View PDF Version
 
DOI: 10.1039/A707948F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 875-880

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 12.1 Extrusion of Ph3P from sulfonyl ylides and reactivity of the resulting sulfonyl carbenes

(Note: The full text of this document is currently only available in the PDF Version )

R. Alan Aitken, Martin J. Drysdale, George Ferguson and Alan J. Lough

Abstract

Twelve sulfonyl stabilised phosphorus ylides have been prepared and their behaviour upon flash vacuum pyrolysis at 600 °C has been examined. Examples with an arylsulfonyl substituent undergo loss of Ph3PO to give intractable products but those with an arylmethylsulfonyl substituent separately lose Ph3P and SO2 to give products consistent with the intermediacy of sulfonyl carbenes. X-Ray structure determinations of one ylide from each series show a more significant P–O non-bonding interaction in the first case, providing some explanation for the different thermal reactivity.

References

  1. Part 11, R. A. Aitken, I. M. Fairhurst, A. Ford, P. E. Y. Milne, D. W. Russell and M. Whittaker, J. Chem. Soc., Perkin Trans. 1, 1997, 3107 Search PubMed.
  2. H. Staudinger and E. Hauser, Helv. Chim. Acta, 1921, 4, 861 CrossRef CAS.
  3. A. M. van Leusen, B. A. Reith, A. J. W. Iedema and J. Strating, Recl. Trav. Chim. Pays-Bas, 1972, 91, 37 CAS.
  4. Preliminary communication, R. A. Aitken and M. J. Drysdale, J. Chem. Soc., Chem. Commun., 1991, 512 Search PubMed.
  5. W. Davies and J. H. Dick, J. Chem. Soc., 1931, 2104 RSC.
  6. B. A. Reith, J. Strating and A. M. van Leusen, J. Org. Chem., 1974, 39, 2728 CrossRef CAS.
  7. B. C. Smith and G. H. Smith, J. Chem. Soc., 1965, 5516 RSC; E. Fluck and H. Binder, Z. Anorg. Allg. Chem., 1967, 354, 139 CAS.
  8. R. A. Aitken, I. Gosney and J. I. G. Cadogan, Prog. Heterocycl. Chem., 1992, 4, 1 Search PubMed.
  9. Y. Ito, M. Okano and R. Oda, Tetrahedron, 1967, 23, 2137 CrossRef CAS.
  10. H. Nozaki, M. Takaku, Y. Hayashi and K. Kondo, Tetrahedron, 1968, 24, 6563 CrossRef CAS; J. Ide and Y. Yura, Tetrahedron Lett., 1968, 3491 CrossRef CAS.
  11. R. J. Mulder, A. M. van Leusen and J. Strating, Tetrahedron Lett., 1967, 3057 CrossRef.
  12. B. E. Sarver, M. Jones and A. M. van Leusen, J. Am. Chem. Soc., 1975, 97, 4771 CrossRef CAS and references therein.
  13. M. Hrytsuk, N. Etkin and T. Durst, Tetrahedron Lett., 1986, 27, 5679 CrossRef.
  14. J. I. G. Cadogan, J. B. Husband and H. McNab, J. Chem. Soc., Perkin Trans. 2, 1983, 697 RSC.
  15. G. Wittig and W. Böll, Chem. Ber., 1962, 95, 2526 CrossRef CAS.
  16. E. Anders, T. Clark and T. Gassner, Chem. Ber., 1986, 119, 1350 CrossRef CAS.
  17. A. J. Speziale and K. W. Ratts, J. Am. Chem. Soc., 1965, 87, 5603 CrossRef CAS; P. J. Wheatley, J. Chem. Soc., 1965, 5785 RSC.
  18. E. Späth, Monatsh. Chem., 1913, 34, 1965.
  19. W. Davies and J. H. Dick, J. Chem. Soc., 1932, 483 RSC.
  20. R. A. Aitken and J. I. Atherton, J. Chem. Soc., Perkin Trans. 1, 1994, 1281 RSC.
  21. E. J. Gabe, Y. Le Page, J.-P. Charland, F. L. Lee and P. S. White, J. Appl. Crystallogr., 1989, 22, 384 CrossRef.
  22. G. M. Sheldrick, SHELXS97, Program for the solution of crystal structures, 1997, University of Göttingen, Germany.
  23. G. M. Sheldrick, SHELXL97, Program for the refinement of crystal structures, 1997, University of Göttingen, Germany.
  24. C. K. Johnson, ORTEP—A Fortran Thermal Ellipsoid Plot Program, Technical Report ORNL-5138, 1976, Oak Ridge National Laboratory, USA.
  25. A. L. Spek, PLATON Molecular Geometry and Graphics Program, September 1997 version, University of Utrecht, Netherlands.
Click here to see how this site uses Cookies. View our privacy policy here.