 52, 771.
20. Marí, F.; Lahti, P. M.; McEwen, W. E. J. Am. Chem. Soc. 1992, 114, 813.
21. Vedejs, E.; Marth, C. F. J. Am. Chem. Soc. 1988, 110, 3948.
22. Yamataka. H.; Nagareda, K.; Takatsuka, T.; Ando, K.; Hanafusa, T.; Nagase, S. J. Am. Chem. Soc. 1993, 115, 8570.
23. Yamataka, H.; Fujimura, N.; Kawafuji, Y.; Hanafusa, T. J. Am. Chem. Soc. 1987, 109, 4305. Yamataka, H.; Sasaki, D.; Kuwatani, Y.; Mishima, M.; Tsuno, Y. J. Am. Chem. Soc. 1997, 119, 9975.
24. Yamataka, H.; Fujimura, N.; Kawafuji, Y.; Hanafusa, T. J. Am. Chem. Soc. 1987, 109, 4305. Yamataka, H.; Sasaki, D.; Kuwatani, Y.; Mishima, M.; Tsuno, Y. J. Am. Chem. Soc. 1997, 119, 9975.
25. Eades, R. A.; Gassman, P. G.; Dixon, D. A. J. Am. Chem. Soc. 1981, 103, 1066. Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1984, 106, 5805. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250. Glaser, R.; Choy, G. S.-C.; Hall, M. K. J. Am. Chem. Soc. 1991, 113, 1109. Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. Dixon, D. A. In Ylides and Imines of Phosphorus; Johnson, A. W., Ed.; Wiley; New York, 1993; Chapter 2.
26. Eades, R. A.; Gassman, P. G.; Dixon, D. A. J. Am. Chem. Soc. 1981, 103, 1066. Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1984, 106, 5805. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250. Glaser, R.; Choy, G. S.-C.; Hall, M. K. J. Am. Chem. Soc. 1991, 113, 1109. Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. Dixon, D. A. In Ylides and Imines of Phosphorus; Johnson, A. W., Ed.; Wiley; New York, 1993; Chapter 2.
27. Eades, R. A.; Gassman, P. G.; Dixon, D. A. J. Am. Chem. Soc. 1981, 103, 1066. Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1984, 106, 5805. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250. Glaser, R.; Choy, G. S.-C.; Hall, M. K. J. Am. Chem. Soc. 1991, 113, 1109. Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. Dixon, D. A. In Ylides and Imines of Phosphorus; Johnson, A. W., Ed.; Wiley; New York, 1993; Chapter 2.
28. Eades, R. A.; Gassman, P. G.; Dixon, D. A. J. Am. Chem. Soc. 1981, 103, 1066. Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1984, 106, 5805. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250. Glaser, R.; Choy, G. S.-C.; Hall, M. K. J. Am. Chem. Soc. 1991, 113, 1109. Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. Dixon, D. A. In Ylides and Imines of Phosphorus; Johnson, A. W., Ed.; Wiley; New York, 1993; Chapter 2.
29. Eades, R. A.; Gassman, P. G.; Dixon, D. A. J. Am. Chem. Soc. 1981, 103, 1066. Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1984, 106, 5805. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250. Glaser, R.; Choy, G. S.-C.; Hall, M. K. J. Am. Chem. Soc. 1991, 113, 1109. Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. Dixon, D. A. In Ylides and Imines of Phosphorus; Johnson, A. W., Ed.; Wiley; New York, 1993; Chapter 2.
30. Eades, R. A.; Gassman, P. G.; Dixon, D. A. J. Am. Chem. Soc. 1981, 103, 1066. Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1984, 106, 5805. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250. Glaser, R.; Choy, G. S.-C.; Hall, M. K. J. Am. Chem. Soc. 1991, 113, 1109. Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. Dixon, D. A. In Ylides and Imines of Phosphorus; Johnson, A. W., Ed.; Wiley; New York, 1993; Chapter 2.
31. Eades, R. A.; Gassman, P. G.; Dixon, D. A. J. Am. Chem. Soc. 1981, 103, 1066. Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Gassman, P. G. J. Am. Chem. Soc. 1983, 105, 7011. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1984, 106, 5805. Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250. Glaser, R.; Choy, G. S.-C.; Hall, M. K. J. Am. Chem. Soc. 1991, 113, 1109. Bachrach, S. M. J. Org. Chem. 1992, 57, 4367. Dixon, D. A. In Ylides and Imines of Phosphorus; Johnson, A. W., Ed.; Wiley; New York, 1993; Chapter 2.
32. (a) Mari, F.; Lahti, P. M.; McEwen, W. E. Heteroatom Chem. 1990, 1, 255.
33. (b) Mari, F.; Lahti, P. M.; McEwen, W. E. Heteroatom Chem. 1991, 2, 265.
34. (c) Yamataka, H.; Hanafusa, T.; Nagase, S.; Kurakake, T. Heteroatom Chem. 1991, 2, 465.
35. Höller, R.; Lischka, H. J. Am. Chem. Soc. 1980, 102, 4632. Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1984, 106, 6117. Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1.
36. Höller, R.; Lischka, H. J. Am. Chem. Soc. 1980, 102, 4632. Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1984, 106, 6117. Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1.
37. Höller, R.; Lischka, H. J. Am. Chem. Soc. 1980, 102, 4632. Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1984, 106, 6117. Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1.
38. Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080.
39. Maryanoff, B. E.; Reitz, A. B. Phosphorus Sulfur 1986, 27, 167. Reitz, A. B.; Nortey, S. O.; Jordan, A. D.; Mutter, M. S.; Maryanoff, B. E. J. Org. Chem. 1986, 51, 3302.
40. Maryanoff, B. E.; Reitz, A. B. Phosphorus Sulfur 1986, 27, 167. Reitz, A. B.; Nortey, S. O.; Jordan, A. D.; Mutter, M. S.; Maryanoff, B. E. J. Org. Chem. 1986, 51, 3302.
41. Pietro, W. J.; Francl, M. M.; Hehre, W. J.; DeFrees, D. J.; Pople, J. A.; Binkley, J. S. J. Am. Chem. Soc. 1982, 104, 5039.
42. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
43. (a) Becke, A. D. Phys. Rev. 1988, A38, 3098.
44. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
45. Francl, M. N.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654.
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; DeFrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez C.; Pople, J. A. Gaussian 94; Gaussian Inc.: Pittsburgh. PA, 1995.
47. Van Hook W. A. In Isotope Effects in Chemical Reactions; Collins, C. J., Bowman, N. S., Eds.; Van Nostrand-Reinhold: New York, 1970; Chapter 1.
48. The electronic energy and the free energy of the initial complex are -6.6 and 3.8 kcal/mol at HF/3-21G, -4.8 and 4.8 kcal/mol at HF/3-21G*, and -3.3 and 5.8 kcal/mol at B3LYP/6-31G*, respectively, for the cis OP forming process of eq 3; the complex is more stable than the reactant state in terms of electronic energy, but it is less stable in terms of free energy and it most likely does not exist as a bound species. The free energy of activation is positive (20.4 kcal/mol at HF/3-21G* and 16.7 kcal/mol at B3LYP/6-31G*). The relative stabilities of the trans/cis TSs are almost the same for electronic energy, enthalpy, and free energy, and we use the ΔE‡ values in this paper.
49. Melander, L.; Saunders: W. H., Jr. Reaction Rates of Isotopic Molecules; Wiley: New York, 1780. Fry, A. In Isotope Effects in Chemical Reactions; Collins, C. J., Bowman, N. S., Eds.; Van Nostrand-Reinhold: New York, 1970; Chapter 6.
50. Melander, L.; Saunders: W. H., Jr. Reaction Rates of Isotopic Molecules; Wiley: New York, 1780. Fry, A. In Isotope Effects in Chemical Reactions; Collins, C. J., Bowman, N. S., Eds.; Van Nostrand-Reinhold: New York, 1970; Chapter 6.
51. Yamataka, H.; Matsuyama, T.; Hanafusa, T. J. Am. Chem. Soc. 1989, 111, 4912.