The Reaction of 1-Tetralones with Thallium Trinitrate Supported on Clay: Ring Contraction vs α-Oxidation

Journal of the Brazilian Chemical Society

Volumn 12, Issue 5, 2001, Pages 680-684

  Ferraz, Helena M C ^a   Silva Jr , Luiz F ^a   Aguilar, Andrea M ^a   Vieira, Tiago O ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Indans; Montmorillonite K 10; Ring contraction; Thallium trinitrate; oxidation

Indexed keywords

EID: 0035620963     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532001000500012     Document Type: Article

References (20)

1. Hong, B.-C.; Sarshar, S. Org. Prep. Proc. Int. 1999, 31, 1.
2. Ferraz, H. M. C.; Silva Jr, L. F. J. Org. Chem. 1998, 63, 1716.
3. (a) Ferraz, H. M. C.; Santos, A. P.; Silva Jr, L. F.; Vieira, T. O. Synth. Commun. 2000, 30, 751.
4. (b) Ferraz, H. M. C.; Silva Jr, L. F.; Vieira, T. O. Tetrahedron 2001, 57, 1709.
5. Aldrich catalog 1998/1999. 1-Tetralones are about 6 times cheaper than the corresponding 1-indanones.
6. Ferraz, H. M. C.; Vieira, T. O.; Silva Jr, L. F. Synthesis 1999, 2001.
7. Taylor, E. C.; Chiang, C.-S.; McKillop, A.; White, J. F. J. Am. Chem. Soc. 1976, 98, 6750.
8. Miles, D. H.; Lho, D.-S.; Chittawong, V.; Payne, A. M. J. Org. Chem. 1990, 55, 4034.
9. Ferraz, H. M. C.; Silva Jr, L. F. Tetrahedron Lett. 1997, 38, 1899.
10. McKillop, A.; Hunt, J. D.; Taylor, E. C. J. Org. Chem. 1972, 37, 3381.
11. Wiberg, K. B.; Koch, W. Tetrahedron Lett. 1966, 1779.
12. For a discussion concerning the mechanisms, see reference 8.
13. Ciattini, P. G.; Morera, E.; Ortar, G. J. Heterocyclic Chem. 1982, 19, 395.
14. Zubaidha, P. K.; Chavan, S. P.; Racherla, U. S.; Ayyangar, N. R. Tetrahedron 1991, 47, 5759.
15. Katritzky, A. R.; Xie, L. H.; Scrdyuk, L. J. Org. Chem. 1996, 61, 7564.
16. Arnould, J. C.; Pete, J. P. Tetrahedron 1975, 31, 815.
17. Beckwith, A. L. J.; Gerba, S. Aust. J. Chem. 1992, 45, 289.
18. Plusquellec, D.; Kerfanto, M. Tetrahedron Lett. 1974, 1495.
19. Nongrum, F. M.; Myrboh, B. Synthesis 1987, 845.
20. Pang, Y.-P.; Kozikowski, A. P. J. Org. Chem. 1991, 56, 4499.