The synthesis of bicyclic ortho-quinodimethanes from tricyclic sulfones

Tetrahedron

Volumn 53, Issue 47, 1997, Pages 15957-15968

  Connolly, Terrence J ^a   Durst, Tony ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLIC 1,2 QUINODIMETHANE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0030720788     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10066-7     Document Type: Article

References (25)

1. Cava, M. P.; Nappier, D. R. J. Am. Chem. Soc. 1956, 78, 500.
2. Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873.
3. Martin, N.; Seoane, C.; Hanack, H. Org. Prep. Proc. Int. 1991, 23, 237.
4. Crew, A. P. A.; Jenkins, G.; Storr, R. C.; Yelland, M. Tetrahedron Lett. 1990, 31, 1491.
5. Chaloner, L. M.; Crew, A. P. A.; Storr, R. C.; Yelland, M. Tetrahedron Lett. 1991, 32, 7609.
6. Chaloner, L. M.; Crew, A. P. A.; O'Neill, P. M.; Storr, R. C.; Yelland, M. Tetrahedron 1992, 48, 8101.
7. Tome, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron Lett. 1993, 34, 6639.
8. Tome, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735.
9. White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117.
10. Chou, T.-S.; Chen, H.-C; Tsai, C.-Y. J. Org. Chem. 1994, 59, 2241.
11. White, L. A.; O'Neill, P. M.; Park, B. K.; Storr, R. C. Tetrahedron Lett. 1995, 36, 5983.
12. Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189.
13. Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681.
14. Haber, M.; Pindur, U. Tetrahedron 1991, 47, 1925.
15. Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242.
16. We have invoked the same type of elimination to describe the formation of several products resulting from the metal hydride mediated reduction of 3-Alkylthio-2-oxindoles. Connolly, T.J.; Durst, T. Can. J. Chem. 1997, 75, 536; Can. J. Chem. 1997, 75, 542.
17. We have invoked the same type of elimination to describe the formation of several products resulting from the metal hydride mediated reduction of 3-Alkylthio-2-oxindoles. Connolly, T.J.; Durst, T. Can. J. Chem. 1997, 75, 536; Can. J. Chem. 1997, 75, 542.
18. Meyer, N.; Seebach, D. Chem. Ber. 1980, 113, 1304.
19. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
20. Clark, M.; Crammer, R. D., III; van Opdensch, N. J. Computational Chem. 1989, 10, 982.
21. Rapoport, H.; Pasky, J. Z. J. Am. Chem. Soc. 1956, 78, 3788.
22. Panetta, C. A.; Dixit, A. S. Synthesis 1981, 59.
23. Connolly, T.J. Unpublished results.
24. See accompanying paper.
25. Ponticello, G. S.; Baldwin, J. J. J. Org. Chem. 1979, 44, 4003.