A New Systematization of the Conformational Behavior of Seven-Membered Rings. Isoclinal Anomeric and Related Orientations

Journal of Organic Chemistry

Volumn 62, Issue 2, 1997, Pages 337-349

  Entrena, A ^a   Campos, J ^a   Gomez J A ^a   Gallo, M A ^a   Espinosa, A ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001291157     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951950j     Document Type: Article

References (89)

1. Conformational Analysis of Seven-Membered Rings. Part 7. For parts 1-6, see refs 7-9, 11, 27, and 32b.
2. Riddell, F. G. The Conformational Analysis of Heterocyclic Compounds; Academic Press: London, 1980.
3. (a) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer Verlag: New York, 1983.
4. (b) Szarek, W. A., Horton, D., Eds. Anomeric Effect. Origins and Consequences; ACS Symposia Series 87; American Chemical Society: Washington, DC, 1979.
5. (c) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Wiley: New York, 1983.
6. (d) Thatcher, G. R. J., Ed. The Anomeric Effect and Associated Stereoelectronic Effects, ACS Symposia Series 539; American Chemical Society: Washington, DC, 1993.
7. (a) Wolfe, S. Acc. Chem. Res. 1972, 5, 102.
8. (b) Juaristi, E. J. Chem. Educ. 1979, 56, 438.
9. (c) Zefirov, N. S.; Gurvich, L. G.; Shashkov, A. E.; Krimer, H. Z.; Vorobeva, E. A. Tetrahedron 1976, 32, 1211.
10. (a) Ermer, O. Aspekte von Kerftfeldrechmungen; Wollfgang Baur Verlag: München, Germany, 1981.
11. (b) Ōsawa, E.; Musso, H. Top. Stereochem. 1982, 13, 117.
12. (c) Burkert, U.; Allinger, N. L. Molecular Mechanics; ACS Monograph No. 177, 1982.
13. (d) Ōsawa, E.; Musso, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 1.
14. (a) Hendrickson, J. B. J. Am. Chem. Soc. 1967, 89, 7036.
15. (b) Bocian, D. F.; Picket, M. M.; Rounds, T. C.; Strauss, H. L. J. Am. Chem. Soc. 1975, 97, 687.
16. (c) Ōsawa, E.; Musso, H. J. Comput. Chem. 1984, 5, 307.
17. Espinosa, A.; Gallo, M. A.; Entrena, A.; Gómez, J. A. J. Mol. Struct. 1994, 323, 247.
18. Espinosa, A.; Gallo, M. A.; Entrena, A.; Campos, J.; Domínguez, J. F.; Camacho, E.; Sánchez, I. J. Mol. Struct. 1993, 296, 133.
19. Espinosa, A.; Gallo, M. A.; Entrena, A.; Gómez, J. A. J. Mol. Struct. 1994, 326, 249.
20. (a) Bocian, D. F.; Strauss, H. L. J. Am. Chem. Soc. 1977, 99, 2876.
21. (b) Kamalov, G. L.; Kuzmin, V. E.; Sharigin, V. N.; Verkhivker, G. M. Vopr. Stereokhim. 1984, 7, 72.
22. Entrena, A.; Jaime, C.; Espinosa, A.; Gallo, M. A. J. Org. Chem. 1989, 54, 1745.
23. (a) Gianni, M. H.; Adams, M.; Kuivila, H. G.; Wurthorn, K. J. Org. Chem. 1975, 40, 450.
24. (b) St-Amour, R.; St-Jacques, M. Can. J. Chem. 1981, 59, 2283.
25. Dionne, P.; St-Jacques, M. Can. J. Chem. 1989, 67, 11.
26. Désilets, S.; St-Jacques, M. J. Am. Chem. Soc. 1987, 109, 1641.
27. Canuel, L.; St-Jacques, M. Can. J. Chem. 1974, 52, 3581.
28. St-Amour, R.; Phan Viet, M. T.; St-Jacques, M. Can. J. Chem. 1984, 62, 2830.
29. Lachapelle, A.; St-Jacques, M. Tetrahedron 1988, 44, 5044.
30. (a) Ménard, D.; St-Jacques, M. Can. J. Chem. 1981, 59, 1160.
31. (b) Ménard, D.; St-Jacques, M. J. Am. Chem. Soc. 1984, 106, 2055.
32. (c) Dionne, P.; St-Jacques, M. J. Am. Chem. Soc. 1987, 109, 2616.
33. (a) Blanchette, A.; Sauriol-Lord, F.; St-Jacques, M. J. Am. Chem. Soc. 1978, 100, 4055.
34. (b) St-Amour, A.; St-Jacques, M. Can. J. Chem. 1983, 61, 109.
35. Edwards, J. T. Chem. Ind. 1955, 1102.
36. Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019.
37. (a) Eliel, E. L.; Giza, C. A. J. Org. Chem. 1968, 33, 3754.
38. (b) Praly, J. P.; Lemieux, R. U. Can. J. Chem. 1987, 65, 213.
39. Perrin, C. L.; Armstrong, K. B.; Fabian, M. A. J. Am. Chem. Soc. 1994, 116, 715.
40. Wolfe, S.; Rauk, A.; Tel, L. M.; Csizmania, I. G. J. Chem. Soc. B 1971, 136.
41. (a) Romers, C.; Altona, C.; Buys, H. R.; Havinga, E. Top. Stereochem. 1969, 4, 39.
42. (b) Kothe, G.; Luger, P.; Paulsen, H. Acta Crystallogr. 1979, B35, 2079.
43. (c) Jeffrey, G. A.; Pople, J. A.; Binkley, J. S.; Vishveshwara, S. J. Am. Chem. Soc. 1978, 100, 373.
44. (d) Fuchs, B.; Scheleifer, L.; Tartakovsky, E. Nouv. J. Chim. 1984, 8, 275.
45. (e) Cossé-Barbi, A.; Dubois, J. E. J. Am. Chem. Soc. 1987, 109, 1503.
46. (f) Cossé-Barbi, E.; Watson, D. G.; Dubois, J. E. Tetrahedron Lett. 1989, 30, 163.
47. Tvarroška, I.; Bleha, T. Adv. Carbohydr. Chem. 1989, 47, 45.
48. Espinosa, A.; Entrena, A.; Gallo, M. A.; Campos, J.; Domínguez, J. F.; Camacho, E.; Garrido, R. J. Org. Chem. 1990, 55, 6018.
49. Juaristi, E. J. Chem. Educ. 1979, 56, 438.
50. Brunck, T. C.; Weinhold, F. J. Am. Chem. Soc. 1979, 101, 1700.
51. (a) Connor, T. M.; Mac Laugchlan, K. A. J. Phys. Chem. 1965, 69, 1888.
52. (b) Snyder, R. G.; Zerbi, G. Spectrochim. Acta 1967, 23A, 391.
53. Mark, J. E.; Flory, P. J. J.Am. Chem. Soc. 1965, 87, 1966; 1966, 88, 3792.
54. Mark, J. E.; Flory, P. J. J.Am. Chem. Soc. 1965, 87, 1966; 1966, 88, 3792.
55. For a study of the anomeric effect on seven-membered rings, see refs 14 and 27. See also: (a) Désilites, S.; St-Jacques, M. Can. J. Chem. 1992, 70, 2650. (b) Entrena, A.; Gallo, M. A.; Espinosa, A.; Jaime, C.; Campos, J.; Domínguez, J. F. J. Org. Chem. 1989, 54, 6034.
56. For a study of the anomeric effect on seven-membered rings, see refs 14 and 27. See also: (a) Désilites, S.; St-Jacques, M. Can. J. Chem. 1992, 70, 2650. (b) Entrena, A.; Gallo, M. A.; Espinosa, A.; Jaime, C.; Campos, J.; Domínguez, J. F. J. Org. Chem. 1989, 54, 6034.
57. For a study of the gauche effect in seven-membered rings, see refs 13, 17c. See also: Dionne, P.; St-Jacques, M. Can. J. Chem. 1990, 68, 513.
58. Hendrickson, J. B. J. Am. Chem. Soc. 1964, 86, 4854.
59. (a) Díez, E.; Esteban, A. L.; Guilleme, J.; Bermejo, F. J. J. Mol. Struct. 1981, 70, 61.
60. (b) Esteban, A. L.; Galiano, C.; Díez, E.; Bermejo, F. J. J. Chem. Soc., Perkin Trans. 2 1982, 657.
61. Cano, F. H.; Foces-Foces, C. J. Mol. Struct. 1983, 94, 209.
62. Hendrickson, J. B. J. Am. Chem. Soc. 1967, 89, 7043.
63. Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354.
64. Boessenkool, I. K.; Boeyens, J. C. A. J. Cryst. Mol. Struct. 1980, 10, 11.
65. Evans, D. G.; Boeyens, J. C. A. Acta Crystallogr. 1989, B45, 581.
66. Hendrickson, J. B. J. Am. Chem. Soc. 1962, 84, 3355.
67. Bucourt, R. Top. Stereochem. 1974, 8, 159.
68. Cremer (Isr. J. Chem. 1980, 20, 12) introduced a more general description of the substituent orientations in relation to the ring as a whole. Nevertheless, Bucourt's and ours allow a more intuitive view of the conformational effect that can appear when substitution is carried out on a seven-membered ring.
69. (a) Allinger, N. L.; Yuh, Y. H.; Lii, J. H. J. Am. Chem. Soc. 1989, 111, 8551.
70. (b) Lii, J. H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8566.
71. (c) Lii, J. H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8576.
72. The MM3(92) program is available from the Technical Utilization Corporation, Inc., 235 Glen Village Court, Powell, OH 43065.
73. Allinger, N. L.; Rahman, M.; Lii, J. H. J. Am. Chem. Soc. 1990, 112, 8293.
74. The β face of oxepane has been considered as that which contains the equatorial hydrogen of C-2 in the TC1 conformation. Once determined, such a criterion has been followed in the substitution of the hydrogen atoms H-2, H-3, and H-4 in the different conformations.
75. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
76. Allinger, N. L.; Chang, S. H. M.; Glaser, D. H.; Honig, D. Isr. J. Chem. 1980, 20, 51.
77. Norskov-Lauritsen, L.; Allinger, N. L. J. Comput. Chem. 1984, 5, 326.
78. The free-energy differences between equatorial and axial methyl and methoxy groups in cyclohexane are respectively 1.74 kcal/mol (Booth, H.; Everett, J. J. Chem. Soc., Chem. Commun. 1976, 278) and 0.75 kcal/mol (Schneider, H. J.; Hoppen, V. Tetrahedron Lett. 1974, 579).
79. The free-energy differences between equatorial and axial methyl and methoxy groups in cyclohexane are respectively 1.74 kcal/mol (Booth, H.; Everett, J. J. Chem. Soc., Chem. Commun. 1976, 278) and 0.75 kcal/mol (Schneider, H. J.; Hoppen, V. Tetrahedron Lett. 1974, 579).
80. (a) Lemieux, R. V.; Pavia, A. A.; Martin, J. C.; Watanabe, K. H.; Can. J. Chem. 1969, 47, 427.
81. (b) Pérez, S.; Marchessault, R. H. Carbohydr. Res. 1978, 65, 114.
82. (c) Booth, H.; Khedahair, K. A.; Readshow, S. A. Tetrahedron 1987, 43, 4699.
83. The α hydrogen atom of C-4 in TC2 conformation is equivalent to the β atom of C-4 in conformation TC9, since both are inverted twist-chair conformations.
84. Espinosa, A.; Gallo, M. A.; Campos, J. An. Quim. 1983, C79, 210.
85. Espinosa, A.; Gallo, M. A.; Campos, J.; Gómez, J. A. Synlett 1995, 11, 1119.
86. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783.
87. Bellringer, F. J.; Bewley, T. Br. Pat. 713,833, 1954; Chem. Abstr., 1958, 50, 6501c.
88. Bellringer, F. J.; Bewley, T. Br. Pat. 713,833, 1954; Chem. Abstr., 1958, 50, 6501c.
89. Piasecki, A. Tetrahedron 1984, 40, 4893.