A convenient one-pot synthesis of α-fluoro-α,β-unsaturated nitriles from diethyl cyanofluoromethanephosphonate

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 3, 1992, Pages 313-315

  Xu, Ze Qi ^a   DesMarteau, Darryl D ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049076821     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19920000313     Document Type: Article

References (23)

1. J. T. Welch and R. W. Herbert, J. Org. Chem., 1990, 55, 4782
2. J. T. Welch, Tetrahedron, 1987,43,3123
3. S. H. Lee and J. Schwartz, J. Am. Chem. Soc., 1986,108, 2445
4. P. Bey, J. R. McCarthy and I. A. McDonald, in Selective Fluorination in Organic and Bioorganic Chemistry, ed. J. T. Welch, ACS, Washington, DC, 1991, ch. 8, p. 105 and refs, cited therein
5. G. D. Prestwich, W. C. Sun and J. C. Dickens, J. Chem. Enol., 1988, 14, 1427
6. P. W. Collins, S. W. Kramer and G. W. Gulickson, J. Med. Chem., 1987, 30, 1952.
7. J. R. McCarthy, E. T. Jarvi, D. P. Matthews, M. L. Edwards, N. J. Prakash, T. L. Bowlin, S. Mehdi, P. S. Sunkara and P. Bey, J. Am. Chem. Soc., 1989, 111, 1127
8. E. Baader, W. Bartmann, G. Beck, P. Below, A. Bergmann, H. Jendralla, K. Kesseller and G. Wess, Tetrahedron Lett., 1989, 30, 5115
9. I. A. McDonald, J. M. Lacoste, P. Bey, M. G. Palfreyman and M. Zreik, J. Med. Chem., 1985, 28, 186.
10. Y. Allmendinger, E. Felder and E. Hungerbuehler, in Selective Fluorination in Organic and Bioorganic Chemistry, ed. J. T. Welch, ACS, Washington, DC, 1991, ch. 13, p. 186 and refs, cited therein
11. T. Allmendinger, P. Furet and E. Hungerbuehler, Tetrahedron Lett., 1990, 31, 7279
12. Y.-K. Shue, D. D. Tufano and A. M. Nadazan, Tetrahedron Lett., 1988, 29,4041.
13. H. Machleidt and R. Wessendorf, Annalen, 1964,674, 1.
14. G. Etemad-Moghadam and J. Seyden-Penne, Bull. Soc. Chim. Fr., 1985, 448
15. A. Thenappan and D. J. Burton, Tetrahedron Lett., 1989,30, 5571; J. Org. Chem., 1990,55,4369; J. Fluorine Chem., 1990, 48, 153.
16. J. R. McCarthy, D. P. Matthews, M. L. Edwards, D. M. Stemerick and E. T. Jarvi, Tetrahedron Lett., 1990, 31, 5449.
17. T. B. Patrick and S. Nadji, J. Fluorine Chem., 1990, 49, 147.
18. S. Singh, D. D. DesMarteau, S. S. Zuberi, M. Witz and H. N. Huang, J. Am. Chem. Soc., 1987, 109, 7194
19. D. D. DesMarteau and M. Witz, J. Fluorine Chem., 1991, 52, 7.
20. D. D. DesMarteau, Z.-Q. Xu and M. Wiltz, J. Org. Chem., in the press.
21. Z.-Q. Xu, D. D. DesMarteau and Y. Gotoh, J. Chem. Soc., Chem. Commun., 1991, 179
22. G. Resnati and D. D. DesMarteau, J. Org. Chem., 1991, 56, 4925.
23. Eur. Pat. Appl. EP 224,417; Chem. Abstr., 1987, 107, 96889y.