13C NMR Chemical shifts in bicyclo[2.2.2]octanes—iii : Hydroxy acids and lactones

Abstract

A number of hydroxybicyclo[2.2.2]octane carboxylic acids and the corresponding delta lactones have been prepared, and the 13C NMR spectra show trends that, together with some deuteration experiments, provide a self consistent and unambiguous assignment of the resonance peaks. The effects produced by the substituents and the changes in chemical shifts brought about by the lactonization process are analysed.