Advertisement

Directionality in Formation of Small Rings by Intramolecular Nucleophilic Substitution

  • C. J. M. Stirling
Part of the NATO ASI Series book series (ASIC, volume 273)

Abstract

The formation of small rings by intramolecular nucleophilic substitution is examined with respect to the activation parameters for such processes set beside calculations of the transition structure dimension and the problem of alignment of nucleophile, electrophile and leaving group. The consequences of restraint on the leaving group trajectory are considered in the light of synthetically useful procedures involving intramolecular attack on strained rings and the often inefficient harnessing of strain in the acceleration of elimination reactions.

Keywords

Transition Structure Ring Closure Ring Size Small Ring Epoxy Carbon 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References and Footnotes

  1. 1.
    A.C. Knipe and C.J.M. Stirling, J. Chem. Soc. (B), 1967, 808.Google Scholar
  2. 2.
    C.H.M. Stirling, J. Chem. Ed., 1973, 50, 84.CrossRefGoogle Scholar
  3. 3.
    A.C. Knipe and C.J.M. Stirling, J. Chem. Soc. (B), 1968, 67.Google Scholar
  4. 4.
    R. Bird, A.C. Knipe and C.J.M. Stirling, J. Chem. Soc., Perkin II, 1973, 1215.Google Scholar
  5. 5.
    B. Issari and C.J.M. Stirling, J. Chem. Soc. Perkin Trans. II, 1984, 1043.Google Scholar
  6. 6.
    R. Bird, G. Griffiths, G.F. Griffiths and C.J.M. Stirling, J. Chem. Soc. Perkin Trans. II, 1982, 579.Google Scholar
  7. 7.
    F. Benedetti and C.J.M. Stirling, Chem. Soc. Perkin Trans. II, 1986. 605.CrossRefGoogle Scholar
  8. 8.
    F. Benedetti, S. Fabrissin, A. Rusconi and C.J.M. Stirling, Gazz. Chim. Ital., 1988, 118, 233.Google Scholar
  9. 9.
    S.M. van der Kerk, J.W. Verhoeven and C.J.M. Stirling, J. Chem. Soc. Perkin Trans. II, 1985, 1355.Google Scholar
  10. 10.
    N. Isaacs, ‘Physical Organic Chemistry’, Longmans, London, 1987, p. 381.Google Scholar
  11. 11.
    L. Tenud, S. Farooq, J. Seibl and A. Eschenmoser, Helv. chim. Acta, 1970, 53, 2059.CrossRefGoogle Scholar
  12. 12.
    D.H. Heathcock, T.W. von Geldern, C.B. Lebrilla and W.F. Maier, Org. Chem., 1985, 50, 968.CrossRefGoogle Scholar
  13. 13.
    L.A. Paquette, Workshop comment.Google Scholar
  14. 14a.
    G. Stork, L.D. Cama and D.R. Coulson, J. Am. Chem. Soc., 1974, 96, 5268CrossRefGoogle Scholar
  15. 14b.
    G. Stork and J.F. Cohen, J. Am. Chem. Soc., 1974, 96, 5270.CrossRefGoogle Scholar
  16. 15.
    J.Y. Lallemand and M. Onanga, Tetrahedron Lett., 1975, 585.Google Scholar
  17. 16.
    F. Benedetti, S. Fabrissin, T. Gianferrara and A. Risaliti, J. Chem. Soc. Chem. Commun., 1987, 406.Google Scholar
  18. 17a.
    J.I. Lynas-Gray and C.J.M. Stirling, unpublished work.Google Scholar
  19. 17. (b)
    S. Hughes, G. Griffiths and C.J.M. Stirling, J. Chem. Soc. Perkin Trans. II, 1987, 1253.Google Scholar
  20. 17. (c)
    D.J. Young and C.J.M. Stirling, J. Chem. Soc. Chem. Commun., 1987, 552.Google Scholar

Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • C. J. M. Stirling
    • 1
  1. 1.Department of ChemistryUniversity College of North WalesGwyneddUK

Personalised recommendations