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The 2-Norbornyl Cation

  • Herbert C. Brown
Chapter

Abstract

At the time we undertook our examination of the validity of the proposals that σ-bridging represents a major factor in the rates of solvolysis, there was general acceptance for the position that cyclopropylcarbinyl (Chapter 5) and 2-norbornyl1–4 provided the most favorable examples for this phenomenon.

Keywords

Transition State Classical Structure Steric Strain Hydride Shift Endo Isomer 
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.

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References

  1. 1.
    S. Winstein and D. Trifan, J. Amer. Chem. Soc., 74, 1147, 1154 (1952).CrossRefGoogle Scholar
  2. 2.
    P. D. Bartlett, Nonclassical Ions, Benjamin, New York, 1965.Google Scholar
  3. 3.
    J. A. Berson, Molecular Rearrangements, Vol. 1, P. de Mayo, Ed., Interscience, New York, 1963, Chapter 3.Google Scholar
  4. 4.
    G. D. Sargent, Carbonium Ions, Vol. III, G. A. Olah and P. v. R. Schleyer, Eds., WileyInterscience, New York, 1972, Chapter 24.Google Scholar
  5. 5.
    H. G. Richey, Jr., Carbonium Ions, Vol. III, G. A. Olah and P. v. R. Schleyer, Eds., Wiley-Interscience, New York, 1972, Chapter 25.Google Scholar
  6. 6.
    K.B. Wiberg, B. A. Hess, and A. J. Ashe III, Carbonium Ions, Vol. III, G. A. Olah and P. v. R. Schleyer, Eds., Wiley-Interscience, New York, 1972, Chapter 26.Google Scholar
  7. 7.
    J. D. Roberts, C. C. Lee, and W. H. Saunders, Jr., J. Amer. Chem. Soc., 76, 4501 (1954).CrossRefGoogle Scholar
  8. 8.
    G. A. Olah and A. M. White, J. Amer. Chem. Soc., 91, 5801 (1969).CrossRefGoogle Scholar
  9. 9.
    G. A. Olah and A. M. White, J. Amer. Chem. Soc., 94, 808 (1972).CrossRefGoogle Scholar
  10. 10.
    M. J. S. Dewar and A. P. Marchand, Ann. Rev. Phys. Chem., 16, 321 (1965).CrossRefGoogle Scholar
  11. 11.
    F. R. Jensen and B. E. Smart, J. Amer. Chem. Soc., 91, 5686, 5688 (1969).CrossRefGoogle Scholar
  12. 12.
    T. G. Traylor, W. Hanstein, H. J. Berwin, N. A. Clinton, and R. S. Brown, J. Amer. Chem. Soc., 93, 5715 (1971).CrossRefGoogle Scholar
  13. 13.
    F. Brown, E. D. Hughes, C. K. Ingold, and J. F. Smith, Nature, 168, 65 (1951).CrossRefGoogle Scholar
  14. 14.
    H. C. Brown and F. J. Chloupek, J. Amer. Chem. Soc., 85, 2322 (1963).CrossRefGoogle Scholar
  15. 15.
    S. Winstein, E. Clippinger, R. Howe, and E. Vogelfanger, J. Amer. Chem. Soc., 87, 376 (1965).CrossRefGoogle Scholar
  16. 16.
    A. Colter, E. C. Friedrich, N. J. Holness, and S. Winstein, J. A mer. Chem. Soc., 87,378 (1965).CrossRefGoogle Scholar
  17. 17.
    G. Wagner and W. Buckner, Ber., 32, 2302 (1899).Google Scholar
  18. 18.
    H. Meerwein and K. Van Ernster, Ber., 55, 2500 (1922).Google Scholar
  19. 19.
    C. Brown, K. J. Morgan, and F. J. Chloupek, J. Amer. Chem. Soc., 87, 2137 (1965).CrossRefGoogle Scholar
  20. 20.
    H. C. Brown and C. J. Kim, J. Amer. Chem. Soc., 90, 2082 (1968).CrossRefGoogle Scholar
  21. 21.
    p. v. R. Schleyer, D. C. Kleinfelter, and H. G. Richey, Jr., J. A mer. Chem. Soc., 85, 479 (1963).CrossRefGoogle Scholar
  22. 22.
    H. Goering and K. Humski, J. Amer. Chem. Soc., 90, 6213 (1968).CrossRefGoogle Scholar
  23. 23.
    S. Winstein, J. Amer. Chem. Soc., 87, 381 (1965).CrossRefGoogle Scholar
  24. 24.
    M. Saunders, P. v. R. Schleyer, and G. A. Olah, J. Amer. Chem. Soc., 86, 5680 (1964).CrossRefGoogle Scholar
  25. 25.
    P. K. Pong, J. Amer. Chem. Soc., 96, 7638 (1974).CrossRefGoogle Scholar
  26. 26.
    G. A. Olah, A. M. White, J. R. De Member, A. Commeyras, and C. Y. Lui, J. Arner.Chem. Soc., 92, 4627 (1970).CrossRefGoogle Scholar
  27. 27.
    R. A. Sneen, Accounts Chem. Res., 6, 46 (1973).CrossRefGoogle Scholar
  28. 28.
    H. C. Brown, F. J. Chloupek, and M.-H. Rei, J. Amer. Chem. Soc., 86, 1246, 1247, 1248 (1964)CrossRefGoogle Scholar
  29. 29.
    H. L. Goering and C. B. Schewene, J. Amer. Chem. Soc., 87, 3516 (1965).CrossRefGoogle Scholar
  30. 30.
    P. v. R. Schleyer, J. Amer. Chem. Soc., 86, 1854, 1856 (1964).CrossRefGoogle Scholar
  31. 31.
    P. v. R. Schleyer, J. Amer. Chem. Soc., 89, 699 (1967).CrossRefGoogle Scholar
  32. 32.
    G. S. Hammond, J. Amer. Chem. Soc., 77, 334 (1955).CrossRefGoogle Scholar
  33. 33.
    R. Hoffman, J. Chem. Phys., 39, 1397 (1963); ibid., 40, 2480 (1964).CrossRefGoogle Scholar
  34. 34.
    W. S. Trahanovsky, J. Org. Chem., 30, 1666 (1965).CrossRefGoogle Scholar
  35. 35.
    G. Klopman, J. Amer. Chem. Soc., 91, 89 (1969).CrossRefGoogle Scholar
  36. 36.
    D. W. Goetz and L. C. Allen, XXIII International Congress of Pure and Applied Chemistry, Vol. 1, Butterworth, London, 1971, p. 51.Google Scholar
  37. 38.
    M.J. S. Dewar, R. C. Haddon, A. Komornicki, and H. Rzepa, J. Amer. Chem. Soc., 99, 377 (1977).CrossRefGoogle Scholar
  38. 39.
    W. L. Jorgensen and L. Salem, The Organic Chemist’s Book of Orbitals, Academic Press, New York, 1973.Google Scholar
  39. 40.
    H. C. Brown, I. Rothberg, P. v. R. Schleyer, M. M. Donaldson, and J. J. Harper, Proc. Nat.Acad. Sci., 56, 1653 (1966).CrossRefGoogle Scholar
  40. 41.
    R. C. Bingham, M. J. S. Dewar, and D. H. Lo, J. Amer. Chem. Soc., 97, 1294 (1975).CrossRefGoogle Scholar
  41. 42.
    L. Radom, J. A. Pople, V. Buss, and P. v. R. Schleyer, J. Amer. Chem. Soc., 94,311 (1972).CrossRefGoogle Scholar
  42. 44.
    W.L. Jorgensen, J. Amer. Chem. Soc., 99, 280 (1977).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1977

Authors and Affiliations

  • Herbert C. Brown
    • 1
  1. 1.Purdue UniversityWest LafayatteUSA

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