Studies of reaction pathways by X-ray crystallography: a spectroscopic, crystallographic, and theoretical (ab initio) investigation of 6-oxobicyclo[2.2.1 ]heptane-endo-2-carboxylic acid

Abstract

I.r. and n.m.r. spectroscopic evidence shows that the title compound (a norbornane derivative) exists, in solution, as a mixture of ‘open’(γ-keto-acid) and ‘closed’(hydroxylactone) forms separated by a low energy barrier. The structural differences between the norbornane and analogous cis- and trans-decalin keto-acids are discussed in terms of trajectory differences for ring closure: the results of calculations are presented in support of this.