Bicyclic functionalized methacrylates were synthesized by a Diels-Alder reaction of furfuryl methacrylate with maleic anhydride and subsequent conversion to the corresponding monomers containing carboxylic groups. The structure of the bicyclic functionalized methacrylates was confirmed by elemental analysis, IR, H-1 NMR and C-13 NMR spectroscopy. The radical photopolymerization of bicyclic monomethacrylates in dimethylformamide with 2,2＇-azobisisobutyronitrile (AIBN) resulted in soluble polymers while a bicyclic dimethacrylate resulted in a crosslinked polymer.