Intramolecular cyclizations via arylnitrenium ions. Formation of a six- membered ring rather than a macrocycle

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5904-5912

  Abramovitch, Rudolph A ^a   Ye, Xiaocong ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHANE; MACROCYCLIC COMPOUND; PHENANTHRENE DERIVATIVE;

ARTICLE; CYCLIZATION; MATHEMATICAL ANALYSIS; MOLECULAR INTERACTION; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033529921     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990362t     Document Type: Article

References (60)

1. (a) Evans, D. A.; Dinsmore, C. J. Tetrahedron Lett. 1993, 43, 6029.
2. (b) Itokawa, H.; Suzuki, J.; Hitoyanagi, Y.; Kondo, K.; Takaya, K Chem. Lett. 1993, 695.
3. (c) Yaa, X.-S.; Ehizuki, Y.; Noguchi, H.; Kiuchi, F.; Shibya, M.; Itaka, Y.; Seto, H.; Sankawa, U.Chem. Pharm. Bull. 1991, 39, 2956.
4. (d) Boger, D. L.; Sakuya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204,
5. (e) Whiting, D. A.; Wood, A. F. Tetrahedron Lett. 1978, 26, 2335.
6. (f) This, M. A. Chem. Rev. 1988, 88, 719.
7. (g) Fuji, K.; Ichikawa, K.; Fujita, E. J. Chem. Soc., Perkin Trans. 1 1980, 1066.
8. (a) Schubert, W. H.; Sweeney, W. A.; Latourette, H. K. J. Am. Chem. Soc. 1954, 76, 5462.
9. (b) Huisgen, R.; Rietz, U. Chem. Ber. 1957, 90, 2768.
10. (a) Walling, C. Tetrahedron 1985, 41, 3887.
11. (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
12. (a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
13. (b) Corey, E. J.; Nicolaou, K. C.; Melvin, L. S. J. Am. Chem. Soc. 1975, 97, 653, 654.
14. (c) Nicolaou, K. C. Tetrahedron 1977, 33, 683.
15. Boger, D. L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763.
16. Evans, D. A.; Ellman, J. A.; DeVries, K. M. J. Am. Chem. Soc. 1989, 111, 8912.
17. (a) Trost, B. M.; Warner, R. W. J. Am. Chem. Soc. 1982, 104, 6112.
18. (b) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943.
19. Jakeda, K.; Igaraski, Y.; Okazaki, K.; Yoshii, E.; Yamaguchi, K. J. Org. Chem. 1990, 55, 3431.
20. Stocks, M. J.; Harrison, R. P.; Teague, S. J. Tetrahedron Lett. 1995, 36, 6555.
21. Dean, F. M.; Park, B. K. J. Chem. Soc., Chem. Commun. 1975, 142.
22. Morin-Fox, M. C.; Lipton, M. A. Tetrahedron Lett. 1993, 34, 7899.
23. Fürstner, A.; Ackermann, L. J. Chem. Soc., Chem. Commun. 1999, 95.
24. Abramovitch, R. A.; Chinnasamy, P.; Evertz, K.; Huttner, G. J. Chem. Soc., Chem. Commun. 1989, 3.
25. Abramovitch, R. A.; Shi, Q. Heterocycles 1994, 38, 2347.
26. Using PC Model for Windows from Serena Software. To ensure that a global minimum energy had been reached, the various local minimum structures were altered repeatedly until the lowest energy conformation was reached consistently. Though these computations do not take into account the influence of solvent they do allow changes in the dielectric constant. The latter has been changed from 1.5 to 30.0 D without much change resulting in the global energy minimum conformations.
27. Olah, G. A.; Gupta, B. G. B.; Malhotra, R.; Narang, S. C. J. Org. Chem. 1980, 45, 1638.
28. Murray, W. V.; Hadden, S. K.; Wachter, M. P. J. Heterocycl. Chem. 1990, 27, 1933.
29. (a) Elsinger, F. Org. Synth. 1965, 45, 7.
30. (b) Johnson, F.; Paul, K. G.; Favara, D. J. Org. Chem. 1982, 47, 4254.
31. Kawaski, I.; Matsuda, K.; Kaneko, T. Bull. Chem. Soc. Jpn. 1971, 44, 1986.
32. Mackenzie, A. R.; Moody, C. J.; Rees, C. W. Tetrahedron. 1986, 42, 3259.
33. (a) Wuthrich, K. J. Biol. Chem. 1990, 265, 22059.
34. (b) Wagner, G.; Braun, W.; Havel, T. F.; Schaumann, T.; Go, N.; Wuthrich, K. J. Mol. Biol. 1987, 196, 611.
35. (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377; Synthesis 1984, 709.
36. (a) Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377; Synthesis 1984, 709.
37. (b) Moriarty, R. M.; Prakash, O. Russ. Chem. Rev. 1987, 56, 826.
38. (c) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431.
39. (d) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365.
40. (a) Koser, G. F. Hypervalent Halogen Compounds. In The Chemistry of Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U. K., 1983; Supplement D, Chapter 18, p 721.
41. (b) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publisher: New York, 1992.
42. (c) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113.
43. Szántay, C.; Blaskó, G.; Bárczai-Beke, M.; Péchy, P.; Dõrbteu, G. Tetrahedron Lett. 1980, 21, 3509.
44. Kita, Y.; Okunaka, R.; Kondo, M.; Tohma, H.; Inagaki, M.; Hatanaka, K. J. Chem. Soc., Chem. Commun. 1992, 429.
45. de Sousa, J. D. F.; Rodrigues, J. A. R.; Abramovitch, R. A. J. Am. Chem. Soc. 1994, 116, 9745.
46. Zhdankin, V. V.; Crittell, C. M.; Stang, P. J. Tetrahedron Lett. 1990, 31, 4821.
47. Yuster, Y.; Saldana, M.; Walls, F. Tetrahedron Lett. 1982, 23, 147.
48. Smith, P. A. S.; Boyer, J. H. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p75.
49. Webb, G. A. Annual Reports on NMR Spectroscopy Vol. 10B; Academic Press: New York, 1980; p 50.
50. Abramovitch, R. A.; Hawi, A.; Rodrigues, J. A. R.; Trombetta, T. R. J. Chem. Soc., Chem. Commun. 1986, 283.
51. Carreño, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urano, A. J. Org. Chem. 1995, 60, 5328.
52. (a) McOmie, J. F. W.; West, D. E. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V; 412.
53. (b) Danheiser, R. L.; Casebier, D. S.; Firooznia, F. J. Org. Chem. 1995, 60, 8341.
54. Hunter, C. A. Chem. Soc. Rev. 1994, 23, 101-109. Kim, E.-I.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11192-11193. Schladetzky, K. D.; Haque, T. S.; Gellman, S. H. J. Org. Chem. 1995, 60, 4108-4113.
55. Hunter, C. A. Chem. Soc. Rev. 1994, 23, 101-109. Kim, E.-I.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11192-11193. Schladetzky, K. D.; Haque, T. S.; Gellman, S. H. J. Org. Chem. 1995, 60, 4108-4113.
56. Hunter, C. A. Chem. Soc. Rev. 1994, 23, 101-109. Kim, E.-I.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11192-11193. Schladetzky, K. D.; Haque, T. S.; Gellman, S. H. J. Org. Chem. 1995, 60, 4108-4113.
57. Marshall, J. A.; DeHoff, B. S.; Crooks, S. L. Tetrahedron Lett. 1987, 28, 527. Marshall, J. A.; Anderson, M. W. J. Org. Chem. 1993, 58, 3912.
58. Marshall, J. A.; DeHoff, B. S.; Crooks, S. L. Tetrahedron Lett. 1987, 28, 527. Marshall, J. A.; Anderson, M. W. J. Org. Chem. 1993, 58, 3912.
59. Abramovitch, R. A. Unpublished result (1993).
60. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; revised by Furniss, B. S., Hannaford, A. J., Smith, P. W. G., Tatchell, A. R.; Longman Scientific & Technical: Essex, 1989.