Conjugatively stabilized bridgehead olefins: Formation and reaction of remarkably stable homoadamant-3-enes substituted with phenyl and methoxycarbonyl groups

Journal of the American Chemical Society

Volumn 118, Issue 30, 1996, Pages 7075-7082

  Ohno, Masatomi ^a   Itoh, Motohiro ^a   Umeda, Masami ^a   Furuta, Ryoji ^a   Kondo, Kazumoto ^a   Eguchi, Shoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE;

ARTICLE; DRUG STABILITY; DRUG STRUCTURE; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE;

EID: 0029744631     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953977q     Document Type: Article

References (77)

1. (a) Fawcett, F. S. Chem. Rev. 1950, 47, 219.
2. (b) Koebrich, G. Angew. Chem. 1973, 85, 494.
3. (c) Keese, R. Angew. Chem., Int. Ed. Eng. 1975, 14, 528.
4. (d) Buchanan, G. L. Chem. Soc. Rev. 1974, 3, 41.
5. (e) Shea, K. J. Tetrahedron 1980, 36, 1683.
6. (f) Szeimies, G. Reactive Intermediate; Abramovitch, R. A., Ed.; Plenum Press: New York, 1983; Vol. 3, p 299.
7. (g) Warner, P. M. Chem. Rev. 1989, 89, 1067.
8. (h) Keese, R.; Luef, W. Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; J. Wiley & Sons: New York, 1991; Vol. 20, p 231.
9. Wiseman, J. R.; Pletcher, W. A. J. Am. Chem. Soc. 1970, 92, 956.
10. Maier, W. F.; Schleyer, P. R. J. Am. Chem. Soc. 1981, 103, 1891.
11. For recent examples of the bridgehead olefin, see: (a) Shea, K. J.; Cooper D. K.; England, W. P.; Ziller, J. W.; Lease, T. G. Tetrahedron Lett. 1990, 31, 6843.
12. (b) Chiang, Y.; Kresge, A. J.; Walsh, P. A. J. Org. Chem. 1990, 55, 1309.
13. (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850.
14. (d) Detert, H.; Anthony-Mayer, C.; Meier, H. Angew Chem., Int. Ed. Engl. 1992, 31, 791.
15. (e) Wijsman, G. W.; Wolf, W. H.; Bickelhaupt, F.; Kooijman, H.; Spek, A. J. Am. Chem. Soc. 1992, 114, 9191.
16. (f) Lease, T. G.; Shea, K. J. J. Am. Chem. Soc. 1993, 115, 2248.
17. (g) Gudipati, M. S.; Radziszewski, J. G.; Kaszynski, P.; Michl, J. J. Org. Chem. 1993, 58, 3668.
18. (h) Bunz, U.; Herpich, W.; Podlech, J.; Polborn, K.; Pratzel, A., Stephenson. D. S.; Szeimies, G. J. Am. Chem. Soc. 1994, 116, 7637.
19. (a) Renzoni. G. E.; Yin, T.-K.; Borden, W. T. J. Am. Chem. Soc. 1986, 108, 7121.
20. (b) Yin, T.-K.; Radziszewski, J. G.; Renzoni, G. E.; Downing, J. W.; Michl, J.; Borden, W. T. J. Am. Chem. Soc. 1987, 109, 820.
21. (c) Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1988, 110, 4710.
22. (d) Radziszewski, J. G.; Yin, T.-K.; Renzoni, G. E.; Hrovat, D. A.; Borden, W. T.; Michl. J. J. Am. Chem. Soc. 1993, 115, 1454.
23. (a) Gano, J. E.; Eizenberg, L. J. Am. Chem. Soc. 1973, 95, 972.
24. (b) Alberts, A. H., Strating, J.; Wynberg, H. Tetrahedron Lett. 1973, 3047.
25. (c) Burns, W.; Grant, G.; McKervey, M. A.; Step, G. J. Chem. Soc., Perkin Trans. I 1976, 234.
26. (d) Martella, D. J.; Jones, M., Jr.; Schleyer, P. R. J. Am. Chem. Soc: 1978, 100, 2896.
27. (e) Cadgan, J. I. G.; Leardini, R. J. Chem. Soc., Chem. Commun. 1979, 783.
28. (f) Conlin, R. T.; Miller, R. D.; Michl, J. J. Am. Chem. Soc. 1979, 101, 7637.
29. (g) Gillespie, D. G.; Walker, B. J. J. Chem. Soc., Perkin Trans. I 1983, 1689.
30. (h) Lenoir, D.; Kornrumpf, W.; Fritz, H. P. Chem. Ber. 1983, 116, 2390.
31. (i) Michl, J.; Radziszewski, J. G.; Downing, J. W.; Kopecky, J.; Kaszynski, P.; Miller, R. D. Pure Appl. Chem. 1987, 59, 1613.
32. (j) Bian, N.; Jones, M., Jr. J. Am. Chem. Soc. 1995, 117, 8957.
33. (a) Farcasiu, M.; Farcasiu, D.; Conlin, R. T.; Jones, M., Jr.; Schleyer, P. R. J. Am. Chem. Soc: 1973, 95, 8207.
34. (b) Adams, B. L.; Kovacic, P. J. Am. Chem. Soc: 1973, 95, 8206.
35. (c) Adams, B. L.; Kovacic, P. J. Org. Chem. 1974, 39, 3090.
36. (d) Adams, B. L.; Kovacic, P. J. Am. Chem. Soc. 1974, 96, 7014.
37. (e) Martella, D. J.; Jones, M., Jr.; Schleyer, P. R.; Maier, W. F. J. Am. Chem. Soc. 1979, 101, 7634.
38. (f) Klebach, T. C.; Jones, M., Jr.; Kovacic, P. Tetrahedron Lett. 1977, 22, 497.
39. (g) Sellers, S. F.; Klebach. T. C.; Hollowood, F.; Jones, M., Jr. J. Am. Chem. Soc. 1982, 104, 5492.
40. (h) Myers, D. R. Senthilnathan, V. P.; Platz, M. S.; Jones, M., Jr. J. Am. Chem. Soc. 1986, 108, 4232.
41. (i) Bly, R. S.; Bly, R. K.; Hossain. M. M.; Lebioda, L.; Raja, M. J. Am. Chem. Soc. 1988, 110, 7723.
42. 2. However, the yield of 7 was low, as estimated from the cycloadduct 11 (34% yield), and the long reaction time (2 h) resulted in the formation of byproducts [e.g., α-(1-adamantyl)benzyl alcohol].
43. Regitz, M.; Maas, G. Diazo Compounds; Academic Press: Orlando, 1981; Chapter 13.
44. Rubin, Y.; Lin, S. S.; Knobler, C. B.; Anthony, J.; Boldi, A. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 6943.
45. McMahon, R. J.; Abelt, C. J.; Champman, O. L.; Johnson, J. W.; Kreil, C. L.; LeRoux, J.-P.; Mooring, A. M.; West, P. R. J. Am. Chem. Soc. 1987, 109, 2456.
46. (a) House, H. O.; Outcalt, R. J.; Haack, J. L.; VanDerveer, D. J. Org. Chem. 1983, 48, 1654.
47. (b) Bartlett, P. D.; Ganavali, R. J. J. Org. Chem. 1991, 56, 6043.
48. (c) Smith, J. M.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 3816.
49. 1H NMR signals of the products (16: δ 6.21. 35: δ 3.49) to those of an internal standard (benzyl ether: δ 4.56).
50. Concentration of the solution: ca. 0.035 M.
51. (a) Padwa, A.; Austin, D. J.; Price, A. T.; Semonnes, M. A.; Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Tran, A. J. Am. Chem. Soc. 1993, 115, 8669.
52. (b) Brown, D. S.; Eliott, M. C.; Moody, C. J.; Mowlem, T. J.; Marino, J. P., Jr.; Padwa, A. J. Org. Chem. 1994, 59, 2447.
53. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
54. See also: (d) Cox, G. G.; Haigh, D.; Hindley, R. M.; Miller D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 3139. (e) Pirrung, M. C.; Morehead, A. T., Jr. J. Am. Chem. Soc. 1994, 116, 8991.
55. See also: (d) Cox, G. G.; Haigh, D.; Hindley, R. M.; Miller D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 3139. (e) Pirrung, M. C.; Morehead, A. T., Jr. J. Am. Chem. Soc. 1994, 116, 8991.
56. (a) Davies, H. M. Tetrahedron 1993, 49, 5203.
57. (b) Davies, H. M.; Hu, B.; Saikali, E.; Bruzinski, P. R. J. Org. Chem. 1994, 59, 4535.
58. Fort, R. C., Jr. Adamantane, The Chemistry of Diamond Molecules; Marcel Dekker: New York, 1976: p 193.
59. s symmetry
60. Mlinaric-Majerski, K.; Kaselj, M. J. Org. Chem. 1994, 59, 4362.
61. Rasoul, H. A. A.; Hall, H. K., Jr. J. Org. Chem. 1982, 47, 2080.
62. Lwowski, W. 1,3-Dipolar Cycloaddition Chemistry; Padwa A., Ed.; J. Wiley & Sons: New York, 1984; Vol. 1, Chapter 5.
63. Eaton, P. E.; White, A. J. J. Org. Chem. 1990, 55, 1321.
64. Glaser, R.; Chen, G. S.; Barnes, C. L. J. Org. Chem. 1993, 58, 7446.
65. 4-H signal was described simply as a triplet. However, it is split in a more complicated fashion and structures cannot be assigned simply by referring to the data given therein: Krasutskii, P. A.; Seinenova, I. G.; Safronova, E. E.; Novikova, M. I.; Yurchenko, A. G. Zh. Org. Khim. 1989, 25, 2336.
66. Danishefsky, S.; Nagasawa, K.; Wang, N. J. Org. Chem. 1975, 40, 1989.
67. 2) was previously reported to stabilize the bicyclo[3.3.1]non-1-en-3-one system: see ref 12a.
68. MOPAC Ver 5.00 (QCPE No. 445): Stewart J. J. P. QCPE Bull. 1989, 9, 10. Hirano, T. JCPE Newsletter 1989, 9(2), 36. Revised as Ver 5.01 by J. Toyoda for Apple Macintosh. HyperChem. 4.0 (Hypercube Inc.) on an IBM compatible computer.
69. MOPAC Ver 5.00 (QCPE No. 445): Stewart J. J. P. QCPE Bull. 1989, 9, 10. Hirano, T. JCPE Newsletter 1989, 9(2), 36. Revised as Ver 5.01 by J. Toyoda for Apple Macintosh. HyperChem. 4.0 (Hypercube Inc.) on an IBM compatible computer.
70. H° caused by substituting phenyl and methoxycarbonyl groups for a hydrogen are assumed to be about - 1 to - 4 kcal/mol (cf. Jesen, J. L. Prog. Phys. Org. Chem. 1976, 12. 189), the OS's of 1 and 2 can be estimated to be slightly lower than that of 3.
71. 13C NMR as soon as Rh-catalyzed decomposition was complete. Although the sample used was a crude product, olefinic signals could be distinguished from noisy signals due to contaminants.
72. Compounds 47 and 48 were prepared from cyclohexanone and the corresponding phosphonate reagents according to previously reported procedures - for 47: Shakak, I.; Almong, J.; Bergman, E. D. Isr. J. Chem. 1969, 9, 585. For 48: Courout, P.; Ghribi, A. Synthesis 1991, 790.
73. Compounds 47 and 48 were prepared from cyclohexanone and the corresponding phosphonate reagents according to previously reported procedures - for 47: Shakak, I.; Almong, J.; Bergman, E. D. Isr. J. Chem. 1969, 9, 585. For 48: Courout, P.; Ghribi, A. Synthesis 1991, 790.
74. 1H NMR signals were observed at δ 1.41-2.52 (15 H, m) and 7.12-7.37 (5 H, m) for 1 and at δ 1.45-2.20 (15 H, m) and 3.70 (3 H, s) for 2.
75. Johnson, S. A.; Hunt, H. R.; Newmann H. M. Inorg. Chem. 1963, 2, 960.
76. Doyle, M. P.; Bagheri, V.; Wandless, T. J.; Harn, N. K.; Brinker D. A.; Eagle, C. T.; Loh, K.-L. J. Am. Chem. Soc. 1990, 112, 1906.
77. Stetter, H.; Rauscher, E. Chem. Ber 1960, 93, 1161.