Final Comments

  • Herbert C. Brown


It has long been recognized that saturated structures with electron-deficient cationic centers are highly reactive species, undergoing both rapid rearrangements and rapid reactions with external nucleophiles.1,2 Such an electron-deficient cationic center will undertake to reduce its electron deficiency by internal electron shifts, delocalizing the charge throughout the carbon structure, or by interacting with the solvent or other nucleophiles in its vicinity.


Final Comment Phenyl Substitution Phlogiston Theory Saturated Structure Rapid Rearrangement 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    H. Meerwein and K. van Emster, Ber., 55, 2500 (1922).Google Scholar
  2. 2.
    F. C. Whitmore, Chem. Eng. News, 26, 668 (1948).CrossRefGoogle Scholar
  3. 3.
    J. D. Roberts and R. H. Mazur, J. Amer. Chem. Soc., 73, 3542 (1951).CrossRefGoogle Scholar
  4. 4.
    S. Winstein and D. Trifan, J. Amer. Chem. Soc., 74, 1147, 1154 (1952).CrossRefGoogle Scholar
  5. 5.
    J. D. Roberts and J. A. Yancy, J. Amer. Chem. Soc., 74, 5943 (1952).CrossRefGoogle Scholar
  6. 6.
    H. C. Brown and R. S. Fletcher, J. Amer. Chem. Soc., 71, 1845 (1949).CrossRefGoogle Scholar
  7. 7.
    H. C. Brown and H. Berneis, J. Amer. Chem. Soc., 75, 10 (1953).CrossRefGoogle Scholar
  8. 8.
    F. Brown, E. D. Hughes, C. K. Ingold, and J. F. Smith, Nature, 168, 65 (1951).CrossRefGoogle Scholar
  9. 9.
    P. D. Bartlett, J. Chem. Educ., 30, 22 (1953).CrossRefGoogle Scholar
  10. 10.
    R. Heck and V. Prelog, Helv. Chim. Acta, 38,1541 (1955).CrossRefGoogle Scholar
  11. 11.
    H. C. Brown and F. J. Chloupek, J. Amer. Chem. Soc., 85, 2322 (1963).CrossRefGoogle Scholar
  12. 12.
    P. D. Bartlett and T. T. Tidwell, J. Amer. Chem. Soc., 90, 4421 (1968).CrossRefGoogle Scholar
  13. 13.
    V. Prelog, Rec. Chem. Progr., 18, 247 (1957).Google Scholar
  14. 14.
    P. D. Bartlett, Nonclassical Ions, Benjamin, New York (1965).Google Scholar
  15. 15.
    R. S. Mulliken, C. A. Rieke, and W. G. Brown, J. Amer. Chem. Soc., 63, 41 (1941).CrossRefGoogle Scholar
  16. 16.
    A. E. Remick, Electronic Interpretations of Organic Chemistry, Wiley, New York, 1943.Google Scholar
  17. 17.
    H. C. Brown, “The Transition State,” Chem. Soc. (London), Spec. Publ., 16, pp. 140–158, 174–178 (1962).Google Scholar
  18. 18.
    H. C. Brown, Chem. Eng. News, 45, 86, Feb. 13, 1967.CrossRefGoogle Scholar
  19. 20.
    R. B. Woodward, Perspective in Organihemistry, A. Todd, Ed., Interscience, New York, 1956, pp.177–178.Google Scholar
  20. 21.
    P. Hartog, Memorial Lectures, The Chemical Society (London), 4, 21 (1951).Google Scholar
  21. 23.
    For a review, see G. A. Olah, Carbocations and Electrophilic Reactions, Wiley, New York, 1974.Google Scholar
  22. 24.
    Review: L. Radom, D. Poppinger, and R. C. Haddon, Carbonium Ions, Vol. V, Chap. 38, pp.Google Scholar
  23. For a review, G. A. Olah and P. v. R. Schleyer, Eds., Wiley-Interscience, New York, 1976.Google Scholar
  24. 25.
    Review: M. Sundaralingam and A. K. Chwang, Carbonium Ions, va. V, Chap. 39, pp. 2427ff, G. A. Olah and P. v. R. Schleyer, Eds., Wiley-Interscience, New York, 1976.Google Scholar

Copyright information

© Plenum Press, New York 1977

Authors and Affiliations

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

Personalised recommendations