Tandem 1,3-dipolar cycloaddition of mesoionic 2,4-diphenyl-1,3- oxathiolium-5-olate with cycloocta-1,5-diene. A new synthesis of the tetracyclo[6.2.0.04,10.05,9]decane ring system

Tetrahedron Letters

Volumn 41, Issue 11, 2000, Pages 1687-1690

  Sponholtz Iii, William R ^a   Trujillo, Hernando A ^a   Gribble, Gordon W ^a  

^a Dartmouth College   (United States)

Author keywords

1,3 dipolar cycloaddition; 1,3 oxathiolium 5 olate; Mesoionic; Tetracyclo 6.2.0.04,10.05,9 decane

Indexed keywords

2,4 DIPHENYL 1,3 OXAATHIOLIUM 5 OLATE; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; OXIDATION; PHOTOCHEMISTRY; PHOTOOXIDATION; SYNTHESIS;

EID: 0034635798     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00042-3     Document Type: Article

References (43)

1. For outstanding reviews of the earlier literature on mesoionic heterocycles, see: (a) Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1-122.
2. For outstanding reviews of the earlier literature on mesoionic heterocycles, see: (a) Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1-122.
3. (c) Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. Tetrahedron 1985, 41, 2239-2329.
4. (a) Potts, K. T. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 2, pp. 1-82.
5. (b) Gingrich, H. L.; Baum, J. S. In The Chemistry of Heterocyclic Compounds; Turchi, I. J., Ed.; John Wiley & Sons, Inc.: New York, 1986; Vol. 45, pp. 731-961.
6. (c) Padwa, A. Acc. Chem. Res. 1991, 24, 22-28.
7. (d) Padwa, A.; Hornbuckle, S. Chem. Rev. 1991, 91, 263-309.
8. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385-5453.
9. (f) Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123-141.
10. (g) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797-1815.
11. (h) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223-269.
12. (i) Broggini, G.; Zecchi, G. Synthesis 1999, 905-917.
13. For some recent examples of 1,3-dipolar cycloaddition reactions of mesoionic heterocycles, see: (a) Padwa, A.; Brodney, M. A.; Marino Jr., J. P.; Sheehan, S. M. J. Org. Chem. 1997, 62, 78-87.
14. (b) Padwa, A.; Sheehan, S. M. J. Org. Chem. 1997, 62, 438-439.
15. (c) Dumitrascu, F.; Draghici, C.; Dumitrescu, D.; Tarko, L.; Raileanu, D. Liebigs Ann./Recueil 1997, 2613-2616.
16. (d) Coppola, B. P.; Noe, M. C.; Hong, S. S.-K. Tetrahedron Lett. 1997, 38, 7159-7162.
17. (e) Granier, T.; Gaiser, F.; Hintermann, L.; Vasella, A. Helv. Chim. Acta 1997, 80, 1443-1456.
18. (f) Kato, H.; Kobayashi, T.; Ciobanu, M.; Kakehi, A. Tetrahedron 1997, 53, 7777-7794.
19. (h) Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982-991.
20. (i) Heidelbaugh, T. M.; Liu, B.; Padwa, A. Tetrahedron Lett. 1998, 39, 4757-4760.
21. (j) Sheehan, S. M.; Beall, L. S.; Padwa, A. Tetrahedron Lett. 1998, 39, 4761-4764.
22. (k) Clerici, F.; Gelmi, M. L.; Trimarco, P. Tetrahedron 1998, 54, 5763-5774.
23. (l) Padwa, A.; Harring, S. R.; Semones, M. A. J. Org. Chem. 1998, 63, 44-54.
24. (m) Padwa, A.; Price, A. T. J. Org. Chem. 1998, 63, 556-565.
25. (n) Straub, C. S.; Padwa, A. Org. Lett. 1999, 1, 83-85.
26. (o) Pinho e Melo, T. M. V. D.; Barbosa, D. M.; Ramos, P. J. R. S.; Rocha Gonsalves, A. M. d'A.; Gilchrist, T. L.; Beja, A. M.; Paixao, J. A.; Silva, M. R.; Alte da Veiga, L. J. Chem. Soc., Perkin Trans. 1 1999, 1219-1223.
27. (a) Gribble, G. W.; Hirth, B. H. J. Heterocycl. Chem. 1996, 33, 719-726.
28. (b) Gribble, G. W.; Sponholtz III, W. R.; Switzer, F. L.; D'Amato, F. J.; Byrn, M. P. Chem. Commun. 1997, 993-994.
29. (a) Gribble, G. W.; Pelkey, E. T.; Switzer, F. L. Synlett 1998, 1061-1062.
30. (b) Gribble, G. W.; Pelkey, E. T.; Simon, W. M.; Trujillo, H. A. submitted for publication in Tetrahedron.
31. (a) Potts, K. T.; Chen, S. J.; Kane, J.; Marshall, J. L. J. Org. Chem. 1977, 42, 1633-1638.
32. (b) Masuda, K.; Adachi, J.; Nomura, K. Chem. Pharm. Bull. 1977, 25, 1471-1473.
33. (c) Potts, K. T.; Kane, J.; Carnahan, E.; Singh, U. P. J. Chem. Soc., Chem. Commun. 1975, 417-418.
34. 22S: C, 82.97; H, 6.96; S, 10.07. Found: C, 82.74; H, 7.02; S, 10.16.
35. Although an X-ray crystal structure determination indicated the correctness of 7, the crystals were insidiously twinned and an R value that was acceptable for publication could not be obtained (unpublished results with Dr. Marianne P. Byrn).
36. (a) Cava, M. P.; Schlessinger, R. H.; Van Meter, J. P. J. Am. Chem. Soc. 1964, 86, 3173-3174.
37. (b) Cava, M. P.; Schlessinger, R. H. Tetrahedron 1965, 21, 3073-3081.
38. (c) For a review, see: Givens, R. S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker, Inc.: New York, 1981; Vol. 5, p. 227.
39. Paquette, L. A.; Fischer, J. W.; Browne, A. R.; Doecke, C. W. J. Am. Chem. Soc. 1985, 107, 686-691.
40. 2S: C, 75.40; H, 6.33; S, 9.15. Found: C, 75.12; H, 6.28; S, 8.88.
41. 2 from 8 when photolyzed in benzene solution.
42. 3) δ 142.7, 128.1, 126.7, 125.6, 61.3, 44.8, 27.3.
43. Kubota, T.; Sakurai, H. J. Org. Chem. 1973, 38, 1762-1763.