Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Direct Observation of an Antihomoaromatic Bicyclooctadienyl Cation

  • Shin Jung-Hyu (Department of Chemistry, Seoul National University) ;
  • Published : 1982.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

The question of the bicyclohomoaromatic stabilization and destabilization is examined. The chemistry of bicyclo(3.2.1)octa-3,6-dienide anion has been studied on order to test these concepts. The bicyclooctadienide anion is shown to be stable delocalized ion which undergoes a facile proton-deuterium exchange reaction. The solvolysis of bicyclo(3.2.1)octa-3,6-dienyl p-nitrobenzoate is much slower than the monoene analog. We have made direct observation of the bicyclooctadienyl and octenyl cations by $^{19}F$-nmr spectroscopy, and were able to demonstrate that the bicyclooctadienyl cation was bishomoantiaromatic.

Keywords

References

  1. J. Amer. Chem. Soc. v.89 R. Breslow;J. T. Groves
  2. Can. J. Chem. v.41 T. Schaefer;W. G. Schneider
  3. J. Amer. Chem. Soc. v.81 S. Winstein
  4. J. Amer Che. Soc. v.70 S. Winstein;R. Adams
  5. Chem. Soc., Spec. Publ. no.21 S. Winstein
  6. J. Amer. Chem. Soc. v.89 M. J. Goldstein
  7. Chem. Commun. J. M. Brown;J. L. Occolowitz
  8. J. Amer. Chem. Soc. v.89 S. Winstein;M. Sakai
  9. J. Amer. Chem. Soc. v.92 A. F. Diaz;M. M. Sakai
  10. J. Amer. Chem. Soc. v.89 D. G. Garnum
  11. J. Amer. Chem. Soc. v.88 S. Winstein;C. G. Kreiter
  12. J. Amer. Chem. Soc. v.85 J. Meinwald
  13. J. Amer. Chem. Soc. v.76 W. C. Wildman;D. R. Saunders