Thallium trinitrate mediated ring contraction of trans-2-decalones: An alternative entry to the hydrindane system

Journal of Organic Chemistry

Volumn 63, Issue 5, 1998, Pages 1716-1718

  Ferraz, Helena M C ^a   Silva Jr , Luiz F ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003352404     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971585r     Document Type: Note

References (34)

1. For some recent examples of trans-hydrindanes, see: (a) Uenishi, J.; Kawahama, R.; Yonemitsu, O. J. Org. Chem. 1997, 62, 1691.
2. (b) Ishii, S.; Helquist, P. Synlett 1997, 508.
3. (c) Saha, A.; Bhattacharjya, A. J. Chem. Soc., Chem. Commun. 1997, 495.
4. (d) Batey, R. A.; Lin, D.; Wong, A.; Hayhoe, C. L. S. Tetrahedron Lett. 1997, 38, 3699.
5. For some recent examples of cis-hydrindanes, see: (a) Lee, Y.-K.; Singleton, D. A. J. Org. Chem. 1997, 62, 2255.
6. (b) Sha, C.-K.; Chiu, R.-T.; Yang, C.-F.; Yao, N.-T.; Tseng, W.-H.; Liao, F.-L.; Wang, S.-L. J. Am. Chem. Soc. 1997, 119, 4130.
7. (c) Vonwiller, S. C.; Warner, J. A.; Mann, S. T.; Haynes, R. K. Tetrahedron Lett. 1997, 38, 2363.
8. (d) Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634.
9. (e) Rönn, M.; Andersson, P. G.; Bäckvall, J.-E. Tetrahedron Lett. 1997, 38, 3603.
10. (f) Mehta, G.; Reddy, D. S. Synlett 1997, 612.
11. Ferraz, H. M. C.; Silva, L. F., Jr. Tetrahedron Lett. 1997, 38, 1899.
12. For thallium(III) salt mediated ring contraction of ketones, see: (a) Grisar, J. M.; Bolkenius, F. N.; Petty, M. A.; Verne, J. J. Med. Chem. 1995, 38, 453.
13. (b) Singh, O. V.; Khanna, M. S.; Garg, C P.; Kapoor, R. P. Synth. Commun. 1993, 23, 585.
14. (c) Mincione, E.; Bovicelli, P.; Gil, J. B.; Forcellese, M. L. Gazz. Chim. Ital. 1985, 115, 37.
15. (d) Irwin, A. J.; Jones, J. B. J. Org. Chem. 1977, 42, 2176.
16. (e) Taylor, E. C.; Chiang, C. S.; McKillop, A.; White, J. F. J. Am. Chem. Soc., 1976, 98, 6750.
17. (f) McKillop, A.; Hunt, J. D.; Taylor, E. C. J. Org. Chem. 1972, 37, 3381.
18. (g) Wiberg, K. B.; Koch, W. Tetrahedron Lett. 1966, 1779. (h) References cited in 3 and 4a-g.
19. Middleton, S.; Stock, L. E. Aust. J. Chem. 1980, 33, 2467.
20. Smissman, E. E.; Lemke, T. L.; Kristiansen, O. J. Am. Chem. Soc. 1966, 88, 334.
21. (a) Borodkin, G. I.; Panova, E. B.; Shakirov, M. M.; Shubin, V. G. J. Org. Chem. USSR 1983, 19, 103 and references therein.
22. (b) Shono, T.; Fujita, K.; Kumai, S. Tetrahedron Lett. 1973, 3123.
23. 4e
24. Mundy, B. F. J. Chem. Educ. 1972, 49, 91.
25. Heathcook, C. H.; Ellis J. E.; McMurry, J. E.; Coppolino, A. Tetrahedron Lett. 1971, 4995.
26. Still, W. C.; VanMiddlesworth, F. L. J. Org. Chem. 1977, 42, 1258.
27. Zoretic, P. A.; Golen, J. A.; Saltzman, M. D. J. Org. Chem. 1981, 46, 3554.
28. (a) House, H. O.; Giese, R. W.; Kronberger, K.; Kaplan, J. P.; Simeone J. F. J. Am. Chem. Soc. 1970, 92, 2800.
29. (b) Caine, D.; Smith, T. L., Jr. J. Org. Chem. 1978, 43, 755.
30. Stork, G.; Rosen, P.; Goldman, N.; Coombs, R. V.; Tsuji, J. J. Am. Chem. Soc. 1965, 87, 275.
31. Scanio, C. J. V.; Starrett, R. M. J. Am. Chem. Soc. 1971, 93, 1539.
32. (a) Rao, H. S. P.; Reddy, K. S. Tetrahedron Lett. 1994, 35, 171. (b) See also ref 13b.
33. Markó, I. E.; Leung, C. W. J. Am. Chem. Soc. 1994, 116, 371.
34. 3 A shorter time (24 h instead of 48 h) and a smaller amount of TTN (1.1 equiv instead of 1.5 equiv) were required to perform the reaction.