Preparation and oxidation with chromic acid of all six 3-bromo-5-hydroxy- and -5-oxo-bicyclo[2.2.1]heptane-2,6-carbolactones

Abstract

The title compounds have been prepared and their rates of oxidation with chromic acid determined. endo-Hydroxy(3) are oxidised faster than exo-hydroxy-compounds (1). Strain in the product is therefore unlikely to be a rate-determining factor. The 3-exo-bromo-ketone (2a) forms a stable hydrate (4) and is oxidised faster than the 3-exo-bromo-5-exo-alcohol (1a). The stable 3-endo-bromo-ketone (2b) is oxidised more slowly than the 3-endo-bromo-alcohols (1b) and (3b). Compounds with a 3-endo-bromo-substituent [(1b), (2b), and (3b)] showed analgetic activity.