Synthesis and characterization of dimethyl cubane-1, 4-dicarboxylate

By using cyclopent-2-enone as starting material, dimethyl cubane-1, 4-dicarboxylate was synthesized with total yield of 0.7% and purity of 99% via substitution, addition, elimination, Diels-Alder reaction, cycloaddition, Favorskii rearrangement and esterification. The catalyst of esterification was strong acidic cation exchange resin. With the catalyst loading of 2%, it could be used repeatedly three times. The structure of dimethyl cubane-1, 4-dicarboxylate and dicyclopentadienone were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analysis.