Distortion in the structures of 5-azaadamantanone and its N-oxide: Implication on diastereofacial selectivity

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 232-236

  Gung, Benjamin W ^a   Wolf, Mark A ^a  

^a MIAMI UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001517922     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9517297     Document Type: Article

References (43)

1. (a) Srivastava, S.; le Noble, W. J. J. Am. Chem. Soc. 1987, 109, 5874.
2. (b) Chung, W. S.; Turro, N. J.; Srivastava, S ; Li, H.; le Noble, W. J. J. Am. Chem. Soc. 1988, 110, 7882-3
3. (c) Bodepudi, V.; le Noble, W. J. J. Org. Chem. 1991, 56, 2001.
4. (d) Li, H.; Mehta, G.; Padma, S.; le Noble, W. J. J Org Chem. 1991, 56, 2007.
5. Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916.
6. Adcock, W.; Cotton, J.; Trout, N. A. J. Org. Chem., 1994, 59, 1867-1876.
7. Laube, T.; Hollenstein, S. Helv. Chim. Acta 1994, 77, 1773-80.
8. Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5876.
9. (a) Cieplak, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447.
10. (b) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
11. (a) Wu, Y. D.; Tucker, J. A.; Houk, K. N. J. Am. Chem. Soc 1991, 113, 5018.
12. (b) Paddon-Row, M. N., Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10638-10639.
13. Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. Aust. J. Chem. 1991, 44, 765-770.
14. Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1991, 327-330. Aust. J. Chem. 1991, 44, 765-770.
15. Wipf, P.; Kim, Y. J. Am. Chem. Soc. 1994, 116, 11678-11688.
16. Fernandez, M. J.; Galvez, E.; Lorente, A.; Soler, J. A.; Florencio, F.; Sanz, J. J. Heterocycl. Chem. 1989, 26, 349.
17. McCabe, P. H.; Milne, N. J.; Sim, G. A. Acta Crystallogr. 1989, C45, 114.
18. Goncharov, A. V.; Panov, V. N.; Maleev, A. V.; Potekin, K. A.; Kurkutova, E. N.; Struchkov, Y. T.; Palyvulin, V. A.; Zefirov, N. S. Dokl. Akad. Nauk. SSSR 1991, 318, 907-910.
19. Hehre, W. J.; Radom, L.; Schleyer, P. v. P.; Pople, J. A. Ab initio Molecular Orbital Theory, Wiley, New York, 1986.
20. Gung, B. W.; Wolf, M. A.; Mareska, D. A.; Karipides, A. J Org. Chem., 1994, 59, 4899.
21. 3 addition to 3 has appeared. However, distortion of the ground state configuration was not discussed. See: Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418-427.
22. Gaussian 92, Revision B, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1992.
23. Still, W. C. MacroModel 2.5, Columbia University.
24. Anh, N. T. Top. Curr. Chem. 1980, 88, 145.
25. (a) Mukherjee, D.; Wu, Y-D.; Fronczek, F. R.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 3328.
26. (b) Wu, Y-D.; Houk, K. N. J. Am. Chem Soc. 1987, 109, 908.
27. There is an early report of a crystal structure of adamantanone in the plastic phase. Unfortunately, the crystal was orientationally disordered and the X-ray diffraction data were interpreted with assumptions leading to obvious error. Amoureux, J P.; Bee, M. J. Phys. C 1980, 13, 3577-83.
28. For theoretical studies, see: (a) Radom, L.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1972, 94, 2371. (b) Dill, J. D.; Schleyer, P. v. P.; Pople, J. A. J. Am. Chem. Soc. 1976, 98, 1663. (c) Schleyer, P. v. P.; Kos, A. J. Tetrahedron, 1983, 39, 1141. (d) Bingham, R. C. J. Am. Chem. Soc. 1975, 97, 6743. (e) Hoffmann, R., Radom, L.; Pople, J. A.; Schleyer, P. v. P.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221.
29. For theoretical studies, see: (a) Radom, L.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1972, 94, 2371. (b) Dill, J. D.; Schleyer, P. v. P.; Pople, J. A. J. Am. Chem. Soc. 1976, 98, 1663. (c) Schleyer, P. v. P.; Kos, A. J. Tetrahedron, 1983, 39, 1141. (d) Bingham, R. C. J. Am. Chem. Soc. 1975, 97, 6743. (e) Hoffmann, R., Radom, L.; Pople, J. A.; Schleyer, P. v. P.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221.
30. For theoretical studies, see: (a) Radom, L.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1972, 94, 2371. (b) Dill, J. D.; Schleyer, P. v. P.; Pople, J. A. J. Am. Chem. Soc. 1976, 98, 1663. (c) Schleyer, P. v. P.; Kos, A. J. Tetrahedron, 1983, 39, 1141. (d) Bingham, R. C. J. Am. Chem. Soc. 1975, 97, 6743. (e) Hoffmann, R., Radom, L.; Pople, J. A.; Schleyer, P. v. P.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221.
31. For theoretical studies, see: (a) Radom, L.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1972, 94, 2371. (b) Dill, J. D.; Schleyer, P. v. P.; Pople, J. A. J. Am. Chem. Soc. 1976, 98, 1663. (c) Schleyer, P. v. P.; Kos, A. J. Tetrahedron, 1983, 39, 1141. (d) Bingham, R. C. J. Am. Chem. Soc. 1975, 97, 6743. (e) Hoffmann, R., Radom, L.; Pople, J. A.; Schleyer, P. v. P.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221.
32. For theoretical studies, see: (a) Radom, L.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1972, 94, 2371. (b) Dill, J. D.; Schleyer, P. v. P.; Pople, J. A. J. Am. Chem. Soc. 1976, 98, 1663. (c) Schleyer, P. v. P.; Kos, A. J. Tetrahedron, 1983, 39, 1141. (d) Bingham, R. C. J. Am. Chem. Soc. 1975, 97, 6743. (e) Hoffmann, R., Radom, L.; Pople, J. A.; Schleyer, P. v. P.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221.
33. For an experimental study, see: (f) Rahman, M M.; Lemal, D. M ; Dailey, W. P. J. Am. Chem. Soc. 1988, 110, 1964.
34. Shen, M.; Schaefer, H. F., III; Liang, C.; Lii, J. H.; Allinger, N. L.; Schleyer, P. v. R. J. Am Chem. Soc 1992, 114, 497.
35. Kelly, D. P.; Aherne, K.; Delgado, F.; Giansiracusa, J. J.; Jensen, W. A.; Karavokiros, R. A.; Mantello, R. A.; Reum, M E. J. Am. Chem. Soc. 1993, 115, 12010.
36. (a) Burgi, H. B.; Dunitz, J. D.; Shefter, E. J. J. Am. Chem. Soc. 1973, 95, 5065.
37. (b) Burgi, H. B.; Lehn, J. M.; Wipff, G. J. Am. Chem. Soc. 1974, 96, 1956-1957.
38. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
39. (b) Cherest, M.; Felkin, H., Tetrahedron Lett. 1968, 2205.
40. Liotta, C L.; Burgess, E. M.; Eberhardt, W H. J. Am. Chem. Soc. 1984, 106, 4849-4852.
41. (a) Mori, I.; Bartlett, P. A.; Heathcock, C. H. J Am. Chem. Soc. 1987, 109, 7199.
42. (b) Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2819.
43. Pross, A.; Radom, L.; Riggs, N. V. J. Am. Chem. Soc. 1980, 102, 2253-2259.