Application of trimethylvinylsilane as a convenient synthetic precursor of (perfluoroalkyl)ethenes: An unusual fluoride-induced elimination-desilylation coupled reaction

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2347-2349

  Szlávik, Zoltán ^a   Tárkányi, Gábor ^a,b   Gömöry, Ágnes ^a,c   Rábai, József ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b GEDEON RICHTER LTD   (Hungary)

^c CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0043027938     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006105o     Document Type: Article

References (25)

1. (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
2. (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
3. Curran, D. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1175.
4. (a) Alvey, L. J.; Rutherford, D.; Juliette, J. J. J.; Gladysz, J. A. J. Org. Chem. 1998, 63, 6302.
5. (b) Brown, H. C.; Chen, G.; Jennings, M. P.; Ramachandran, P. V. Angew. Chem., Int. Ed. 1999, 38, 2052.
6. (c) Richter, B.; de Wolf, E.; van Koten, G.; Deelman, B.-J. J. Org. Chem. 2000, 65, 3885.
7. (a) Brace, N. O.; Marshall, L. W.; Pinson, C. J.; Wingerden, G. J. Org. Chem. 1984, 49, 2361.
8. (b) Améduri, B.; Boutevin, B.; Nouiri, M.; Talbi, M. J. Fluorine Chem. 1995, 74, 191.
9. (a) Brace, N. O. U.S. Patent 3016406, 1962; Chem. Abstr. 1962, 57, 2078a.
10. (b) Brace, N. O. U.S. Patent 3145222, 1964; Chem. Abstr. 1964, 61, 10589.
11. 3 (n = 6, 8): (a) Chen, Q. Y.; Yang, Z. Y.; Zhao, C. X.; Qiu, Z. M. J. Chem. Soc., Perkin Trans. 1 1988, 563.
12. (b) Fuchikami. T.; Ojima. I. Tetrahedron Lett. 1984, 25, 303.
13. (c) Beyou, E.; Babin, P.: Bennetau, B.; Dunogues, J.; Teyssie, D.; Boileau, S. Tetrahedron Lett. 1995, 11, 1843.
14. s); 1240.2, 1207.2 (CF).
15. 2O; 98%, Aldrich) was used as received.
16. as); 1245.2, 1202.7 (CF).
17. (a) Clark, J. H. Chem. Rev. 1980, 80, 429.
18. (b) Cunico, R. F.; Dexheimer, E. M. J. Am. Chem. Soc. 1972, 94, 2868.
19. 2I; 19.29 min, 38.5%, 3.
20. 3 was identified through preparation from the reaction of 3 with KOH: Chen, Q. Y.; Yang, Z. Y.; Rong, D. Q. J. Fluorine Chem. 1985, 29, 147.
21. Szlávik, Z.; Csámpai, A.; Krafft, M. P.; Riess, J. G.: Rábai, J. Tetrahedron Lett. 1997, 38, 8757.
22. Takahashi, M.; Nagasaki, Y.; Fujii, S. Jpn. Patent 02169528, 1990; Chem. Abstr. 1993, 113, 190741q.
23. s): 1209.9, 1149.9 (CF).
24. Puy, M.; Poss, A. J.; Persichini, P. J.; Ellis, L. A. S. J. Fluorine Chem. 1994, 67, 215.
25. Kupče, E.; Freeman, R. J. Magn. Reson. A 1995, 115, 273.