Preparation of 3-trifluoromethyl-2-cycloalkenones by the oxidative rearrangement of trifluoromethylated tertiary allylic alcohols with pyridinium chlorochromate

Journal of Fluorine Chemistry

Volumn 101, Issue 2, 2000, Pages 199-202

  Prakash, G K Surya ^a   Tongco, Emily C ^a   Mathew, Thomas ^a   Vankar, Yashwant D ^a,b   Olah, George A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

3 trifluoromethyl 2 cycloalkenones; Pyridinium chlorochromate; Trifluoromethylated tertiary allylic alcohols; Trifluoromethyltrimethylsilane

Indexed keywords

EID: 0000474637     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(99)00159-1     Document Type: Article

References (29)

1. J.T. Welch, S. Eshwarakrishnan (Eds.), Fluorine in Bioorganic Chemistry, Wiley, New York, 1991.
2. J.F. Liebman, J.A. Greenberg, W.R. Dolbier, Jr. (Eds.), Fluorine-containing Molecules. Structure, Reactivity, Synthesis, and Applications, VCH, New York, 1988.
3. R. Filler, Y. Kobayashi (Eds.), Biomedical Aspects of Organofluorine Chemistry, Elsevier, Amsterdam, 1983.
4. F.A. Smith, Handbook of Experimental Pharmacology, vol. XX, part 2, Springer, Berlin, 1970, p. 166.
5. R.E. Banks (Ed.), Organofluorine Compounds and Their Industrial Applications, Ellis Horwood, Chichester, UK, 1979.
6. Prakash G.K.S., Yudin A. Chem. Rev. 97:1997;757.
7. E.C. Tongco, G.K.S. Prakash, G.A. Olah, Synlett (1997) 1193.
8. Weidemann J., Heiner T., Mloston G., Prakash G.K.S., Olah G.A. Angew. Chem. Int. Ed. Engl. 37:1998;820.
9. Y. Yamada, H. Uda, K. Nakanishi, J. Chem. Soc., Chem. Commun. (1966) 423.
10. Trost B.M. Angew. Chem. Int. Ed. Engl. 25:1986;1.
11. Trost B.M. Pure Appl. Chem. 60:1988;1615.
12. Dauben W.G., Michno D.M. J. Org. Chem. 42:1977;682.
13. Babler J.H., Coghlin M.J. Synth. Commun. 6:1976;469.
14. Sundararaman P., Herz W. J. Org. Chem. 42:1977;813.
15. Luzzio F.A., Moore W.J. J. Org. Chem. 58:1993;2966 and references cited therein.
16. D. Liotta, D. Brown, W. Hoekstra, R. Monihan, Tetrahedron Lett. (1987) 1069.
17. G. Majetich, S. Condon, K. Hull, S. Ahmad, Tetrahedron Lett. (1989) 1033.
18. Wada E., Okawara M., Nakai T. J. Org. Chem. 44:1979;2952.
19. E. Öhler, E. Zbiral, Synthesis (1991) 357.
20. P.S. Brown, A.B. McElroy, S. Warren, Tetrahedron Lett. (1985) 249.
21. A.B. McElroy, S. Warren, Tetrahedron Lett. (1985) 1677.
22. E.J. Corey, J.W. Suggs, Tetrahedron Lett. (1975) 2647.
23. E.J. Corey, G. Schmidt, Tetrahedron Lett. (1979) 399.
24. J.C. Collins, W.W. Hess, F.J. Frank, Tetrahedron Lett. (1968) 3363.
25. R.G. Curtis, I. Heilbron, E.R.H. Jones, G.F. Woods, J. Chem. Soc. (1953) 457.
26. Y. Cheng, W. Liu, S. Chen, Synthesis (1980) 223.
27. Luzzio F.A., Adams L.L. J. Org. Chem. 54:1989;5387.
28. G.A. Olah, P.S. Iyer, G.K.S. Prakash, Synthesis (1986) 513.
29. M. Hachoumy, T. Mathew, E.C. Tongco, Y.D. Vankar, G.K.S. Prakash, G.A. Olah, Synlett. (1999) 363.