1,4-DIMETHYLBICYCLO[2.2.1]HEPTANE DERIVATIVES

The product from the action of methylmagnesium iodide on bicyclo[2.2.1]heptane-2,5-dione gave 2-exo-5-endo-diacetoxy-1,4-dimethylbicyclo[2.2.1]heptane on treatment with sulfuric acid in acetic acid. This has been converted to 1,4-dimethylbicyclo[2.2.1]heptane-2-exo-5-endo-diol, to 1,4-dimethylbicyclo[2.2.1]heptane-2,5-dione, and to 1,4-dimethylbicyclo[2.2.1]heptane-2-endo-5-endo-diol. The stereochemical assignments have been made on the basis of the interpretation of the nuclear magnetic resonance spectra of these compounds. The exo–endo diacetoxy compound is shown to be the expected product from a double Wagner–Meerwein rearrangement.