Development of “Triepoxides” with a Rigid Framework Derived from myo-Inositol

Abstract

Using myo-inositol, a component of rice bran, as a starting material, we synthesized a series of triepoxide possessing an adamantane-like rigid orthoester framework. Orthoester derivatives of myo-inositol bearing different substituents at the bridgehead position were prepared, and their three hydroxy groups were allylated. Subsequent epoxidation of the carbon–carbon double bonds of the allyl groups afforded the target triepoxides. Network polymers were obtained by polyaddition reactions of the resulting triepoxides with various diamines, followed by thermogravimetric analysis and differential scanning calorimetry. The results revealed that increasing the bulkiness of the bridgehead substituents led to a decrease in both decomposition temperature and glass transition temperature.