Synthesis of diacetal trioxa-cage compounds via reaction of bicyclo[2.2.1]heptenes and bicyclo[2.2.2]octenes with dimethyldioxirane

Tetrahedron

Volumn 56, Issue 3, 2000, Pages 341-350

  Lin, Hui Chang ^a   Wu, Hsien Jen ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

Diacetal trioxa cage compounds; Dimethyldioxirane; Lactones

Indexed keywords

ACETAL; ACETAL DERIVATIVE; BICYCLO COMPOUND; DIMETHYLDIOXIRANE; HYDROXYL GROUP; IODINE; LACTONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034645749     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00997-7     Document Type: Article

References (66)

1. For review, see: (a) Eaton, P. E. Angew. Chem., Int. Ed. Engl. 1992, 31, 1421.
2. (b) Griffin, G. W.; Marchand, A. P. Chem. Rev. 1989, 89, 997.
3. (c) Marchand, A. P. Chem. Rev. 1989, 89, 1011.
4. (d) Paquett, L. A. Chem. Rev. 1989, 89, 1051.
5. (e) Klunder, A. J. H.; Zwanenburg, B. Chem. Rev. 1989, 89, 1035.
6. (f) Osawa, E.; Yonemitsu, O. Carbocyclic Cage Compounds; VCH: New York, 1992.
7. (g) Olah, G. A. Cage Hydrocarbons; Wiley: New York, 1990.
8. (a) Meta, G.; Nair, M. S. J. Chem. Soc., Chem. Commun. 1983, 439.
9. (b) Shen, K. W. J. Am. Chem. Soc. 1971, 93, 3064.
10. (c) Allred, E. L.; Beck, B. R. Tetrahedron Lett. 1974, 437.
11. (d) Barborak, J. C.; Khoury, D.; Maier, W. F.; Schleyer, P. V. R.; Smith, E. C.; Smith Jr., W. F.; Wyrick, C. J. Org. Chem. 1974, 44, 4761.
12. (a) Prinzbach, H.; Klaus, M. Angew. Chem., Int. Ed. Engl. 1969, 8, 276.
13. (b) Marchand, A. P.; Reddy, G. M.; Watson, W. H.; Kashyap, R. Tetrahedron 1990, 46, 3409.
14. (a) Sasaki, T.; Eguchi, S.; Kiriyama, T.; Hiroaki, O. Tetrahedron 1974, 30, 2707.
15. (b) Singh, P. J. Org. Chem. 1979, 44, 843.
16. (c) Coxon, J. M.; Fong, S. T.; McDonald, D. Q.; O'Connell, M. J.; Steel, P. J. Tetrahedron Lett. 1991, 32, 7115.
17. (d) Klaus, R. O.; Tobler, H.; Ganter, C. Helv. Chim. Acta 1974, 57, 2517.
18. (e) Ganter, C.; Portmann, R. E. Helv. Chim. Acta 1971, 54, 2069.
19. (f) Stetter, H.; Meissner, H. J.; Last, W. D. Chem. Ber. 1968, 101, 2889.
20. (g) Chow, T. J.; Hon, Y. S.; Jen, C. C.; Liu, S. S.; Chern, J. H.; Lin. K. J. J. Chem. Soc., Perkin Trans. 1 1998, 1095.
21. (h) Speckamp, W. N.; Dijkink, J.; Huisman, H. O. J. Chem. Soc., Chem. Commun. 1970, 197.
22. (i) Deslongchamps, P.; Ruest, L.; Dube, S. Can. J. Chem. 1975, 53, 3613.
23. Suri, S. C. J. Org. Chem. 1993, 55, 4153.
24. (a) Metha, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543.
25. (b) Metha, G.; Nair, M. S. J. Am. Chem. Soc. 1985, 107, 7519.
26. (c) Marchand, A. P.; LaRoe, W. D.; Sharma, G. V. M.; Suri, S. C.; Reddy, D. S. J. Org. Chem. 1986, 51, 1622.
27. (d) Fessner, W. D.; Prinzbach, H. Tetrahedron 1986, 42, 1797.
28. (e) Smith, E. C.; Barborak, J. C. J. Org. Chem. 1976, 41, 1433.
29. (a) Marchand, A. P.; Chou, T. C. Tetrahedron 1975, 31, 2655.
30. (b) Metha, G.; Reddy, K. R. J. Org. Chem. 1987, 52, 460.
31. (a) Metha, G.; Rao, H. S. P. J. Chem. Soc., Chem. Commun. 1986, 472.
32. (b) Metha, G.; Rao, H. S. P.; Reddy, K. R. J. Chem. Soc., Chem. Commun. 1987, 78.
33. Wu, H. J.; Chao, C. S.; Lin, C. C. J. Org. Chem. 1998, 63, 7687.
34. (a) Wu, C. Y.; Lin, C. C.; Lai, M. C.; Wu, H. J. J. Chin. Chem. Soc. 1996, 43, 187.
35. (b) Wu, H. J.; Wu, C. Y.; Lin, C. C. Chin. Chem. Lett. 1996, 7, 15.
36. (a) Wu, H. J.; Lin, C. C. J. Org. Chem. 1995, 60, 7558.
37. (b) Wu, H. J.; Lin, C. C. J. Org. Chem. 1996, 61, 3820.
38. (c) Wu, H. J.; Chern, J. H.; Wu, C. Y. Tetrahedron 1997, 53, 2401.
39. (d) Wu, H. J.; Chern, J. H. Tetrahedron 1997, 53, 17 653.
40. (e) Lin, C. C.; Wu, H. J. Tetrahedron Lett. 1995, 36, 9353.
41. (f) Wu, H. J.; Huang, F. J.; Lin, C. C. J. Chem. Soc., Chem. Commun. 1991, 770.
42. (g) Lin, C. C.; Wu, H. J. J. Chin. Chem. Soc. 1995, 42, 815.
43. (h) Lin, C. C.; Huang, F. J.; Lin, J. C.; Wu, H. J. J. Chin. Chem. Soc. 1996, 43, 177.
44. (i) Lin, R. L.; Wu, C. Y.; Chern, J. H.; Wu, H. J. J. Chin. Chem. Soc. 1996, 43, 289.
45. (j) Chern, J. H.; Wu, H. J.; Wang, S. L.; Liao, F. L. J. Chin. Chem. Soc. 1998, 45, 139.
46. Lin, C. C.; Wu, H. J. Synthesis 1996, 715.
47. (a) Wu, H. J.; Wu, C. Y. Tetrahedron Lett. 1997, 38, 2493.
48. (b) Wu, H. J.; Wu, C. Y. J. Org. Chem. 1999, 64, 1576.
49. (c) Mehta, G.; Vidya, R. Tetrahedron Lett. 1997, 38, 4173.
50. (a) Wu, H. J.; Chern, J. H. J. Org. Chem. 1997, 62, 3208.
51. (b) Wu, H. J.; Chern, J. H. J. Chem. Soc., Chem. Commun. 1997, 547.
52. (c) Wu, H. J.; Chern, J. H. Tetrahedron Lett. 1997, 38, 2887.
53. (d) Chern, J. H.; Wu, H. J. J. Chin. Chem. Soc. 1997, 44, 71.
54. (e) Chern, J. H.; Wu, H. J. Tetrahedron 1998, 54, 5967.
55. (a) Lin, H. C.; Wu, C. Y.; Wu, H. J. J. Chin. Chem. Soc. 1997, 44, 609.
56. (b) Yen, C. H.; Tsai, S. H.; Wu, H. J. J. Chin. Chem. Soc. 1998, 45, 799.
57. (a) Wu, H. J.; Tsai, S. H.; Chern, J. H.; Lin, H. C. J. Org. Chem. 1997, 62, 6367.
58. (b) Wu, H. J.; Tsai, S. H.; Chung, W. S. Tetrahedron Lett. 1996, 37, 8209.
59. (c) Wu, H. J.; Tsai, S. H.; Chung, W. S. J. Chem. Soc., Chem. Commun. 1996, 375.
60. Tsai, S. H.; Wu, H. J.; Chung, W. S. J. Chin. Chem. Soc. 1996, 43, 445.
61. Murthy, Y. V. S. N.; Pillai, C. N. Synth. Commun. 1996, 26, 2363.
62. (a) Williams, P. D.; LeGoff, E. J. Org. Chem. 1981, 46, 4143.
63. (b) Williams, P. D.; LeGoff, E. Tetrahedron Lett. 1985, 26, 1367.
64. (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205.
65. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187.
66. Curci, R.; D'Accolti, L.; Fiorentino, M.; Fusco, C.; Adam, W.; Gonzalez-Nunez, M. E.; Mello, R. Tetrahedron Lett. 1992, 33, 4225.