Rearrangement of a Bicyclic System to a Bicyclic System. Nonclassical Ions

Article abstract of DOI:10.1021/jo00266a004

The syntheses and the establishment of the absolute configurations of chiral (S)-(+)-2-bromodibenzobicyclo<2.2.2>octadiene-2-carboxylic acid (1) and (1S,2S,5S)-(-)-exo-2-methoxydibenzobicyclo<3.2.1>octadiene-1-carboxylic acid (2) and their derivatives are described.The rearrangement of 1 to 2 is discussed in terms of a nonclassical ion intermediate in light of the observed stereochemistry.