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

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 (Tm) 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 (Tg) ranging from 55 to 110 °C.

Keywords

• Myo-inositol
• Diamantane
• Divinyl compound
• Thiol-ene reaction
• Polyaddition