Cyclization of N-butyl-4-pentenylaminyl: Implications for the cyclization of alkenylaminyl radicals

Journal of the American Chemical Society

Volumn 118, Issue 18, 1996, Pages 4276-4283

  Maxwell, Brendan J ^a   Tsanaktsidis, John ^a  

^a CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

N BUTYL 4 PENTENYLAMINYL; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; ENERGY TRANSFER; REACTION ANALYSIS;

EID: 0010439815     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953720s     Document Type: Article

References (47)

1. (a) Motherwell, W. B.; Crich, D. Free-Radical Reactions in Organic Synthesis; Academic Press: London, 1992.
2. (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 715-831.
3. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
4. (d) Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron, 1990, 46, 1385.
5. (e) Ghosez, A.; Giese, B.; Mehl, W.; Metzger, J. O.; Zipse, H. In Methoden der Organischen Chemie, C-Radikale; Regitz, M., Giese, B., Eds. Georg Thieme: Stuttgart 1989; Vol. E 19a, Parti.
6. (a) Rajanbabu, T. V. Acc. Chem. Rev. 1991, 24, 139.
7. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1986.
8. Beckwith, A. L. J. Tetrahedron 1981, 3073 and references therein.
9. (a) Esker, J. L.; Newcomb, M. Adv Heterocycl. Chem. 1993, 58, 1.
10. (b) Newcomb, M.; Horner, J. H.; Shahin, H. Tetrahedron Lett. 1993, 34, 5523.
11. Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493.
12. (d) Newcomb, M.; Deeb, T. M.; Marquardt, D. J. Tetrahedron 1990, 46, 2317.
13. (e) Newcomb, M.; Burchill, M. T.; Deeb, T. M. J. Am. Chem. Soc. 1988, 110, 6528.
14. (f) Newcomb, M.; Deeb, T. M. J. Am. Chem. Soc. 1987, 109, 3163.
15. (g) Newcomb, M.; Park, S.-U.; Kaplan, J.; Marquardt, D. J. Tetrahedron Lett. 1985, 20, 5651.
16. (h) Newcomb, M.; Marquardt, D. J.; Deeb, T. M. Tetrahedron 1990, 46, 2329.
17. (a) Tokuda, M.; Fujita, H.; Suginome, H. J. Chem. Soc., Perkin Trans. 1 1994, 777.
18. (b) Tokuda, M.; Miyamoto, T.; Fujita, H.; Suginome, H. Tetrahedron 1991, 47, 747.
19. Tokuda, M.; Yamada, Y.; Takagi, T.; Suginome, H. Tetrahedron 1987, 43, 281.
20. (a) Kim, S.; Yoon, K. S.; Kim, S. S.; Seo, H. S. Tetrahedron 1995, 51, 8437.
21. (b) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521.
22. (c) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1993, 115, 3328.
23. (a) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron 1994, 50, 1275.
24. (b) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron 1994, 50, 1295.
25. (c) Bowman, W. R.; Clark, D. N., Marmon, R. J. Tetrahedron Lett. 1991, 32, 6441.
26. Michejda, C. J.; Campbell, D. H.; Sieh, D. H.; Koepke, S. R. In, Organic Free Radicals; Pryor, W. A., Ed.; ACS Symposium Series 69; American Chemical Society: Washington, DC, 1978; p 292.
27. This result is belived to be in error, see ref 3d.
28. Maeda, Y.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 328.
29. This value is believed to be underestimated by about a factor of 5; see: Nazran, A. S.; Griller, D. J. Am. Chem. Soc. 1983, 105, 1970.
30. This value has been recently revised to 1; see ref 3b.
31. Part of this work has appeared in preliminary form: (a) Maxwell, B. J.; Tsanaktsidis, J. J. Chem. Soc., Chem. Commun. 1994, 533. (b) Beckwith, A. L. J.; Maxwell, B. J.; Tsanaktsidis, J. Aust. J. Chem. 1991, 44, 1809.
32. Part of this work has appeared in preliminary form: (a) Maxwell, B. J.; Tsanaktsidis, J. J. Chem. Soc., Chem. Commun. 1994, 533. (b) Beckwith, A. L. J.; Maxwell, B. J.; Tsanaktsidis, J. Aust. J. Chem. 1991, 44, 1809.
33. Cf. ref 6c.
34. (a) Craine, L.; Rabin, M. Chem. Rev. 1989, 89, 589.
35. (b) Davis, F. A. Int. J. Sulfur Chem. 1973, 8, 71.
36. Allen, C. F. H.; MacKay, D. D. Organic Syntheses; Wiley: New York, 1943; Collective Vol. 2, p 580.
37. 2O; see: Szammer, J.; Ötvös, L. Chem. Ind. 1988, 754.
38. A reviewer pointed out that 2,4,6-tri-terr-butyiphenol does not trap carbon-or tin-centered radicals at significant rates and suggested that our observations may imply the generation of nitrogen-centered radicals in the control experiments.
39. Newcomb, M. Tetrahedron 1993, 49, 1151.
40. 20 potentially capable of influencing these reactions; every effort was made to minimize such impurities in these reactions.
41. Omae, I. Journal of Organometallic Chemistry Library; Organotin Chemistry, Elsevier: Amsterdam. 1989; Vol. 21, p 66.
42. 2O and 8.
43. Giese, B. Angew. Chem. Int. Ed. Engl. 1983, 22, 753
44. Michejda, C. J.; Campbell, D. H. Tetrahedron Lett. 1977, 577.
45. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Persamon Press: New York. 1992.
46. Nair, M. G.; Campbell, P. T.; Baugh, C. M. J. Org. Chem. 1975, 40, 1745.
47. Bennett, O. F.; Johnson, J.; Tramondozzi, J. Org. Prep. Proc. Int. 1974, 6, 287.