Novel Epoxynorbornane Monomers. 1. Synthesis and Characterization

The synthesis of a series of mono-, di-, and multifunctional monomers bearing the epoxynorbornane group has been carried out. Key to their preparation is the chemoselective epoxidation of 5-vinyl-2-norbornene, which affords the 5-vinyl- exo -2,3-norbornane epoxide in high yields. Monomers were prepared using this substrate and carrying out hydrosilations to make mono-, di-, tri-, and tetrafunctional epoxides. The esterification and etherification of 5-norbornene-2-methanol with succinic acid and 1,4-butanediol gives the corresponding bisnorbornene compounds, which were epoxidized to give diepoxynorbornane monomers containing ester and ether linkages. All monomers were fully characterized by means of IR and 1 H and 13 C NMR spectroscopy and by elemental analysis.