An efficient dehyrohalogenation method for the synthesis of α,β,β-trifluorostyrenes, α-chloro-β,β- difluorostyrenes and E-1-arylperfluoroalkenes

Journal of Fluorine Chemistry

Volumn 126, Issue 8, 2005, Pages 1174-1184

  Anilkumar, R ^a   Burton, Donald J ^a  

^a E11 SSH   (United States)

Author keywords

1,2,2 Trifluorostyrene; 1 Aryl 1,2,2,2 tetrafluoroethane; 1 Arylperfluoroalkene; 1 Chloro 1 aryl 2,2,2 trifluoroethane; 1 Chloro 2,2 difluorostyrene; DAST; Dehydrofluorination; Dehydrohalogenation; LHMDS; Trifluoromethylketone

Indexed keywords

EID: 23044516673     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2005.05.005     Document Type: Article

References (44)

1. T. Fuchikami Yuki Gosei Kagaku Kyokai Shi 42 1984 775 785
2. Y. Takeuchi Yuki Gosei Kagaku Kyokai Shi 46 1988 145 159
3. M. Shimizu, and T. Hiyama Angew. Chem. Int. Ed. 44 2005 214 231
4. J.T. Welch Tetrahedron 43 1987 3123 3197
5. W.B. Motherwell, and B.C. Tozer J. Chem. Soc. Chem. Commun. 1989 1437 1439
6. P.M. Weintraub, A.K. Holland, C.A. Gates, W.R. Moore, R.J. Resvick, P. Bey, and N.P. Peet Bioorg. Med. Chem. 11 2003 427 431
7. I.A. McDonald, M.J. Lacoste, P. Bey, M.G. Palfreyman, and M. Ziena J. Med. Chem. 28 1985 186 193
8. J.R. McCarthy, D.P. Mathews, D.M. Stemerick, E.W. Huber, P. Bey, B.J. Lippert, R.D. Snyder, and P.S. Sunkara J. Am. Chem. Soc. 112 1991 7439 7440
9. M. Fujita, and T. Hiyama Yuki Gosei Kagaku Kyokai Shi. 45 1987 664 671
10. D.R. James, US Patent, 4,335,137, Chem. Abstr. 97 (1982) 140228c.
11. P. Massardo, G. Bettarini, G. Giovarruscio, P. Piccardi, F. Reggiori, V. Caprioli, EP 123,302, Chem. Abstr. 102 (1985) 95427f.
12. P. Massardo, F. Rama, P. Piccardi, V. Caprioli, EP 123,302, Chem. Abstr. 106 (1987) 196060u.
13. T.S. Nikitina Russ. Chem. Rev. 59 1990 575 589
14. T. Narita, T. Hagiwara, H. Hamana, K. Shibasaki, and I. Hiruta J. Fluorine Chem. 71 1995 151 153
15. T. Aoki, J. Watanabe, Y. Ishimoto, E. Oikawa, Y. Hayakawa, and M. Nishida J. Fluorine Chem. 59 1992 285 288
16. C. Stone, T.S. Daynard, L.-Q. Hu, C. Mah, and A.E. Steck J. New Mater. Electrochem. Syst. 3 2000 43 50
17. C. Stone, A.E. Steck, PCT Int. Appl. WO 2001058576.
18. T. Momose, T. Kitazumi, I. Ishigaki, and J. Okamoto J. Appl. Polym. Sci. 39 1990 1221 1230
19. R. Wodzki, A. Narebska, and J. Ceynowa Angew. Makromol. Chem. 106 1982 23 35
20. R. Anilkumar, and D.J. Burton Tetrahedron Lett. 43 2002 2731 2733
21. A. Raghavanpillai, and D.J. Burton J. Org. Chem. 69 2004 7083 7091
22. R. Anilkumar, and D.J. Burton Tetrahedron Lett. 43 2002 6979 6982
23. R. Anilkumar, and D.J. Burton J. Fluorine Chem. 125 2004 561 566
24. R. Anilkumar, and D.J. Burton J. Fluorine Chem. 126 2005 457 463 835-843
25. R. Anilkumar, and D.J. Burton Tetrahedron Lett. 44 2003 6661 6664
26. W.J. Middleton J. Org. Chem. 40 1975 574 578
27. K.T. Dishart, and R. Levine J. Am. Chem. Soc. 78 1956 2268 2270
28. X. Creary J. Org. Chem. 52 1987 5026 5030
29. R. Stewart, and K.C. Teo Can. J. Chem. 58 1980 2491 2496
30. K. Ramesh, D.R. Bellew, and S.G.K. Prakash J. Org. Chem. 56 1991 984 989
31. P.L. Heinze, and D.J. Burton J. Org. Chem. 53 1988 2714 2720
32. D.J. Burton J. Fluorine Chem. 23 1983 339 357
33. I. Tellier, R. Sauvetre, and J.F. Normant J. Organomet. Chem. 303 1986 309 315
34. D.J. Burton, A.L. Anderson, R. Takei, H.F. Koch, and T.L.R. Shih J. Fluorine Chem. 16 1980 229 235
35. R. Fuchs, and J.G. Park J. Am. Chem. Soc. 79 1957 993 994
36. J.T. Welch, and S. Esawakrishnan Fluorine in Bioorganic Chemistry 1991 Wiley New York
37. M. Kuroboshi, and T. Hiyama Chem. Lett. 1990 1607 1610
38. M. Kuroboshi, N. Yamada, Y. Takebe, and T. Hiyama Tetrahedron Lett. 36 1995 6271 6274
39. D.J. Burton, and J.A. Headley J. Fluorine Chem. 18 1981 323 356
40. R.N. Haszeldine, A.J. Mitchinson, R. Rowland, and A.E. Tipping J. Chem. Soc. Perkin. Trans. 1 1976 517 525
41. P. Capriel, and G. Binsch Tetrahedron 35 1979 2661 2668
42. W. Dmowski J. Fluorine Chem. 18 1981 25 30
43. H.J. Frohn, and V.V. Bardin Z. Anorg. Allg. Chem. 630 2004 1022 1024
44. J.J. Drysdale, and W.D. Phillips J. Am. Chem. Soc. 79 1957 319 322