Synthesis of a Divinyl-functionalized Diamantane-Analogue from naturally occurring myo-Inositol and its application to polymer synthesis via the Thiol-ene reaction

Highlights

• -Myo-inositol obtained from rice bran was transformed into a divinyl derivative.

• -The divinyl derivative bears a rigid hexaoxadiamantane core.

• -The divinyl compound underwent radical polyaddition with dithiols, giving semi-crystalline polythioethers.

• -The divinyl compound was transformed into a diol, which was useful for polyurethane synthesis.

Abstract

Myo-inositol, a naturally occurring cyclic compound obtained from rice bran, was transformed into a divinyl derivative bearing a rigid hexaoxadiamantane (HODAM) core composed of two orthoester moieties. The divinyl compound underwent radical polyaddition with dithiols to afford the corresponding semi-crystalline polythioethers, the melting temperatures (T_m) of which were above 240 °C. Furthermore, the divinyl compound was transformed into a HODAM-bearing diol via the radical addition of 2-mercaptoethanol to the vinyl groups. The diol product was used as a rigid monomer in polyurethane synthesis. The obtained polyurethanes exhibited glass transition temperatures (T_g) ranging from 55 to 110 °C.