Cyclizations in the addition of alkylmercury halides to dienes and enynes

Journal of the American Chemical Society

Volumn 118, Issue 41, 1996, Pages 9831-9840

  Russell, Glen A ^a   Li, Chaozhong ^a   Chen, Ping ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; FURAN DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029966161     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9601898     Document Type: Article

References (39)

1. Russell, G. A.; Shi, B. Z.; Kim, B. H.; Jiang, W.; Hu, S.; Baik, W. J. Am. Chem. Soc. 1995, 117, 3952.
2. (a) Russell, G. A.; Li, C.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645.
3. (b) Russell, G. A.; Chen, P.; Yao, C-F.; Kim, B. H. J. Am. Chem. Soc. 1995, 117, 5967.
4. (c) Russell, G. A.; Li, C. Synlett 1996, 699.
5. Russell, G. A.; Hu, S.; Herron, S.; Baik, W.; Ngoviwatchai, P.; Jiang, W.; Nebgen, M.; Wu, Y.-W. J. Phys. Org. Chem. 1988, 1, 299.
6. For reviews of the homolytic addition reactions of 1,6-dienes see: Wilt, J. W. in Free Radicals; Kochi, I. K., Ed.; Wiley: New York, 1973; Vol. I, Chapter 7. Abell, P. I. In Free Radicals; Kochi. J. K., Ed.; Wiley: New York, 1973; Vol. II, Chapter 13. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996; Chapter 2.
7. For reviews of the homolytic addition reactions of 1,6-dienes see: Wilt, J. W. in Free Radicals; Kochi, I. K., Ed.; Wiley: New York, 1973; Vol. I, Chapter 7. Abell, P. I. In Free Radicals; Kochi. J. K., Ed.; Wiley: New York, 1973; Vol. II, Chapter 13. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996; Chapter 2.
8. For reviews of the homolytic addition reactions of 1,6-dienes see: Wilt, J. W. in Free Radicals; Kochi, I. K., Ed.; Wiley: New York, 1973; Vol. I, Chapter 7. Abell, P. I. In Free Radicals; Kochi. J. K., Ed.; Wiley: New York, 1973; Vol. II, Chapter 13. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996; Chapter 2.
9. For a review of tosyl halide radical additions see: Betrand, M. P. Org. Prep. Procedure Int. 1994, 26, 257.
10. Lee, E.; Ko, S. B.; Jung, K. W.; Chang, M. H. Tetrahedron Lett. 1989, 30, 827.
11. Ihara, M.; Taniguchi, N.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1987, 1438. Belletire, J. L.; Mahmoodi, N. O. Tetrahedron Lett. 1984, 30, 4363. Hanessian, S.; Di Fabio, R.; Marcoux, J.-F.; Prod'homme, M. J. Org. Chem. 1990, 55, 3436.
12. Ihara, M.; Taniguchi, N.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1987, 1438. Belletire, J. L.; Mahmoodi, N. O. Tetrahedron Lett. 1984, 30, 4363. Hanessian, S.; Di Fabio, R.; Marcoux, J.-F.; Prod'homme, M. J. Org. Chem. 1990, 55, 3436.
13. Ihara, M.; Taniguchi, N.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1987, 1438. Belletire, J. L.; Mahmoodi, N. O. Tetrahedron Lett. 1984, 30, 4363. Hanessian, S.; Di Fabio, R.; Marcoux, J.-F.; Prod'homme, M. J. Org. Chem. 1990, 55, 3436.
14. Clough, J. M.; Pattenden. G.; Wight, P. C. Tetrahedron Lett. 1989, 30, 7469.
15. Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
16. Blown. C. E.; Günthard, H. H. Chem. Phys. Lett. 1981, 84, 2673. Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1987, 109, 5935.
17. Blown. C. E.; Günthard, H. H. Chem. Phys. Lett. 1981, 84, 2673. Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1987, 109, 5935.
18. Corey, E. J.; Kang, M. J. Am. Chem. Soc. 1984, 106, 5384. Ourmar-Mahimat, H.; Moustrou, C.; Suzur, J.-M.; Bertrand, M. P. J. Org. Chem. 1989, 54, 5684. Snider, B. Chem. Rev. 1996, 96, 339.
19. Corey, E. J.; Kang, M. J. Am. Chem. Soc. 1984, 106, 5384. Ourmar-Mahimat, H.; Moustrou, C.; Suzur, J.-M.; Bertrand, M. P. J. Org. Chem. 1989, 54, 5684. Snider, B. Chem. Rev. 1996, 96, 339.
20. Corey, E. J.; Kang, M. J. Am. Chem. Soc. 1984, 106, 5384. Ourmar-Mahimat, H.; Moustrou, C.; Suzur, J.-M.; Bertrand, M. P. J. Org. Chem. 1989, 54, 5684. Snider, B. Chem. Rev. 1996, 96, 339.
21. Curran, D. F.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. Curran, D. F.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. Nagashima, N. Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo. Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985.
22. Curran, D. F.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. Curran, D. F.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. Nagashima, N. Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo. Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985.
23. Curran, D. F.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. Curran, D. F.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. Nagashima, N. Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo. Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985.
24. Curran, D. F.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. Curran, D. F.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. Nagashima, N. Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo. Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985.
25. Jung, M. E.; Gervoy, J. J. Am. Chem. Soc. 1991, 113, 224. Jung, M. E.; Trifunovich, I. D.; Lensen, N. Tetrahedron Lett. 1992, 33, 6719.
26. Jung, M. E.; Gervoy, J. J. Am. Chem. Soc. 1991, 113, 224. Jung, M. E.; Trifunovich, I. D.; Lensen, N. Tetrahedron Lett. 1992, 33, 6719.
27. Stock, G.; Mah, R. Heterocycles 1989, 28, 723. Sato, T.; Wado, Y.; Nishimoto, N.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1989, 879.
28. Stock, G.; Mah, R. Heterocycles 1989, 28, 723. Sato, T.; Wado, Y.; Nishimoto, N.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1989, 879.
29. 8
30. Saito, S.; Toriumi, Y.; Tomioka, N.; Itai, A. J. Org. Chem. 1995, 60, 4715.
31. All attempts to achieve cyclization failed using t-BuBr/hv at 40°C or t-BuBr/A1BN at 60°C.
32. 2: Jones, K.; Storey, J. M. D. J. Chem. Soc., Chem. Commun. 1992, 1766.
33. 4 L/mol s at 40°C: Russell, G. A.; Ngoviwatchai, P.; Tashtoush, H. I.; Pla-Dalmau, A., Khanna, R. K. J. Am. Chem. Soc. 1988, 110, 3530.
34. Russell, G. A.; Kulkarni, S. V. J. Org. Chem. 1993, 58, 2678.
35. Philip, T.; Cook, R. L.; Malloy, T. B.; Allinger. N. L.; Chang, S.; Yuh, Y. J. Am. Chem. Soc. 1981, 103, 2151.
36. Brown, J. M.; Conn, A. D.; Pilcher, G.; Leitao, M. L. P.; Yang, M.-Y. J. Chem. Soc. Chem. Commun. 1989, 1817.
37. Russell, G. A.; Li, C. Tetrahedron Lett. 1996, 37, 2557.
38. Clive, D. L. J.: Cheshire, D. R. J. Chem. Soc. Chem. Commun. 1987, 1520.
39. Snider, B. B.; Cole, B. M. J. Org. Chem. 1995, 60, 5376.