A new route to 1,1-difluoroolefins

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 5989-5992

  Tellier, Frédérique ^a   Baudry, Monique ^b   Sauvêtre, Raymond ^b  

^a CEMAGREF   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; FLUORINATION; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030788729     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01363-4     Document Type: Article

References (42)

1. Prestwich, G.D. Pestic. Sci. 1986, 37, 430-440.
2. i) Prestwich, G.D.; Sun, W.C.; Mayer, M.S.; Dickens, J.C. J. Chem. Ecol. 1990, 16, 1761-1789;
3. Filler, R.; Kobayashi, Y. Biomedical Aspects of Fluorine Chemistry; Kodansha & Elsevier Biomedical: Tokyo, 1982.
4. Moore, W.R.; Schatzman, G.L.; Jarvi, E.T.; Gross, R.S.; McCarthy, J.R. J. Am. Chem. Soc. 1992, 114, 360-361.
5. i) Bey, P.; McCarthy, J.R.; McDonald, I.A. Effects of Selective Fluorination on Reactivity, ACS Symposium Series 456, American Chemical Society: Washington, D.C., 1991, pp 105-133;
6. McCarthy, J. R.; Matthews, D.P.; Stemerick, D.M.; Huber, E.W.; Bey, P.; Lippert, B.J.; Snyder, R.D.; Sunkara, P.S. J. Am. Chem. Soc. 1991, 113, 7439-7440 and references cited therein.
7. Welch, J.T. Tetrahedron 1987, 43, 3123-3197.
8. Motherwell, W.B.; Tozer, M.J.; Ross, B.C. J. Chem. Soc., Chem. Commun. 1989, 1437-1439.
9. i) Fuqua, S.A.; Duncan, W.G.; Silverstein, R.M. Tetrahedron Lett. 1964, 1461-1463;
10. Fuqua, S.A.; Duncan, W.G.; Silverstein, R.M. J. Org. Chem 1965, 30, 1027-1029;
11. Burton, D.J.; Herkes, F.E. Tetrahedron Lett. 1965, 4509-4514;
12. Burton, D.J.; Herkes, F.E. Tetrahedron Lett. 1965, 1883-1887;
13. Fuqua, S.A.; Duncan, W.G.; Silverstein, R.M. J. Org. Chem 1965, 30, 2543-2545;
14. Hayashi, S.; Nakai, T.; Ishikawa, N.; Burton, D.J.; Naae, D.G.; Kesling, H.S. Chem Lett. 1979, 983-986;
15. Wheaton, G.A.; Burton, D.J. J. Org. Chem. 1983, 48, 917-927;
16. Edwards, M.L.; Stemerick, D.M.; Jarvi, E.T.; Matthews, D.P.; McCarthy, J.R. Tetrahedron Lett. 1990, 31, 5571-5574.
17. i) Matthews, D.P.; Miller, S.C.; Jarvi, E.T.; Sabol, J.S.; McCarthy, J.R. Tetrahedron Lett. 1996, 34, 3057-3060;
18. Kim, K.-I.; McCarthy, J.R. Tetrahedron Lett. 1996, 37, 3223-3226.
19. i) Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644;
20. Percy, J.M. Tetrahedron Lett. 1990, 31, 3931-3932;
21. Patel, S.T.; Percy, J.M. J. Chem. Soc., Chem. Commun. 1992, 1477-1478;
22. Bennett, A.J.; Percy, J.M.; Rock, M.H. Synlett. 1992, 483-484;
23. Lee, J.; Tsukasaki, M.; Snieckus, V. Tetrahedron Lett. 1993, 34, 415-418;
24. Sauvêtre, R.; Normant, J.F. Tetrahedron Lett. 1981, 22, 957-958;
25. Kirihara, M.; Takuwa, T.; Takizawa, S.; Momose, T. Tetrahedron Lett. 1997, 38, 2853-2854.
26. i) Tellier, F.; Sauvêtre, R.; Normant, J.F. J. Organomet. Chem. 1986, 303, 309-315;
27. Gillet, J.P.; Sauvêtre, R.; Normant, J.F. Synthesis 1986, 538-543;
28. Tellier, F.; Sauvêtre, R.; Normant, J.F. Tetrahedron Lett. 1986, 27, 3147-3148;
29. Tellier, F.; Sauvêtre, R.; Normant, J.F. J. Organomet. Chem. 1987, 328, 1-13;
30. Tellier, F.; Sauvêtre, R.; Normant, J.F. J. Organomet. Chem. 1987, 331, 281-298;
31. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779-3782;
32. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett. 1992, 739-740.
33. Tsukamoto, T.; Kitazume, T. Synlett. 1992, 977-979.
34. i) Tellier, F.; Sauvêtre, R. Tetrahedron Lett. 1995, 36, 4221-4222;
35. Tellier, F.; Sauvêtre, R. J. of Fluorine Chem. 1996, 76, 79-82.
36. 4OH solution. The vinylic difluorinated products obtained are then purified by flash silica-gel chromatography (cyclohexane).
37. 2, J = 55 and 27 Hz) ppm.
38. 2, J = 52 and 24 Hz) ppm.
39. Hiyama, T.; Obayashi, M.; Sawabata, M. Tetrahedron Lett. 1983, 24, 4113-4116.
40. 19F NMR δ: Z-isomer: -101.6 (ddd, 1F, J = 250, 13 and 11 Hz); -102.3 (ddd, 1F, J = 250, 13 and 11 Hz) ppm; E-isomer: -105.8 (dt, 1F, J = 246 and 10 Hz); -106.9 (dt, 1F, J = 246 and 10 Hz) ppm.
41. 19F NMR δ: E-isomer: -118.6 (dq, J = 18 and 5 Hz) ppm; Z-isomer: -124.6 (dq, J = 31 and 3 Hz) ppm.
42. Still, W.C. J. Org. Chem. 1976, 41, 3063-3064.