Synthesis of bridgehead nitrogen heterocycles via cyclization of α- ammonio 5-hexenyl radicals

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 1798-1806

  Della, Ernest W ^a   Smith, Paul A ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; HEPTANE; INORGANIC SALT; METHYL GROUP; NITROGEN; OXIDE; PIPERIDONE DERIVATIVE; RADICAL; TIN; TRIBUTYLTIN;

ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMODYNAMICS;

EID: 0033583272     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9813538     Document Type: Article

References (51)

1. Rawal, V. H.; Singh, S. P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718 and references therein.
2. Journet, M., Malacria, M. J. Org. Chem. 1992, 57, 3085. Agnel, G.; Malacria, M. Synthesis 1989, 687.
3. Journet, M., Malacria, M. J. Org. Chem. 1992, 57, 3085. Agnel, G.; Malacria, M. Synthesis 1989, 687.
4. Baban, J. A.; Marti, V. P. J.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1985, 1723.
5. Nimmesgern, H.; Padwa, A.; Wong, G. K. S. Tetrahedron Lett. 1985, 26, 957. Nimmesgern, H.; Padwa, A.; Wong, G. K. S. J. Org. Chem. 1985, 50, 5620.
6. Nimmesgern, H.; Padwa, A.; Wong, G. K. S. Tetrahedron Lett. 1985, 26, 957. Nimmesgern, H.; Padwa, A.; Wong, G. K. S. J. Org. Chem. 1985, 50, 5620.
7. For leading references, see: (a) Brocks, J. J.; Beckhaus, H.-D.; Beckwith, A. L. J.; Rüchardt, C. J. Org. Chem. 1998, 63, 1935.
8. (b) Jurisic, B. S.; Timberlake, J. W.; Engel, P. S. Tetrahedron Lett. 1996, 37, 6473.
9. (c) Gauld, J. W.; Radom, L. J. Phys. Chem. 1994, 98, 777.
10. (d) Bordwell, F. G.; Zhang, X.-M.; Alnajjar, M. S. J. Am. Chem. Soc. 1992, 114, 7623.
11. (e) Coolidge, M. B.; Borden, W. T. J. Am. Chem. Soc. 1988, 110, 2298.
12. (f) Pasto, D. J.; Krasnansky, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062.
13. (a) Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1996; Vol. 48, p 301, Chapter 2, 1996.
14. (b) For an extensive review on radicals in natural product synthesis, see: Curran, D. P.; Fevig, T. L.; Jasperse, C. P. Chem. Rev. 1991, 91, 1237.
15. (c) Curran, D. P. Synlett 1991, 63.
16. (d) Radikale, C. In Methoden der Organischen Chimie; Regitz, M., Giese, B., Eds.; Houben-Weyl: Stuttgart, 1989; Band E 19a.
17. (e) Curran, D. P. Synthesis 1988, 417 (Part 1), 489 (Part 2).
18. (f) Newman, W. P. Synthesis 1987, 665.
19. (g) Ramaiah, M. Tetrahedron 1987, 43, 3541.
20. (h) Giese, B. In Radicals in Organic Synthesis: Formation of Carbon Carbon Bonds; Baldwin, J. E., Ed.; Pergamon: New York, 1986.
21. (i) Hart, D. J. Science 1984, 223, 883.
22. (j) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, p 162.
23. Della, E. W.; Elsey, G. M. Unpublished observations.
24. Della, E. W.; Knill, A. M.; Smith, P. A. J. Chem. Soc., Chem. Commun., 1996, 1637.
25. Bertrand, M. P.; Gastaldi, S.; Nouguier, R. Synlett 1997, 1420.
26. Rios, L. A.; Dolbier, W. R.; Paredes, R.; Lusztyk, J.; Ingold, K. U.; Jonsson, M. J. Am. Chem. Soc. 1996, 118, 11313.
27. Anderson, N. H.; Norman, R. O. C. J. Chem. Soc. B 1971, 993.
28. Bonazzola, L.; Iacona, C.; Michaut, J. P.; Roncin, J. J. Chem. Phys. 1980, 73, 4175.
29. Bonazzola, L.; LeRay, N.; Ellinger, Y. Chem. Phys. 1982, 73, 145.
30. Bouma, W. J.; Dawes, J.; M. Radom, L. Org. Mass. Spectrom. 1983, 18, 12.
31. Della, E. W.; Knill, A. M. J. Org. Chem. 1996, 61, 7529.
32. Beckwith, A. L. J.; Pigou, P. E. Aust. J. Chem. 1986, 39, 77.
33. Ho, T. L. Synthesis, 1972, 702.
34. Hawthorne, D. G.; Johns, S. R.; Willing, R. I. Aust. J. Chem. 1976, 29, 315.
35. For leading references, see: Boelsterli, J.; Eggnauer, U.; Pombo-Villar, E.; Weber, H.-P.; Walkinshaw, M.; Gould, R. O. Helv. Chim. Acta 1992, 75, 507-512 and ref 2a-k cited therein. Cottrell, I. F.; Hands, D.; Kennedy, D. J.; Paul, K. J.; Wright. S. H. B.; Hoogsteen, K. J. Chem. Soc., Perkin Trans. 1 1991, 1091-1097 and refs 1-3 cited therein.
36. For leading references, see: Boelsterli, J.; Eggnauer, U.; Pombo-Villar, E.; Weber, H.-P.; Walkinshaw, M.; Gould, R. O. Helv. Chim. Acta 1992, 75, 507-512 and ref 2a-k cited therein. Cottrell, I. F.; Hands, D.; Kennedy, D. J.; Paul, K. J.; Wright. S. H. B.; Hoogsteen, K. J. Chem. Soc., Perkin Trans. 1 1991, 1091-1097 and refs 1-3 cited therein.
37. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833.
38. McElvain, S. M.; McMahon, R. E. J. Org. Chem. 1949, 14, 1.
39. Pietraszkiewicz, M.; Salanski, P.; Jurczak, J. J. Chem. Soc. Chem. Commun. 1983, 1184.
40. (a) Reich, H. J.; Cohen, M. L. J. Org. Chem. 1979, 44, 3148.
41. (b) Simanek, V.; Klasek, A. Tetrahedron Lett. 1969, 35, 3039.
42. (a) Shamma, M.; Deno, N. C.; Remar, J. F. Tetrahedron Lett. 1966, 1375.
43. (b) Kametani, T., Kigasawa, K; Hiiragi, M.; Wagatsuma, N.; Wakisaka, K. Tetrahedron Lett. 1969, 635.
44. (a) Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288.
45. (b) Ouyang, X.; Armstrong, R. W.; Murphy, M. M. J. Org. Chem. 1998, 63, 1027.
46. Kinnel, R. B.; Molloy, B. B.; Graham, D. W.; Harding, K. E. Org. Prep. Proced. Int. 1972, 4, 27.
47. Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195.
48. Clark, R. J. H.; Stockwell, J. A. J. Chem. Soc., Dalton Trans. 1975, 468.
49. Campbell, K. N.; Fatora, F. C.; Campbell, B. K. J. Org. Chem. 1952, 17, 1141.
50. Collins, C. J.; Hanack, M.; Stutz, H.; Auchter, G.; Schoberth W. J. Org. Chem. 1983, 48, 5265.
51. Kosolapoff, G. M. J. Org. Chem. 1946, 11, 3.