Theoretical Insights Regarding the Cycloaddition Behavior of Push-Pull Stabilized Carbonyl Ylides

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 2001-2010

  Weingarten, M David ^a   Prein, Michael ^a   Price, Alan T ^a   Snyder, James P ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001697744     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962184z     Document Type: Article

References (70)

1. (a) Padwa, A. Acc. Chem. Res. 1991, 24, 22.
2. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
3. (a) Doyle, M. P. Acc. Chem. Res. 1986, 19, 348.
4. (b) Doyle, M. P. Chem. Rev. 1986, 86, 919.
5. Ando, W. Acc. Chem. Res. 1977, 10, 179.
6. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765.
7. Ye, T.; McKervey, A. Chem. Rev. 1994, 94, 1091.
8. (a) Fang, F. G.; Prato, M.; Kim, G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 3625.
9. (b) Fang, F. G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 2747.
10. (c) Fang, F. G.; Maier, M. E.; Danishefsky, S. J. J. Org. Chem., 1990, 55, 831.
11. (d) Kim, G.; Chu-Moyer, M. Y.; Danishefsky, S. F. J. Am. Chem. Soc. 1990, 112, 2003.
12. Kametani, T.; Yukawa, H.; Honda, T. J. Chem. Soc., Chem. Commun. 1986, 651.
13. (a) Marino, J. P., Jr.; Osterhout, M. H.; Padwa, A. J. Org. Chem. 1995, 60, 2704.
14. (b) Padwa, A.; Price, A. T. J. Org. Chem. 1995, 60, 6258.
15. (a) West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1993, 115, 1177.
16. (b) West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1994, 116, 8420.
17. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513.
18. (a) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696.
19. (b) Davies, H. M. L.; Matasi, J. J. Tetrahedron Lett. 1994, 35, 5209.
20. (c) Davies, H. M. L.; Matasi, J. J.; Ahmed, G. J. Org. Chem. 1996, 61, 2305.
21. Eguchi, M.; Zeng, Q.; Korda, A.; Ojima, I. Tetrahedron Lett. 1993, 34, 915.
22. Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381.
23. Doyle, K. J.; Moody, C. J. Synthesis 1994, 1021.
24. Doyle, M. P.; Kalinin, A. V. Tetrahedron Lett. 1996, 37, 1371.
25. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757.
26. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
27. (a) Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704.
28. (b) Padwa, A. Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072.
29. (c) Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518.
30. (d) Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418.
31. (e) Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
32. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123.
33. (a) Miah, S.; Slawin, A. M. Z.; Moody, C. J.; Richards, I. C.; Sheehan, S. M.; Marino, J. P., Jr.; Semones, M. A.; Padwa, A. Tetrahedron 1996, 52, 2489.
34. (b) Padwa, A.; Price, A. T.; Zhi, L. J. Org. Chem. 1996, 61, 2283.
35. Danishefsky, S.; Singh, R. K. Org. Syn. 1981, 60, 66.
36. The authors have deposited atomic coordinates for structures 10 and 19 with the Cambridge Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
37. Rapoport, H.; Feldman, P. L.; Mayer, M. P. J. Org. Chem. 1985, 50, 5223.
38. (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1967, 6, 733.
39. (b) Taber, D. F.; Ruckle, R. E., Jr.; Hennesy, M. J. J. Org. Chem. 1986, 51, 1663.
40. Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
41. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley-Interscience: New York, 1976.
42. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983.
43. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
44. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Sheehan, S. M. Tetrahedron Lett. 1994, 35, 849.
45. (a) Oppolzer, W.; Fröstl, W. Helv. Chim. Acta 1975, 58, 590.
46. (b) Oppolzer, W.; Fröstl, W.; Weber, H. P. Helv. Chim. Acta 1975, 58, 593.
47. (c) Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204.
48. (a) Houk, K. N. Acc. Chem. Res. 1975, 8, 361.
49. (b) Houk, K. N.; Sims, J.; Watts, C. R.; Luskus, L. J. J. Am. Chem Soc. 1973, 95, 7301.
50. (c) Sustmann, R. Tetrahedron Lett. 1971, 2717.
51. (d) Bastide, J.; Henri-Rousseau, O. Bull. Soc. Chim. Fr. 1973, 2294.
52. (e) Bastide, J.; El Ghandour, N.; Henri-Rousseau, O. Tetrahedron Lett. 1972, 4225.
53. (a) Fukui, K.; Yonezawa, T.; Shingu, H. J. Chem. Phys. 1952, 22, 722.
54. (b) Fukui, K.; Yonezawa, T.; Nagata, C.; Shingu, H. J. Chem. Phys. 1954, 22, 1433.
55. (a) Sustmann, R.; Trill, H. Angew. Chem. Intern. Ed. Engl. 1972, 11, 838.
56. (b) Sustmann, R. Pure Appl. Chem. 1974, 40, 569.
57. (c) Gleittner, J.; Huisgen, R.; Sustmann, R. Tetrahedron Lett. 1977, 881.
58. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209 and 221.
59. Hehre, W. J.; Radom, L.; Schleyer, P. v.R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley and Sons, New York, 1986.
60. Hayes, E. F.; Siu, A. K. Q. J. Am. Chem. Soc. 1971, 93, 2090.
61. Houk, D. N.; Rondan, N. G.; Santiago, C.; Gallo, C. J.; Gandour, R. W.; Griffin, G. W. J. Am. Chem Soc. 1980, 102, 1504.
62. Bobrowicz, F. W.; Goddard, W. A., III The Self-Consistent Field Equations for Generalized Valence Bond and and Open-Shell Hartree-Fock Wave Functions. In Methods of Electronic Structure Theory; Schaefer, H. F., III, Ed.; Plenum: New York, 1977; pp 79-126.
63. Becke, A. D. J. Chem. Phys. 1993, 98, 5648; Stevens, P. J.; Devlin, F. F.; Chablowski, C. F.; Frisch, M. J. J. Chem. Phys.1994, 99, 11623.
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648; Stevens, P. J.; Devlin, F. F.; Chablowski, C. F.; Frisch, M. J. J. Chem. Phys.1994, 99, 11623.
65. Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
66. Bondi, A. J. Phys. Chem. 1964, 68, 441.
67. Spartan 3.1; Wavefunction Inc., 18401 Von Karman #370, Irvine CA. 92715; http://www.wavefun.com/.
68. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 71, 440; http://www.columbia.edu/cu/chemistry/mmod/mmod.html.
69. Frish, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; 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; http://www.gaussian.com/.
70. 3 in the calculations. Though the energies in Table 3 are thereby altered slightly from the experimental system, we have no reason to suspect a change in the qualitatative or semiquantitative outcome.