General method for the preparation of β,β-difluoroacrylates using BrF3

Journal of Organic Chemistry

Volumn 69, Issue 25, 2004, Pages 8786-8788

  Hagooly, Aviv ^a   Rozen, Shlomo ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DISULFIDE; DERIVATIVES; ESTERS; OLEFINS;

BRF3; METHYL IODIDES;

POLYACRYLATES;

ACRYLIC ACID DERIVATIVE; ALKENE; BETA,BETA DIFLUOROACRYLATE; BROMINE DERIVATIVE; BROMINE TRIFLUORIDE; BROMODIFLUOROSULFONYL DERIVATIVE; FLUORINE DERIVATIVE; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 10044278213     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0485280     Document Type: Article

References (31)

1. (a) Boguslavskaya, L. S.; Panteleeva, I. Y.; Morozova, T. V.; Kartashov, A. V.; Chuvatkin, N. N. Russ. Chem. Rev. 1990, 59, 906.
2. (b) Botteghi, C.; Paganelli, S.; Sbrogio, F.; Zarantonello, C. Tetrahedron Lett. 1999, 40, 8435.
3. (c) Castelvetro, V.; Aglietto, M.; Ciardelli, F. J. Coating Technol. 2002, 74, 57.
4. (a) McDonald, A. I.; Lacoste, M. J.; Michael, B. F.; Palfreyman, G.; Zreika, M. J. Med. Chem. 1985, 28, 186.
5. (b) Bumgardner, L. C.; Burgess, P. J.; Everett, S. T. J. Fluorine Chem. 1992, 56, 189.
6. (a) Fuchikami, T.; Shibata, Y.; Suzuki, Y. Tetrahedron Lett. 1986, 27, 3173.
7. (b) Kitazume, T.; Ohnogi, T.; Miyauchi, H.; Yamazaki, T. J. Org. Chem. 1989, 54, 5630.
8. (c) Watanabe, S.; Sugahara, K.; Fujita, T.; Sakamoto, M. J. Fluorine Chem. 1993, 62, 201.
9. (a) Kirsch, p.; Taugerbeck, A. Eur. J. Org. Chem. 2002, 3923.
10. (b) Kirsch, P.; Lenges, M.; Ruhl, A.; Sevenard, V. D.; Roschenthaler, V. G. J. Fluorine Chem. 2004, 125, 1025.
11. (c) Furuta, S.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71, 1939.
12. 3 for the preparation of modern anesthetics such as sevoflurane: (a) Rozov, L. A.; Huang, C. G.; Halpern, D. F.; Vernice, G. G.; Ramig K. Tetrahedron: Asymmetry 1997, 8, 3023.
13. (b) Halpern, D. F.; Robin, M. L. U.S. Patent 4,996,371, 1991.
14. (c) Ramig, K. Synthesis 2002, 2627.
15. (a) Rozen, S.; Mishani E.; Bar-Haim, A. J. Org. Chem. 1994, 59, 2918.
16. (b) Sasson, R.; Hagooly A.; Rozen, S. Org. Lett. 2003, 5, 769.
17. (c) Hagooly, A.; Sasson, R.; Rozen, S. J. Org. Chem. 2003, 68, 8287.
18. (d) Rozen, S.; Mishani E. Chem. Commun. 1993, 1761.
19. (a) Rozen, S.; Rechavi D.; Hagooly, A. J. Fluorine Chem. 2001, 111, 161.
20. (b) Hagooly, A.; Ben-David, I.; Rozen, S. J. Org. Chem. 2002, 67, 8430.
21. (c) Ben- David, I.; Rechavi, D.; Mishani, E.; Rozen, S. J. Fluorine Chem. 1999, 97, 75.
22. (d) Rozen, S.; Mishani E. J. Chem. Soc., Chem. Commun. 1994, 2081.
23. Rozen, S.; Lerman, O. J. Org. Chem. 1993, 58, 239.
24. (a) Rozen, S.; Ben-David, I. J. Fluorine Chem. 1996, 76, 145.
25. (b) Rozen, S.; Ben-David, I. J. Org. Chem. 2001, 66, 496.
26. Hagooly, A.; Rozen, S. Chem. Commun. 2004, 594.
27. Rozen, S.; Bareket, Y. Tetrahedron Lett. 1994, 35, 2099.
28. Boguslavskaya, L. S.; Kartashov, A. V.; Chuvatkin, N. N. Russ. J. Org. Chem. 1989, 25, 1835.
29. (a) Rozen, S.; Gal, C. J. Org. Chem. 1987, 52, 2769.
30. (b) Rozen, S.; Gal, C. J. Org. Chem. 1987, 52, 4928.
31. Bumgardner, L. C.; Burgess, P. J.; Everett, S. T.; Purrington, T. S. J. Fluorine Chem. 1992, 56, 189.