Formation of 6,8-di-tert-butyl-3,4-dihydro-4,4-dimethyl-1-phosphanaphthalene by the reaction of 2,2-dibromo-1-(2,4,6-tri-tert-butylphenyl)-1-phosphaethene with butyllithium

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Shigekazu Ito, Kozo Toyota and Masaaki Yoshifuji


Abstract

Sterically crowded 1-bromo-2-(2,4,6-tri-tert-butylphenyl)- 2-phosphaethenyllithium gave 6,8-di-tert-butyl-3,4-dihydro-4,4-dimethyl-1-phosphanaphthalene by intramolecular insertion of an intermediary phosphinidene carbene species into one of the C–H bonds of the two o-tert-butyl groups.


References

  1. M. Regitz and O. J. Scherer, Multiple Bonds and Low Coordination in Phosphorus Chemistry, Georg Thieme Verlag, Stuttgart, 1990 Search PubMed.
  2. M. Yoshifuji, I. Shima, N. Inamoto, K. Hirotsu and T. Higuchi, J. Am. Chem. Soc., 1981, 103, 4587 CrossRef CAS; 1982, 104, 6167.
  3. M. Yoshifuji, K. Toyota, K. Shibayama and N. Inamoto, Tetrahedron Lett., 1984, 25, 1809 CrossRef CAS; M. Yoshifuji, K. Toyota and N. Inamoto, J. Chem. Soc., Chem. Commun., 1984, 689 RSC See also: H. H. Karsch, F. H. Köhler and H.-U. Reisacher, Tetrahedron Lett., 1984, 25, 3687 Search PubMed; R. Appel, P. Fölling, B. Josten, M. Siray, V. Winkhaus and F. Knoch, Angew. Chem., Int. Ed. Engl., 1984, 23, 619 CrossRef CAS.
  4. M. Yoshifuji, T. Niitsu and N. Inamoto, Chem. Lett., 1988, 1733 CAS; M. Yoshifuji, H. Kawanami, Y. Kawai, K. Toyota, M. Yasunami, T. Niitsu and N. Inamoto, Chem. Lett., 1992, 1053 CAS See also: R. Appel and M. Immenkeppel, Z. Anorg. Allg. Chem., 1987, 553, 7 Search PubMed.
  5. M. Yoshifuji, S. Ito, K. Toyota and M. Yasunami, Bull. Chem. Soc. Jpn., 1995, 68, 1206; S. Ito, K. Toyota and M. Yoshifuji, Chem. Lett., 1995, 747 CAS; M. van der Sluis, F. Bickelhaupt, N. Veldman, H. Kooijman, A. L. Spek, W. Eisfeld and M. Regitz, Chem. Ber., 1995, 128, 465 CAS.
  6. R. Appel, C. Casser and M. Immenkeppel, Tetrahedron Lett., 1985, 26, 3551 CrossRef CAS.
  7. M. van der Sluis, J. B. M. Wit and F. Bickelhaupt, Organometallics, 1996, 15, 174 CrossRef CAS; H. Ramdane, H. Ranaivonjatovo, J. Escudié, S. Mathieu and N. Knouzi, Organometallics, 1996, 15, 3070 CrossRef CAS.
  8. S. J. Goede and F. Bickelhaupt, Chem. Ber., 1991, 124, 2677 CAS.
  9. R. H. Fischer, M. Baumann and G. Köbrich, Tetrahedron Lett., 1974, 1207 CAS.
  10. M. T. Nguyen and T.-K. Ha, J. Mol. Struct: THEOCHEM, 1986, 139, 145 CrossRef.
  11. M. Yoshifuji, K. Toyota, N. Inamoto, K. Hirotsu and T. Higuchi, Tetrahedron Lett., 1985, 26, 6443 CrossRef CAS; M. Yoshifuji, K. Toyota, I. Matsuda, T. Niitsu, N. Inamoto, K. Hirotsu and T. Higuchi, Tetrahedron, 1988, 44, 1363 CrossRef CAS; R. Appel, J. Menzel, F. Knoch and P. Volz, Z. Anorg. Allg. Chem., 1986, 534, 100 CrossRef CAS.
  12. G. Märkl and W. Bauer, Angew. Chem., Int. Ed. Engl., 1989, 28, 1695 CrossRef.
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