Comparative study of the ring opening of 1-CF3-epoxy ethers mediated by Brönsted acids and hexafluoro-2-propanol

Journal of Fluorine Chemistry

Volumn 126, Issue 4, 2005, Pages 549-554

  Iskra, Jernej ^a,b   Bonnet Delpon, Danièle ^a   Bégué, Jean Pierre ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b JO EF STEFAN INSTITUTE   (Slovenia)

Author keywords

Br nsted acid; Fluorinated alcohols; Hexafluoro 2 propanol; Hydrogen bonds; Oxirane ring opening; Trifluoromethyl ketones; Trifluoromethyl epoxy ethers

Indexed keywords

EID: 23244462147     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2004.12.008     Document Type: Article

References (45)

1. J.P. Bégué, and D. Bonnet-Delpon Tetrahedron 47 1991 3207 3258
2. N.P. Peet, J.P. Burkhart, M.R. Angelastro, E.L. Giroux, S. Mehdi, P. Bey, M. Kolb, B. Neises, and D. Schirlin J. Med. Chem. 33 1990 394 407
3. M.F. Parisi, and R.H. Abeles Biochemistry 31 1992 9429 9435
4. D.V. Patel, K. Rielly-Gauvin, D.E. Ryono, C.A. Free, S.A. Smith, and E.W. Petrillo J. Med. Chem. 36 1993 2431 2447
5. P. Warner, R.C. Green, B. Gomes, and A.M. Strimper J. Med. Chem. 37 1994 3090 3099
6. D.L. Boger, H. Sato, A.E. Lerner, B.J. Austin, J.E. Patterson, M.P. Patricelli, and B.F. Cravatt Bioorg. Med. Chem. Lett. 9 1999 265 270
7. J.P. Bégué, D. Bonnet-Delpon, and H. Sdassi Tetrahedron Lett. 33 1992 1879 1882
8. A. Abouabdellah, J.P. Bégué, D. Bonnet-Delpon, A. Kornilov, I. Rodrigues, and C. Richard J. Org. Chem. 63 1998 6529 6534
9. J.P. Bégué, D. Bonnet-Delpon, A. Kornilov, and N. Fischer-Durand J. Fluorine Chem. 80 1996 13 16
10. J.P. Bégué, D. Bonnet-Delpon, and A. Kornilov Synthesis 1996 529 532
11. J.P. Bégué, F. Benayoud, and D. Bonnet-Delpon J. Org. Chem. 60 1995 5029 5036
12. L. Eberson, M.P. Hartshorn, O. Persson, and F. Radner Chem. Commun. 1996 2105 2112
13. I. Sirangelo, P. Dal Piaz, C. Malmo, M. Casillo, L. Birolo, P. Pucci, G. Marino, and G. Irace Biochemistry 42 2003 312 319
14. L.A. Munishkina, C. Phelan, V.N. Uversky, and A.L. Fink Biochemistry 42 2003 2720 2730
15. M. Fioroni, M.D. Diaz, and S. Berger J. Am. Chem. Soc. 124 2002 7737 7744 and references cited therein
16. D.N. Kevill, and M.J. D'Souza J. Phys. Org. Chem. 15 2002 881 888
17. J.P. Richard, M.M. Toteva, and T.L. Amyes Org. Lett. 3 2001 2225 2228
18. K.-T. Liu, and H.-I. Chen J. Chem. Soc., Perkin Trans. 2 2000 893 898
19. F.L. Schadt, T.V. Bentley, and P.V.R. Schleyer J. Am. Chem. Soc. 98 1976 7667 7674
20. R. Ben-Daniel, S.P. de Visser, S. Shaik, and R. Neumann J. Am. Chem. Soc. 125 2003 12116 12117
21. U. Habusha, E. Rozental, and S. Hoz J. Am. Chem. Soc. 124 2002 15006 15011
22. R. Takita, T. Ohshima, and M. Shibasaki Tetrahedron Lett. 43 2002 4661 4665
23. T.G. Levitskaia, B.A. Moyer, P.V. Bonnesen, A.P. Marchand, K. Krishnudu, Z. Chen, Z. Huang, H.G. Kruger, and A.S. McKim J. Am. Chem. Soc. 123 2001 12099 12100
24. H. Abe, H. Amii, and K. Uneyama Org. Lett. 3 2001 313 315
25. J.P. Bégué, D. Bonnet-Delpon, and B. Crousse Synlett 2004 18 29
26. J. Iskra, D. Bonnet-Delpon, and J.P. Bégué Tetrahedron Lett. 43 2002 1001 1003
27. J. Legros, B. Crousse, D. Bonnet-Delpon, and J.-P. Bégué Eur. J. Org. Chem. 2002 3290 3293
28. K.S. Ravikumar, Y.M. Zhang, J.P. Bégué, and D. Bonnet-Delpon Ew. J. Org. Chem. 1998 2937 2940
29. S. Kobayashi, H. Tanaka, H. Amii, and K. Uneyama Tetrahedron 59 2003 1547 1552
30. A. Berkessel, M.R.M. Andreae, H. Schmickler, and J. Lex Angew. Chem. Int. Ed. 41 2002 4481 4484
31. K. Neimann, and R. Neumann Org. Lett. 2 2000 2861 2863
32. G.-J. ten Brink, J.M. Vis, I.W.C.E. Arends, and R.A. Sheldon Tetrahedron 58 2002 3977 3983
33. G.-J. ten Brink, J.M. Vis, I.W.C.E. Arends, and R.A. Sheldon J. Org. Chem. 66 2001 2429
34. V. Kesavan, D. Bonnet-Delpon, and J.P. Bégué Tetrahedron Lett. 41 2000 2895 2898
35. U. Das, B. Crousse, V. Kesavan, D. Bonnet-Delpon, and J.P. Bégué J. Org. Chem. 65 2000 6749 6751
36. I. Rodrigues, D. Bonnet-Delpon, and J.P. Bégué J. Org. Chem. 66 2001 2098 2103
37. J. Iskra, D. Bonnet-Delpon, and J.P. Bégué Eur. J. Org. Chem. 2002 3402 3410
38. M.H. Abraham, P.L. Grellier, D.V. Prior, J.J. Morris, and P.J. Taylor J. Chem. Soc., Perkin Trans. 2 1990 521 529
39. C. Laurence, M. Berthelot, J.-Y. Le Questel, and M.J. El Ghomari J. Chem. Soc., Perkin Trans. 2 1995 2075 2079
40. A. Abouabdellah, J.P. Bégué, D. Bonnet-Delpon, A. Kornilov, I. Rodrigues, and C. Richard J. Org. Chem. 63 1998 6529 6534
41. D. Farcasiu, A. Ghenciu, G. Marino, and R.V. Kastrup J. Mol. Cat. A 126 1997 141 150
42. J.P. Bégué, D. Bonnet-Delpon, D. Mesureur, G. Née, and S.-W. Wu J. Org. Chem. 57 1992 3807 3814
43. J.P. Bégué, D. Bonnet-Delpon, and A. Kornilov Org. Synth. 75 1998 153 159
44. F. Benayoud, J.P. Bégué, D. Bonnet-Delpon, N. Fischer-Durand, and H. Sdassi Synthesis 1993 1083 1085
45. V.S. Karavan, V.G. Tribulovich, and V.A. Nikiforov Zh. Org. Khim. 28 1992 1455 1459