ChemInform Abstract: Rearrangements of 1‐ and 2‐Cyano‐2‐norbornyl Cations.

Abstract

Rearrangements of 1-and 2-Cyano-2-norbornyl Cations.-2-Carbonitriles of type (I) undergo Wagner-Meerwein rearrangement in dioxane/H2O to yield 1-carbonitriles like (II) and (III). Attempts to trap norbornyl cation intermediates fail, but degenerate 6,2-H shift in the labeled nitriles (IV) and (VII) as well as in optically active nitriles is good evidence for their generation. In spiroannelated cyclopropane analogues (cf. (VIII)), a 6,2-C shift can also be observed. -(GEIER, H.; KAUTZ, C. B.; KIRMSE, W.; LANDSCHEIDT, H.; SCHIMPF, I.; SIEGFRIED, R.; Chem.