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Meerwein and equilibrating carbocations

  • Herbert C. Brown
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 80)

Abstract

Fifty-seven years ago, Hans Meerwein published a paper, “über die Gleichgewichts-Isomerie zwischen Bornylchlorid, Isobornylchlorid and Camphenchlorhydrat 1)”, which had immense consequences for the development of physical organic chemistry. The paper contains the first proposal of carbonium ions as intermediates in molecular rearrangements. It also provided the basis for the later proposal of a nonclassical ion as an intermediate2, in place of the pair of rapidly equilibrating classical cations utilized by Meerwein1). Consequently, this publication opened the door to major research efforts by numerous chemists throughout the world. It is the purpose of this review to discuss the question of whether it is the Meerwein concept of equilibrating cations or the Wilson proposal of a mesomeric nonclassical cation that best accounts for the fascinating behavior of 2-norbornyl cations.

Keywords

Classical Cation Kcal Tool Steric Strain Bornyl Acetate Alkyl Chloride 
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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Copyright information

© Springer-Verlag 1979

Authors and Affiliations

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

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