Reaction of phosphaacetylenes ButC[triple bond, length as m-dash]P and 1-AdC[triple bond, length as m-dash]P with (PhSe)2–XeF2: first examples of vicinal bis-selenenylation (at P and C) to form novel phosphaalkenes

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Kenneth K. Laali, Wolfgang Fiedler and Manfred Regitz


Abstract

tert-Butyl- and 1-adamantyl-phosphaacetylenes (2 equiv.) react with (PhSe)2–XeF2 (→2 PhSeF) to give novel phosphaalkenes by vicinal bis-phenylselenenylation (at P and C), in contrast to acetylenes which undergo fluoroselenenylation.


References

  1. K. Uneyama and M. Kanai, Tetrahedron Lett., 1990, 31, 3583 CrossRef CAS.
  2. H. Poleschner, M. Heydenreich, K. Spindler and G. Haufe, Synthesis, 1994, 1043 CrossRef CAS.
  3. H. Poleschner, M. Heydenreich and U. Schilde, Leibigs. Ann., 1996, 1187 CAS.
  4. G. H. Schmid and D. G. Garrett, Tetrahedron Lett., 1975, 3991 CrossRef CAS.
  5. S. Tomoda and Y. Usuki, Chem. Lett., 1989, 1235 CAS; Y. Usuki, M. Iwaoka and S. Tomoda, Chem. Lett., 1992, 1507 CAS; Y. Usuki, M. Iwaoka and S. Tomoda, J. Chem. Soc., Chem. Commun., 1992, 1148 RSC; J. R. McCarthy, D. P. Mathews and C. L. Barney, Tetrahedron Lett., 1990, 31, 973 CrossRef CAS.
  6. K. K. Laali, B. Geissler, M. Regitz and J. J. Houser, J. Org. Chem., 1995, 60, 6362 CrossRef CAS.
  7. K. K. Laali, B. Geissler, O. Wager, J. Hoffmann, R. Armbrust, W. Eisfeld and M. Regitz, J. Am. Chem. Soc., 1994, 116, 9407 CrossRef CAS.
  8. K. K. Laali, B. Geissler, M. Regitz and J. J. Houser, J. Org. Chem., 1995, 60, 47 CrossRef CAS.
  9. K. K. Laali, M. Regitz, M. Birkel, P. J. Stang and C. M. Crittell, J. Org. Chem., 1993, 58, 4105 CrossRef CAS.
  10. K. Karaghiosoff, in Multiple Bonds and Low Coordination in Phosphorus Chemistry, ed. M. Regitz and O. J. Scherer, Thieme, Stuttgart, 1990, p. 463f Search PubMed.
  11. K. Laali, H. Y. Chen and R. J. Gerzina, J. Org. Chem., 1987, 52, 4126 CrossRef CAS.
  12. C. Saluzzo, G. Alvernhe and D. Anker, Tetrahedron Lett., 1990, 31, 2127 CrossRef CAS.
  13. T. W. Mackewitz s, PhD Dissertation, Kaiserslautern, 1996.
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