Alkylation and decarboxylation of ethyl 2-fluoro-3-oxobutanoate as a route to functionalised α-fluoro-ketones

Tetrahedron

Volumn 54, Issue 12, 1998, Pages 2867-2876

  Hutchinson, J ^a,b   Sandford, Graham ^a   Vaughan, Julian F S ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b F2 Chemicals Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROCARBON; KETONE DERIVATIVE;

ALKYLATION; ARTICLE; DECARBOXYLATION; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0032546242     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83023-8     Document Type: Article

References (25)

1. Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry, Principles and Commercial Applications; Plenum: New York, 1994.
2. Wilkinson, J. A. Chem. Rev. 1992, 92, 505.
3. Resnati, G. Tetrahedron 1993,49, 9385.
4. Takeuchi, Y. J. Synth. Org. Chem. Jpn. 1988,46, 145.
5. Iseki. K.; Kobayashi, Y. Rev. Heteroatom. Chem. 1995, 12, 211,
6. Percy, J. M. Contemporary Org. Synth. 1995, 251.
7. Percy, J. M. Top. Curr. Chem, 1997,193, 131.
8. March, J. Advanced Organic Chemistry, 3rd ed.; John Wiley and Sons: New York, 1985.
9. Rozen, S.; Filler, R. Tetrahedron 1985, 41, 1111.
10. Chambers, R, D.; Greenhall, M. P.; Hutchinson, J. Tetrahedron 1996,52, 1.
11. Chambers, R. D.; Hutchinson, J.; Thomson, J. J. Fluorine Chem. 1996, 78, 165.
12. Chambers, R. D.; Hutchinson, J.; Batsanov, A. S.; Lehmann, C. W.; Naumov, D. Y. J. Chem. Soc., Perkin Trans. I 1996,2271.
13. F2 Chemicals Ltd, now manufacture α-fluoro-β-ketoesters on a large scale (>500kg) by direct fluorination methodology .
14. deMontellano, P. R. O.; Vinson, W, A. J. Org. Chem. 1977,42, 2013.
15. Kitazume, T.; Nakayama, Y. J. Org. Chem. 1986, 51, 2795.
16. Bergman, E. D.; Cohen, S.; Shahak, I. J. Chem. Soc. 1959, 3278.
17. Bumgardner, C. L.; Sloop, J, C, J. Fluorine Chem. 1992,56, 141.
18. Machleidt, H.; Hartmann, V. Liebigs Ann. Chem. 1964, 679, 9.
19. Everett, T. S. In Chemistry of Organic Fluorine Compounds II; Hudlicky, M.; Pavlath, A. E. Eds.; American Chemical Society: Washington D.C., 1995,
20. Chambers, R. D. Fluorine in Organic Chemistry; John Wiley and Sons: New York, 1973.
21. Huckin, S. N,; Weiler, L. J. Am. Chem. Soc. 1974,96, 1082.
22. Banthorpe, D. V.; Ireland, M. J. J. Prakt. Chem. 1996, 338, 279.
23. Middleton, W. J.; Bingham, E. M. J. Am. Chem. Soc. 1980,102, 4845.
24. Allinger, N. L.; Blatter, H. M. J. Org. Chem. 1962, 27, 1523.
25. Welch, J. T.; Seper, K. W. J. Org. Chem. 1988, 53, 2991.