Concepedia

Destabilized 2‐Norbornyl Cations

Wolfgang Kirmse, Uwe Mrotzeck, Rainer Siegfried

Angewandte Chemie International Edition in English · 1985 · 17 citations · 12 references

DOI

Concepts

Abstract

Four acceptor substituents at C-5 and C-6 destabilize the non-classical structure of the 2-norbornyl cation. The Wagner-Meerwein rearrangement of 1 to 2 is completely forestalled by such a substitution pattern; however, 1 undergoes an exo, exo-3,2-H shift to give 3.

References

12

Orbital mixing rule

Satoshi Inagaki, Hiroshi Fujimoto, Kenichi Fukui · Journal of the American Chemical Society · 1976 · 234 citations

, , +5

Conclusion of the classical-nonclassical ion controversy based on the structural study of the 2-norbornyl cation

George A. Olah, G. K. Surya Prakash, Martin Saunders · Accounts of Chemical Research · 1983 · 146 citations

, , +8

Electron-deficient carbocations

Paul G. Gassman, Thomas T. Tidwell · Accounts of Chemical Research · 1983 · 113 citations

, , +5

Inductivity and bridging in carbocations

C. A. Grob · Accounts of Chemical Research · 1983 · 110 citations

, , +5

The energy of the transition states and the intermediate cation in the ionization of 2-norbornyl derivatives. Where is the nonclassical stabilization energy?

Herbert C. Brown · Accounts of Chemical Research · 1983 · 105 citations

, , +7