Generation and inter- and intra-molecular trapping of isoindenones (inden-2-ones)

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

David W. Jones and Tracie C. L. M. Ryder


Abstract

Inden-2-one and some simple derivatives are smoothly generated by reaction of caesium fluoride with 1-bromo-2-tert-butyldimethylsilyloxyindenes and they can be efficiently trapped in both intra- and inter-molecular additions; the intramolecular additions proceed with exo-addition of the tether, in contrast to the intermolecular additions and intramolecular additions to 2-benzopyran-3-ones.


References

  1. C. W. G. Fishwick and D. W. Jones, ortho-Quinonoid Compounds, in The Chemistry of Quinonoid Compounds, ed. S. Patai and Z. Rappoport, 1988, Wiley, vol. II, pp. 403–453 Search PubMed.
  2. J. M. Holland and D. W. Jones, J. Chem. Soc., Chem. Commun., 1969, 587 RSC.
  3. D. W. Jones and R. L. Wife, J. Chem. Soc., Perkin Trans. 1, 1976, 1654 RSC.
  4. J. M. Holland, PhD Thesis, University of Leeds, 1969.
  5. D. W. Jones and F. M. Nongrum, J. Chem. Soc., Perkin Trans. 1, 1995, 705 RSC.
  6. Using CHEM 3D Pro, ver. 3.5, Cambridge Soft Corporation, Cambridge, Mass.
  7. P. G. Gassman and F. V. Zalar, Tetrahedron Lett., 1964, 3031 CrossRef CAS.
  8. G. Sinha, S. K. Maji, V. R. Ghatak, M. Mukherjee, A. K. Mukerjee and A. K. Chakravarty, J. Chem. Soc., Perkin Trans. 1, 1983, 2519 RSC.
  9. M. Kamata, Y. Nishikata and M. Kato, Chem. Commun., 1996, 2407 RSC.
  10. T. Kametani, H. Kondon, M. Tsubuki and T. Honda, J. Chem. Soc., Perkin Trans. 1, 1990, 5 RSC; J. Geiwis and E. Haslinger, Helv. Chim. Acta, 1995, 78, 818 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.