Equilibrating Tertiary 2-Norbornyl Cations
The 1,2-di-p-anisyl-2-norbornyl cation is a particularly fascinating species with special historic interest. It is the first 2-norbornyl cation to be clearly characterized as a classical ion. It is also the first member to be investigated of a highly informative group of tertiary 2-norbornyl cations capable of existing either as a symmetrical σ-bridged nonclassical ion or as a pair of rapidly equilibrating classical ions. The experimental results clearly established the 1,2-di-p-anisyl-2-norbornyl cation to be the latter. The discovery was made by the individual who is still one of the leading exponents of σ-bridged cations. It must have been a heart-rending experience.
KeywordsCanonical Structure Classical Cation Resonance Hybrid Endo Isomer Bridgehead Proton
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