Generation of acetylides by treatment of fluoroethylenes with LDA: Preparation of propargyl alcohols

Synthesis

Volumn , Issue 3, 2000, Pages 452-456

  Kataoka, Kentaro ^a   Tsuboi, Sadao ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Acetylides; Dehydrofluorination; Eliminations; Fluorine; Fluoroethylenes; Propargyl alcohols; Wittig reaction

Indexed keywords

ALCOHOL DERIVATIVE; ETHYLENE DERIVATIVE; FLUORINE DERIVATIVE;

ARTICLE; FLUORINATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS;

EID: 0034052964     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6336     Document Type: Article

References (23)

1. Mizuno, K.; Wakabayashi, T.; Koinuma, Y.; Aizawa, R.; Kushiyama, S.; Kobayashi, S.; Ohuchi, H.; Yoshida, T.; Kubota, Y.; et al. German Patent 3 936 516 (1990); Chem. Abstr. 1990, 113, 158126.
2. Burton, D. J.; Cox, D. G. J. Am. Chem. Soc. 1983, 105, 650.
3. Cox, D. G.; Gurusamy, N.; Burton, D. J. J. Am. Chem. Soc. 1985, 107, 2811.
4. (a) Jeong, I. H.; Burton, D. J.; Cox, D. G. Tetrahedron Lett. 1986, 27, 3709.
5. (b) Burton, D. J.; Jeong, I. H. J. Fluorine Chem. 1993, 62, 259.
6. Cox, D. G.; Burton, D. J. J. Org. Chem. 1988, 53, 366.
7. (a) Vedejs, E.; Snoble K. A. J. J. Am. Chem. Soc. 1973, 95, 5778.
8. (b) Vedejs, E.; Meier, G. P.; Snoble K. A. J. J. Am. Chem. Soc. 1981, 103, 2823.
9. Giese, B.; Schoch, J.; Ruchardt, C. Chem. Ber. 1978, 111, 1395.
10. Bestmann, H. J.; Roth, K.; Wilhelm, E.; Bohme, R.; Burzlaff, H. Angew. Chem. Int. Ed. Engl. 1979, 18, 876.
11. Schlosser, M.; Schaub, B. J. Am. Chem. Soc. 1982, 104, 5821.
12. (a) Maffeo, C. V.; Marchese, G.; Naso, F.; Ronzini, L. J. Chem. Soc., Perkin Trans. 1 1979, 92.
13. (b) Kauffmann, T.; Saelker, R.; Voss, K. U. Chem. Ber. 1993, 126, 1447.
14. Hayashi, S.; Nakai, T.; Ishikawa, N. Chem. Lett. 1980, 651.
15. Schlosser, M.; Zimmermann, M. Synthesis 1969, 75.
16. Burton, D. J.; Greenlimb, P. E. J. Org. Chem. 1975, 40, 2796.
17. Burton, D. J.; Greenlimb, P. E. J. Fluorine Chem. 1973-74, 3, 447.
18. Fuqua, S. A.; Duncan, W. G.; Silverstein.R. M. J. Org. Chem. 1965, 30, 1027.
19. (a) Collier, W. L.; Macomber, R. S. J. Org. Chem. 1973, 38, 1367.
20. (b) Dehmlow, E. V.; Lissel, M. Liebigs Ann. Chem. 1980, 1.
21. Dakka, J.; Sasson, Y. J. Org. Chem. 1989, 54, 3224.
22. Muzart, J.; Piva, O. Tetrahedron Lett. 1988, 29, 2321.
23. Larson, D. P.; Heathcock, C. H. J. Org. Chem. 1996, 61, 5208.