Shielding effect of carbonyl group and its application to the conformational analysis of 1,1,10,10-tetramethyl[3.3]metacyclophane-2,11-dione

Tetrahedron

Volumn 52, Issue 8, 1996, Pages 2847-2862

  Fukazawa, Yoshimasa ^a   Yang, Yanyan ^a   Hayashibara, Tatsuhiko ^a   Usui, Shuji ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND;

ARTICLE; DRUG STRUCTURE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 0030044981     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00006-3     Document Type: Article

References (71)

1. (a) Karplus, M.J. Chem. Phys. 1959, 30, 11.
2. (b) Garbisch, E. W., Jr. J. Am. Chem. Soc. 1964, 86, 5561.
3. (c) Sternhell, S. Quarterly Rev. 1969, 23, 236.
4. (d) Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783.
5. (e) Jaime, C.; Osawa, E.; Takeuchi, Y.; Camps, P. J. Org. Chem. 1983, 48, 4514.
6. (f) Corey, E. J.; Ponder, J. W. Tetrahedron Lett. 1984, 25, 4325.
7. (g) Masamune, S.; Ma, P.; Moore, R. E.; Fujiyoshi, T.; Jaime, C.; Osawa, E.J. Chem. Soc., Chem. Commun. 1986, 261.
8. (a) Anet, F. A. L.; Boum, A. J. R. J. Am. Chem. Soc. 1965, 87, 5250.
9. (b) Bell, R. A.; Saunders, J. K. Can. J. Chem. 1970, 48, 1114.
10. (c) Hall, L. D.; Sanders, K. M.J. Am. Chem. Soc. 1980, 102, 5703.
11. (d) Scheck, R. M.; Russo, N.; Boelens, R.; Kaptein, R.; van Boom, J. H.J. Am. Chem. Soc. 1983, 105, 2914.
12. (e) Neuhaus, D.; Sheppard, R. N.; Bick, I. R. C. J. Am. Chem. Soc. 1983, 105, 5996.
13. Landis, C.; Allured, U. S, J. Am. Chem. Soc. 1991, 113, 9493.
14. (a) Fukazawa, Y.; Ogata, K.; Usui, S.J. Am. Chem. Soc. 1988, 110, 8692.
15. (b) Okajima, T.; Wang, Z.-H.; Fukazawa, Y. Tetrahedron Lett. 1989, 30, 1551.
16. (c) Okajima, T.; Wang, Z.-H.; Fukazawa, Y. Chemistry Lett. 1991, 37.
17. (d) Fukazawa, Y.; Deyama, K.; Usui, S. Tetrahedron Lett. 1992, 33, 5803.
18. (e) Wang, Z.-H.; Usui, S.; Fukazawa, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1239.
19. (a) Fleischer, U.; Kutzelnigg, W.; Bleiber, A.; Sauer, J.J. Am. Chem. Soc. 1993, 115, 7833.
20. (b) Hinton, J. F.; Guthrie, P.; Pulay, P.; Wolinski, K.J. Am. Chem. Soc. 1992, 114, 1604.
21. (c) Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
22. (a) Toyne, K. J. Tetrahedron 1973, 29, 3889.
23. (b) Lambert, J. B.; Goldstein, J. E. J. Am. Chem. Soc. 1977, 99, 5689.
24. (c) Gschwendtner, W.; Schneider, H.-J.J. Org. Chem. 1980, 45, 3507; Schneider, H.-J.; Schmidt, G.J. Chem. Soc., Perkin Trans. 2 1985, 2027.
25. (c) Gschwendtner, W.; Schneider, H.-J.J. Org. Chem. 1980, 45, 3507; Schneider, H.-J.; Schmidt, G.J. Chem. Soc., Perkin Trans. 2 1985, 2027.
26. (a) Pople, J. A.J. Chem. Phys. 1956, 24, 1111; Bothner-By, A. A.; Pople, J. A. Annual Review of Physical Chemistry 1965, 16, 43.
27. (a) Pople, J. A.J. Chem. Phys. 1956, 24, 1111; Bothner-By, A. A.; Pople, J. A. Annual Review of Physical Chemistry 1965, 16, 43.
28. (b) Bovey, F. A. Nuclear Magnetic Resonance Spectroscopy; Academic Press: New York, 1969; pp. 64-71, 265-274.
29. (c) Wilcox, C. F., Jr.; Farley, E. N.J. Am. Chem. Soc. 1984, 106, 7195; Wilcox, C. F., Jr.; Weber, K. A.J. Org. Chem. 1986, 51, 1088.
30. (c) Wilcox, C. F., Jr.; Farley, E. N.J. Am. Chem. Soc. 1984, 106, 7195; Wilcox, C. F., Jr.; Weber, K. A.J. Org. Chem. 1986, 51, 1088.
31. (a) Abraham, R. J.; Smith, K. M.; Goff, D. A.; Lai, J.-J.J. Am. Chem. Soc. 1982, 104, 4332.
32. (b) Gust, D.; Moore, T. A.; Liddell, P. A.; Nemeth, G. A.; Makings, L. R.; Moore, A. L.; Barrett, D.; Pessiki, P. J.; Bensasson, R. V.; Rougée, M.; Chachaty, C.; De Schryver, F. C.; Van der Auweraer, M.; Holzwarth, A. R.; Connolly, J. S.J. Am. Chem. Soc. 1987, 109, 846.
33. (c) Sanders, G. M.; van Dijk, M.; van Veldhuizen, A.; van der Plas, H. C.; Hofstra, U.; Schaafsma, T. J. J. Org. Chem. 1988, 53, 5272.
34. Fukazawa, Y.; Usui, S.; Tanimoto, K.; Hirai, Y.J. Am. Chem. Soc. 1994, 116, 8169.
35. Fukazawa, Y.; Hayashibara, T.; Yang, Y.; Usui, S. Tetrahedron Lett. 1995, 36, 3349.
36. Fukazawa, Y.; Takeda, Y.; Usui, S.; Kodama, M.J. Am. Chem. Soc. 1988, 110, 7842.
37. Breitenbach, J.; Hoss, R.; Nieger, M.; Rissanen, Vögtle, F. Chem. Ber. 1992, 125, 255.
38. (a)Testa, B. Principle of Organic Stereochemistry; Marcel Decker: New York, 1970; pp. 102-104.
39. (b) Anett; F. A. L.; Kozersky, L.J. Am. Chem. Soc. 1973, 95, 3407.
40. A number of algorithms for generating initial structures was reported; see: (a) Saunders, M.; Houk, K. N.; Wu, Y.-D.; Still, W. C.; Lipton, M.; Chang, G.; Guida, W. C.J. Am. Chem. Soc. 1990, 112, 1419.
41. (b) Goto, H.; Osawa. E.J. Am. Chem. Soc. 1989, 111, 8950.
42. (c) Chang, G.; Guida, W. C.; Still, W. C.J. Am. Chem. Soc . 1989, 111, 4379.
43. (d) Lipton, M.; Still, W. C.J. Comput. Chem. 1989, 9, 343.
44. (e) Still, W. C. In Current Trends in Organic Synthesis; Nozaki, H. Eds.; Pergamon Press: Oxford, U. K., 1983; pp. 233-256.
45. Fukazawa, Y.; Usui, S.; Uchio, Y.; Shiobara, Y.; Kodama, M. Tetrahedron Lett. 1986, 27, 1825.
46. (a) Allinger, N. L.; Yuh, Y. H.; Lii, J.-H.J. Am. Chem. Soc. 1989, 111, 8551.
47. (b) Lii, J.-H.; Allinger, N. L.J. Am. Chem. Soc. 1989, 111, 8566, 8576.
48. (c) Allinger, N. L.; Rahman, M.; Lii, J.-H.J. Am. Chem. Soc. 1990, 112 , 8293.
49. (d) Schmitz, L. R.; Allinger, N. L.J. Am. Chem. Soc. 1990, 112 , 8307.
50. (e) Allinger, N. L.; Chen, K.; Rahman, M.; Pathiaseril, A.J. Am. Chem. Soc. 1991, 113, 4505.
51. (f) Aped, P.; Allinger, N. L.J. Am. Chem. Soc. 1992, 114, 1.
52. (g) Allinger, N. L.; Zhu, Z. S.; Chen, K. J. Am. Chem. Soc. 1992, 114, 6120.
53. (h) Fox, P. C.; Bowen, J. P.; Allinger, N. L.J. Am. Chem. Soc. 1992, 114, 8536.
54. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P.J. Am. Chem. Soc. 1985, 107, 3902.
55. Stewart, J. J. P.J. Comput. Chem. 1989, 10, 210.
56. (a) McConnell, H. M.J. Chem. Phys. 1957, 27, 226.
57. (b) Pople, J. A. Proc. Roy. Soc. 1957, A239, 541, 550.
58. (a) Bothner-By, A. A.; Naar-Colin, C.J. Am. Chem. Soc. 1958, 80, 1728.
59. (b) Buckingham, A. D. Can. J. Chem. 1960, 38, 300.
60. (c) Musher, J. I. J. Chem. Phys. 1962, 37, 34.
61. Zürcher, R. F. Progr. NMR Spectrosc. 1967, 2, 205.
62. ApSimon, J. W.; Demarco, P. V.; Mathieson, D. W.; Craig, W. G.; Karim, A.; Saunders, L.; Whalley, W. B. Tetrahedron, 1970, 26, 119.
63. Schneider, H.-J.; Buchheit, U.; Becker, N.; Schmidt, G.; Siehl, U. J. Am. Chem. Soc. 1985, 107, 7027.
64. (a) ApSimon, J. W.; Beierbeck, H. Can. J. Chrem. 1971, 49, 1328.
65. (b) ApSimon, J. W.; Beierbeck, H.; Todd, D. K. Can. J. Chem. 1972, 50, 2351.
66. 22 suggesting that our simple treatment for the neglect of magnetic anisotropy of C-H bond is proven valid.
67. (a) Sako, K.; Hirakawa, T.; Fujimoto, N.; Shinmyozu, T.; Inazu, T.; Horimoto, H. Tetrahedron Lett. 1988, 29, 6275.
68. (b) Meno, T.; Sako, K.; Suenaga, M.; Mouri, M.; Takemura, H.; Shinmyozu, T.; Inazu, T. Can. J. Chem. 1990, 68, 440.
69. (c) Sako, K.; Shinmyozu, T.; Takemura, H.; Suenaga, M.; Inazu, T.J. Org. Chem. 1992, 57, 6536.
70. -1.; see: (a) Binsch G.; Kessler, H.Angew. Chem. Int. Ed. Engl. 1980, 19, 411.
71. (b) Kessler, H.Angew. Chem. Int. Ed. Engl. 1970, 9, 219.