Skip to main content

Stabilized 2-Norbornyl Cations

  • Chapter
The Nonclassical Ion Problem
  • 166 Accesses

Abstract

The position that the importance of neighboring group participation should diminish as an incipient cationic center is stabilized by substitution1 appears to be generally accepted.2 Consequently, we undertook to synthesize representative 2-norbornyl systems containing a stabilizing p-anisyl group at the 2-position in order to establish its effect on the exo :endo rate and product ratios.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. S. Winstein, B. K. Morse, E. Grunwald, K. C. Schreiber, and J. Corse, J. Amer. Chem. Soc., 74, 1113 (1952).

    Article  CAS  Google Scholar 

  2. P. D. Bartlett, Nonclassical Ions, Benjamin, New York, 1965.

    Google Scholar 

  3. P. G. Gassman and A. F. Fentiman, J. Amer. Chem. Soc., 90, 2691 (1968).

    Article  Google Scholar 

  4. S. Winstein, M. Shatavsky, C. Norton, and R. B. Woodward, J. Amer. Chem. Soc., 77, 4183 (1955).

    Article  CAS  Google Scholar 

  5. H. C. Brown and K. Takeuchi, J. Amer. Chem. Soc., 88, 5336 (1966)

    Article  Google Scholar 

  6. H. C. Brown and K. Takeuchi, J. Amer. Chem. Soc., 90, 2691 (1968).

    Article  CAS  Google Scholar 

  7. S. Winstein and D. Trifan, J. Amer. Chem. Soc., 74, 1147,1154 (1952).

    Article  CAS  Google Scholar 

  8. P. v. R. Schleyer, M. M. Donaldson, and W. E. Watts, J. Amer. Chem. Soc., 87, 375 (1965).

    Article  CAS  Google Scholar 

  9. D. G. Farnum and G. Mehta, J. Amer. Chem. Soc., 91, 3256 (1969).

    Article  CAS  Google Scholar 

  10. D. G. Farnum and A. D. Wolf, J. Amer. Chem. Soc., 96, 5166 (1974).

    Article  CAS  Google Scholar 

  11. S. Winstein, J. Amer. Chem. Soc., 87, 381 (1965).

    Article  CAS  Google Scholar 

  12. P. D. Bartlett, E. R. Webster, C. E. Dills, and H. G. Richey, Ann., 623, 217 (1959).

    CAS  Google Scholar 

  13. H. C. Brown and K. Takeuchi, J. Amer. Chem.Soc., 90, 5268 (1968).

    Article  CAS  Google Scholar 

  14. A. Colter, E. C. Friedrich, N. J. Holness, and S. Winstein, J. Amer. Chem. Soc., 87, 378 (1965).

    Article  CAS  Google Scholar 

  15. H. M. Bell and H. C. Brown, J. Amer. Chem. Soc., 88, 1473 (1966).

    Article  CAS  Google Scholar 

  16. K. Takeuchi and H. C. Brown, J. Amer. Chem. Soc., 90, 5270 (1968).

    Article  CAS  Google Scholar 

  17. H. C. Brown and H. M. Bell, J. Amer. Chem. Soc., 86, 5006, 5007 (1964).

    Google Scholar 

  18. J. A. Berson, Molecular Rearrangements, Vol. 1, P. de Mayo, Ed., Interscience, New York, 1963, Chapter 3.

    Google Scholar 

  19. M.-H. Rei and H. C. Brown, J. Amer. Chem. Soc., 88, 5335 (1966).

    Article  CAS  Google Scholar 

  20. H. L. Goering and C. B. Schewene, J. Amer. Chem. Soc., 87, 3516 (1965).

    Article  CAS  Google Scholar 

  21. S. Winstein, H. Walborsky, and K. C. Schreiber, J. Amer. Chem. Soc., 72, 5795 (1950).

    Article  CAS  Google Scholar 

  22. H. C. Brown and E. N. Peters, J. Amer. Chem. Soc., 97, 7442 (1975).

    Article  CAS  Google Scholar 

  23. H. C. Brown, E. N. Peters, and M. Ravindranathan, J. Amer. Chem. Soc., 97, 7449 (1975).

    Article  CAS  Google Scholar 

  24. H. C. Brown and G. L. Tritle, J. Amer. Chem. Soc., 90, 2689 (1968).

    Article  CAS  Google Scholar 

  25. D. V. Braddon, G. A. Wiley, J. Dirlam, and S. Winstein, J. A mer. Chem. Soc., 90, 1901 (1968).

    Article  CAS  Google Scholar 

  26. H. C. Brown, S. Ikegami, K.-T. Liu, and G. L. Tritle, J. Amer. Chem. Soc., 98, 2531 (1976).

    Article  CAS  Google Scholar 

  27. H. C. Brown and K.-T. Liu, J. Amer. Chem. Soc., 91, 5909 (1969).

    Article  CAS  Google Scholar 

  28. T. G. Traylor and C. L. Perrin, J. Amer. Chem. Soc., 88, 4934 (1966).

    Article  CAS  Google Scholar 

  29. D. Lenoir, P. v. R. Schleyer, and I. Ipaktschi, Ann., 750, 28 (1971).

    CAS  Google Scholar 

  30. H. C. Brown and G. L. Tritle, J. Amer. Chem. Soc., 88, 1320 (1966).

    Article  CAS  Google Scholar 

  31. H. C. Brown and E. N. Peters, Proc. Nat. Acad. Sci. U.S., 71,132 (1974).

    Article  CAS  Google Scholar 

  32. L. M. Stock and H. C. Brown, Adv. Phys. Org. Chem., 1, 35 (1963).

    Article  CAS  Google Scholar 

  33. H. C. Brown and K. L. Nelson, J. Amer. Chem. Soc., 75, 6292 (1953).

    Article  CAS  Google Scholar 

  34. S. Winstein, B. K. Morse, E. Grunwald, H. W. Jones, J. Corse, D. Trifan, and H. Marshall, J. Amer. Chem. Soc., 74, 1127 (1952).

    Article  CAS  Google Scholar 

  35. E. N. Peters and H. C. Brown, J. Amer. Chem. Soc., 97, 2892 (1975).

    Article  CAS  Google Scholar 

  36. S. Ikegami, D. L. Vander Jagt, and H. C. Brown, J. Amer. Chem. Soc., 90, 7124 (1968).

    Article  CAS  Google Scholar 

  37. P. D. Bartlett, G. N. Fickes, F. C. Haupt, and R. Helgeson, Accounts Chem. Res., 3, 177 (1970).

    Article  CAS  Google Scholar 

  38. M. M. Krevoy, C. R. Morgan, and R. W. Taft, Jr., J. Amer. Chem. Soc., 82, 3064 (1960).

    Article  Google Scholar 

  39. T. Tsuji, I. Moritani, and S. Nishida, Bull. Chem. Soc. Jap., 40, 2338 (1967).

    Article  CAS  Google Scholar 

  40. C. W. Jefford and W. Wojnarowski, Helv. Chim. Acta, 53, 1194 (1970)

    Article  CAS  Google Scholar 

  41. F. L. Schadt, T. W. Bentley, and P. v. R. Schleyer, J. Amer. Chem. Soc., 98, 7667 (1976).

    Article  CAS  Google Scholar 

  42. J. E. Nordlander, R. R. Gruetzmacher, W. J. Kelly, and S. P. Jindal, J. Amer. Chem. Soc., 96, 181 (1974)

    Article  CAS  Google Scholar 

  43. J. B. Lambert and G. J. Putz, J. Amer. Chem. Soc., 95, 6313 (1973).

    Article  CAS  Google Scholar 

  44. R. C. Port, Jr., R. E. Hornish, and G. A. Liang, J. Amer. Chem. Soc., 92, 7558 (1970).

    Article  Google Scholar 

  45. T. Tsuji, I. Moritani, S. Nishida, and G. Tadokoro, Bull. Chem. Soc. Japan, 40, 2344 (1967).

    Article  CAS  Google Scholar 

  46. E. N. Peters and H. C. Brown, J. A mer. Chem. Soc., 97, 7454 (1975)

    Article  CAS  Google Scholar 

  47. H. C. Brown, M. Ravindranathan, and M. M. Rho, ibid., 98, 4216 (1976).

    CAS  Google Scholar 

  48. K. Takeuchi and H. C. Brown, ibid., 90, 2693 (1968).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1977 Plenum Press, New York

About this chapter

Cite this chapter

Brown, H.C. (1977). Stabilized 2-Norbornyl Cations. In: The Nonclassical Ion Problem. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-4118-5_7

Download citation

  • DOI: https://doi.org/10.1007/978-1-4613-4118-5_7

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-4120-8

  • Online ISBN: 978-1-4613-4118-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics