Synthetic and mechanistic aspects of the reactions between bromodifluoromethyltriphenylphosphonium bromide and dibromofluoromethyltriphenylphosphonium bromide and trialkylphosphites

Journal of Fluorine Chemistry

Volumn 129, Issue 7, 2008, Pages 583-589

  Flynn, Richard M ^a   Burton, Donald J ^a   Wiemers, Denise M ^a  

^a University of Iowa   (United States)

Author keywords

Bromodifluoromethylphosphonates; Bromodifluoromethyltriphenylphosphonium salts; Bromofluoromethylene ylide; Bromofluoroolefins; Dibromofluoromethyltriphenylphosphonium salts; Difluorocarbene; Difluoromethylene ylide; Exchange reactions

Indexed keywords

EID: 46749088930     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.04.003     Document Type: Article

References (24)

1. Burton D.J., Yang Z.-Y., and Qiu W. Chem. Rev. 96 (1996) 1641-1715
2. Burton D.J., Naae D.G., Flynn R.M., Smart B.E., and Brittelli D.R. J. Org. Chem. 48 (1983) 3616-3618
3. D.G. Naae, Ph.D. Thesis, University of Iowa, 1972.
4. H.S. Kesling III, Ph.D. Thesis, University of Iowa, 1975.
5. Burton D.J. J. Fluorine Chem. 23 (1983) 339-357
6. Cox D.G., and Burton D.J. J. Org. Chem. 53 (1988) 366-374
7. Cox D.G., Gurusamy N., and Burton D.J. J. Am. Chem. Soc. 107 (1985) 2811-2812
8. Burton D.J., and Naae D.G. J. Am. Chem. Soc. 95 (1973) 8467-8468
9. Mark V., Dungan C.H., Crutchfield M.M., and Van Wazer J.R. Top. Phosphorus Chem. 5 (1967) 227
10. Flynn R.M., Manning R.G., Kessler R.M., Burton D.J., and Hansen S.W. J. Fluorine Chem. 18 (1981) 525-531
11. Burton D.J., and Flynn R.M. J. Fluorine Chem. 10 (1977) 329-332
12. R.M. Flynn, Ph.D. Thesis, University of Iowa, 1979, pp. 78-79.
13. 2H.
14. Similar to the reaction outlined in Eq. (6), the trialkylphosphonium salts appear to be unique in the formation of bis analogs.
15. Burton D.J., Flynn R.M., Manning R.G., and Kessler R.M. J. Fluorine Chem. 21 (1982) 371-376
16. 19F NMR analysis of the reaction mixture and the reaction was not clean. Thus, this route is not a good synthetic route to difluoromethylene alkenes.
17. Burton D.J., and Hahnfeld J.L. J. Org. Chem. 42 (1977) 828-831
18. Vander Haar R.W., Burton D.J., and Naae D.G. J. Fluorine Chem. 1 (1971/1972) 381-383
19. R.W. Vander Haar, Ph.D. Thesis, University of Iowa, 1973.
20. Birchall J.M., and Haszeldine R.N. J. Chem. Soc. 13 (1959)
21. This yield was reported as a preliminary result in Ref. [2].
22. CP = 238 Hz).
23. CP = 237 Hz).
24. HF [(E) and (Z)] to assign the configuration of fluoroolefins see, D.J. Burton, H.C. Krutzsch, J. Org. Chem. 35 (1970) 2125-2130, X. Zhang, L. Lu, D.J. Burton, Collect. Czech. Chem. Commun. 67 (2002) 1247-1261 and J.W. Emsley, L. Phillips, V. Wray, Fluorine Coupling Constants, Pergamon, NY, 1977.