5-Exo versus 6-Endo cyclization of primary aminyl radicals: An experimental and theoretical investigation

Journal of Organic Chemistry

Volumn 72, Issue 26, 2007, Pages 10231-10234

  Liu, Feng ^a   Liu, Kun ^a   Yuan, Xinting ^a   Li, Chaozhong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; REACTION KINETICS; REGIOSELECTIVITY;

CYCLIZATION RATE; ENDO CYCLIZATION;

ORGANIC COMPOUNDS;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; COMPARATIVE STUDY; CYCLIZATION; ENERGY TRANSFER;

EID: 37549042454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7015967     Document Type: Article

References (54)

1. For reviews, see: (a) Neale, R. S. Synthesis 1971, 1.
2. (b) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337.
3. (c) Esker, J.; Newcomb, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1993; Vol. 58, p 1.
4. (d) Zard, S. Z. Synlett 1996, 1148.
5. (e) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
6. (f) Stella, L. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, p 407.
7. (g) Bowman, W. R.; Bridge, C. F.; Brookes, P. J. Chem. Soc., Perkin Trans. 1 2000, 1.
8. (a) Cassayre, J.; Gagosz, F.; Zard, S. Z. Angew. Chem., Int. Ed. 2002, 41, 1783.
9. (b) Sharp, L. A.; Zard, S. M. Org. Lett. 2006, 8, 831.
10. (a) Horner, J. H.; Musa, O. M.; Bouvier, A.; Newcomb, M. J. Am. Chem. Soc. 1998, 120, 7738.
11. (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, K. W.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233.
12. (c) Gagosz, F.; Moutrille, C.; Zard, S. Z. Org. Lett. 2002, 4, 2707.
13. (d) Martinez, E., II; Newcomb, M. J. Org. Chem. 2006, 71, 557.
14. (a) Musa, O. S.; Horner, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862.
15. (b) Newcomb, M.; Musa, O. M.; Martinez, F. N.; Horner, J. H. J. Am. Chem. Soc. 1997, 119, 4569.
16. (a) Wagner, G. D.; Ruel, G.; Lusztyk, J. J. Am. Chem. Soc. 1996, 118, 13.
17. (b) Maxwell, B. J.; Tsanaktsidis, J. J. Am. Chem. Soc. 1996, 118, 4276.
18. (c) Maxwell, B. J.; Smith, B. J.; Tsanaktsidis, J. J. Chem. Soc., Perkin Trans. 2 2000, 425.
19. (a) Horner, J. H.; Martinez, F. N.; Musa, O. M.; Newcomb, M.; Shahin, H. E. J. Am. Chem. Soc. 1995, 117, 11124.
20. (b) Ha, C.; Musa, O. M.; Martinez, F. N.; Newcomb, M. J. Org. Chem. 1997, 62, 2704.
21. For recent examples, see: (a) Sjoholm, A.; Hemmerling, M.; Pradeille, N.; Somfai, P. J. Chem. Soc., Perkin Trans. 1 2001, 891.
22. (b) Hasegawa, H.; Senboku, H.; Kajizuka, Y.; Orito, K.; Tokuda, M. Tetrahedron 2003, 59, 827.
23. (c) Benati, L.; Bencivenni, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Scialpi, R.; Spagnolo, P.; Zanardi, G.; Rizzoli, C. Org. Lett. 2004, 6, 417.
24. (d) Benati, L.; Bencivenni, G.; Leardini, R.; Nanni, D.; Minozzi, M.; Spagnolo, P.; Scialpi, R.; Zanardi, G. Org. Lett. 2006, 8, 2499.
25. (a) Bowman, W. R.; Coghlan, D. R.; Shah, H. C. R. Chim. 2001, 4, 625.
26. (b) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron 1994, 50, 1275.
27. (c) Guindon, Y.; Guerin, B.; Landry, S. R. Org. Lett. 2001, 3, 2293.
28. (a) Tang, Y.; Li, C. Org. Lett. 2004, 6, 3229.
29. (b) Chen, Q.; Shen, M.; Tang, Y.; Li, C. Org. Lett. 2005, 7, 1625.
30. (c) Lu, H.; Li, C. Tetrahedron Lett. 2005, 46, 5983.
31. (d) Hu, T.; Shen, M.; Chen, Q.; Li, C. Org. Lett. 2006, 8, 2647.
32. (e) Tang, Y.; Li, C. Tetrahedron Lett. 2006, 47, 3823.
33. (f) Lu, H.; Chen, Q.; Li, C. J. Org. Chem. 2007, 72, 2564.
34. Newcomb, M.; Deeb, T. M.; Marquardt, D. J. Tetrahedron 1990, 46, 2317.
35. Newcomb, M.; Weber, K. A. J. Org. Chem. 1991, 56, 1309.
36. (a) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron Lett. 1991, 32, 6441.
37. (b) Beckwith, A. L. J.; Maxwell, B. J.; Tsanakatsidis, J. Aust. J. Chem. 1991, 44, 1809.
38. (c) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron Lett. 1992, 33, 4993.
39. (d) Maxwell, B. J.; Tsanaktsidis, J. J. Chem. Soc., Chem. Commun. 1994, 533.
40. Behforouz, M.; Kerwood, J. E. J. Org. Chem. 1969, 34, 51.
41. Hartung, J.; Kneuer, R.; Rummey, C.; Bringmann, G. J. Am. Chem. Soc. 2004, 126, 12121.
42. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
43. For review articles on use of calculations in radical reactions, see: (a) Eksterowicz, J. E.; Houk, K. N. Chem. Rev. 1993, 93, 2439.
44. (b) Schiesser, C. H.; Skidmore, M. A. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, p 337.
45. For the recent selected examples, see: (a) Itoh, Y.; Houk, K. N.; Mikami, K. J. Org. Chem. 2006, 71, 8918.
46. (b) O'Neil, L. L.; Wiest, O. J. Org. Chem. 2006, 71, 8926.
47. (c) Hartung, J.; Daniel, K.; Rummey, C.; Bringmann, G. Org. Biomol. Chem. 2006, 4, 4089.
48. (d) Lin, H.; Chen, Q.; Cao, L.; Yang, L.; Wu, Y.-D.; Li, C. J. Org. Chem. 2006, 71, 3328.
49. (e) Liu, L.; Chen, Q.; Wu, Y.-D.; Li, C. J. Org. Chem. 2005, 70, 1539.
50. (f) Speybroeck, V. V.; De Kimpe, N.; Waroquier, M. J. Org. Chem. 2005, 70, 3674.
51. (g) References 9d and 9f.
52. Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A 2001, 105, 6750.
53. Kazuaki, I.; Takayuki, Y. Org. Lett. 2004, 6, 1983.
54. Albert, P.; David, J. A.; Alan, T. P., David, W. M. Tetrahedron 1996, 52, 3247.