A new route to α-fluoroalkylphosphonates

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Rachel Waschbüsch, John Carran and Philippe Savignac


Abstract

Several alkylated α-fluorophosphonates have been synthesized by the reaction of an alkyl iodide, bromide (or activated chloride) with a monofluorosilyllithium phosphonate species produced either from the reaction of butyllithium, phenyllithium or other alkyllithium reagent as base and trimethylsilyl chloride with a diethyl monofluoromethylphosphonate. A study of the reaction conditions with respect to the metallating agent, silylating agent and starting monofluorophosphonate has also been undertaken.


References

  1. R. Engel, Chem. Rev., 1977, 77, 349 CrossRef CAS.
  2. P. R. Adams and R. Harrison, Biochem. J., 1974, 141, 729 CAS.
  3. G. M. Blackburn and D. E. Kent, J. Chem. Soc., Perkin Trans. 1, 1986, 913 RSC.
  4. G. R. J. Thatcher and A. S. Campbell, J. Org. Chem., 1993, 58, 2272 CrossRef CAS.
  5. D. J. Burton, Z.-Y. Yang and W. Qiu, Chem. Rev., 1996, 96, 1641 CrossRef CAS.
  6. R. D. Chambers, R. Jaouhari and D. O'Hagan, J. Chem. Soc., Chem. Commun., 1988, 1169 RSC; R. D. Chambers, R. Jaouhari and D. O'Hagan, Tetrahedron, 1989, 45, 5101 CrossRef CAS.
  7. C. Patois and P. Savignac, J. Chem. Soc., Chem. Commun., 1993, 22, 1711 RSC.
  8. D. J. Burton and R. M. Flynn, J. Fluorine Chem., 1977, 10, 329 CrossRef CAS; D. Su, W. Cen, R. L. Kirchmeier and J. M. L. Shreeve, Can. J. Chem., 1989, 67, 1795 CAS.
  9. P. Savignac, M.-P. Teulade and N. Collignon, J. Organomet. Chem., 1987, 323, 135 CrossRef CAS.
  10. M.-P. Teulade and P. Savignac, J. Organomet. Chem., 1988, 338, 295 CrossRef CAS.
  11. J. Nieschalk, A. S. Batsanov, D. O'Hagan and J. A. K. Howard, Tetrahedron, 1996, 52, 165 CrossRef CAS.
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