Bu3SnH mediated oxidative radical cyclisations: Synthesis of 6H-benzo[c]chromen-6-ones

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 17, 2000, Pages 2991-2999

  Bowman, W Russell ^a   Mann, Emma ^a   Parr, Jonathan ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ISOMERS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SYNTHESIS (CHEMICAL);

OXIDATIVE RADICAL CYCLIZATIONS;

AROMATIC HYDROCARBONS;

EID: 0034618929     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002539i     Document Type: Article

References (51)

1. F. Aldabbagh, W. R. Bowman, Contemp. Org. Synth., 1997, 4, 261;
2. Th. Kappe and C. O. Kappe, in Progress in Heterocyclic Chemistry, eds. H. Suschitzky and G. Gribble, Elsevier Science, New York, 1996, vol. 8;
3. W. R. Bowman, C. F. Bridge and P. Brookes, J. Chem. Soc., Perkin Trans. 1, 2000, 1;
4. A. G. Fallis and I. M. Brina, Tetrahedron, 1997, 53, 17543;
5. T. Naito, Heterocyclcs, 1999, 50, 505;
6. L. Yet, Tetrahedron, 1999, 55, 9349.
7. W. R. Bowman, H. Heaney and B. M. Jordan, Tetrahedron, 1991, 47, 10119.
8. A. M. Rosa, A. M. Lobo, P. S. Branco, S. Prabhakar and A. M. D. L. Pereira, Tetrahedron, 1997, 53, 269.
9. A. M. Rosa, A. M. Lobo, P. S. Branco and S. Prabhakar, Tetrahedron, 1997, 53, 285.
10. A. M. Rosa, A. M. Lobo, P. S. Branco, S. Prabhakar and M. Sá-da-Costa, Tetrahedron, 1997, 53, 299;
11. C. Tsuge, T. Halta and H. Tsuchiyama, Chem. Lett., 1998, 155;
12. M. L. E. N. da Mata, W. B. Motherwell and F. Ujjainwalla, Tetrahedron Lett., 1997, 38, 137, 141;
13. W. B. Motherwell, A. M. K. Pennell and F. Ujjainwalla, J. Chem. Soc., Chem. Commun., 1992, 1067;
14. W. B. Motherwell and A. M. K. Pennell, J. Chem. Soc., Chem. Commun., 1991, 877.
15. D. Crich and J.-T. Hwang, J. Org. Chem., 1998, 63, 2765.
16. T. Nakanishi, M. Suzuki, A. Mashiba, K. Ishikawa and T. Yokotsuka, J. Org. Chem., 1998, 63, 4235.
17. F. Aldabbagh, W. R. Bowman, E. Mann and A. M. Z. Slawin, Tetrahedron, 1999, 55, 8111.
18. F. Aldabbagh and W. R. Bowman, Tetrahedron, 1999, 55, 4109.
19. T. C. T. Ho and K. Jones, Tetrahedron, 1997, 53, 8287.
20. Y. Antonio, M. A. E. De La Cruz, E. Galeazzi, A. Guzman, B. L. Bray, R. Greenhouse, L. J. Kurz, D. A. Lustig, M. L. Maddox and J. M. Muchowski, Can. J. Chem., 1994, 72, 15.
21. F. E. Ziegler and M. Belema, J. Org. Chem., 1997, 62, 1083 and references therein;
22. C. J. Moody and C. L. Norton, J. Chem. Soc., Perkin Trans. 1, 1997, 2639.
23. A. Padwa, M. Dimitroff, A. G. Waterson and T. Wu, J. Org. Chem., 1998, 63, 3986.
24. J . A. Murphy and M. S. Sherburn, Tetrahedron, 1991, 47, 4077; and references therein.
25. D. J. Hagan, E. Giménez-Arnau, C. H. Schwalbe and M. F. G. Stevens, J. Chem. Soc., Perkin Trans. 1, 1997, 2739.
26. A. Nadin and T. Harrison, Tetrahedron Lett., 1999, 40, 4073.
27. D. C. Harrowven and M. I. T. Nunn, Tetrahedron Lett., 1998, 39, 5875.
28. H. Josien, S.-B. Ko, D. Bom and D. P. Curran, Chem. Eur. J., 1998, 4, 70; and references therein.
29. D. P. Curran and H. Liu, J. Chem. Soc., Perkin Trans. 1., 1994, 1377.
30. A. L. J. Beckwith and J. M. D. Storey, J. Chem. Soc., Chem. Commun., 1995, 977.
31. Leading references: P. Phillips, Chem. Br., 1997, 32;
32. S. Ghosal, Pure Appl. Chem., 1990, 62, 1285;
33. S. Ghosal, J. Lal, S. K. Singh, Y. Kumar and F. Doti, J. Chem. Res. (S), 1989, 350;
34. S. Ghosal, S. K. Singh and R. S. Srivatava, J. Chem. Res. (S), 1988, 196.
35. A. J. Kirby, Stercoelectronic Effects, Oxford University Press, Oxford, 1996, pp. 22-24.
36. Some leading references: D. L. J. Clive and P. L. Beaulieu, J. Chem. Soc., Chem. Commun., 1983, 307;
37. D. P. Curran and J. Tamine, J. Org. Chem., 1991, 56, 2746;
38. V. H. Rawal, S. P. Singh, C. Dufour and C. Michoud, J. Org. Chem., 1991, 56, 5245;
39. R. Nougier, S. Gastaldi, D. Stein, M. Bertrand and P. Renaud, Tetrahedron Lett., 1999, 40, 3371;
40. A. L. J. Beckwith and P. E. Pigou, J. Chem. Soc., Chem. Commun., 1986, 85.
41. A. L. J. Beckwith and J. M. D. Storey, Australian National University, Canberra, unpublished results.
42. C. Wang, G. A. Russell and W. S. Trahanovsky, J. Org. Chem., 1998, 63, 9956; and references therein.
43. A. E. Lakach, A. N. Santiago and R. A. Rossi, J. Phys. Org. Chem., 1994, 7, 610; and references therein.
44. D. P. Curran, H. Yu and H. Lie, Tetrahedron, 1994, 50, 7343.
45. P. S. Engel and W.-X. Wu, J. Am. Chem. Soc., 1989, 111, 1830.
46. I. P. Beletskaya, A. S. Sigeev, V. A. Kuzman, A. S. Tatikolov and L. Hevesi, J. Chem. Soc., Perkin Trans. 2, 2000, 107.
47. W. K. Busfield, I. D. Jenkins and P. Van Le, Polym. Bull., 1997, 38, 149.
48. J. Clayden, J. J. A. Cooney and M. Julia, J. Chem. Soc., Perkin Trans. 1, 1995, 7.
49. C. G. Huang and P. Wan, J. Org. Chem., 1991, 56, 4846.
50. D. D. Hennings, S. Iwasa and V. H. Rawal, J. Org. Chem., 1997, 62, 2.
51. G. W. K. Cavill, F. M. Dean, J. F. E. Keenan, A. McGookin, A. Robertson and G. B. Smith, J. Chem. Soc., 1958, 1544.