Novel Epoxynorbornane Monomers. 1. Synthesis and Characterization

Abstract

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 1H and 13C NMR spectroscopy and by elemental analysis.