Synthesis of a norbornene monomer having cyclic carbonate moiety based on CO2 fixation and its transition metal-catalyzed polymerizations

Abstract

A norbornene monomer bearing cyclic carbonate moiety (NB-CC) was successfully synthesized from the corresponding precursor having epoxy moiety by its reaction with carbon dioxide under atmospheric pressure, which was efficiently catalyzed by lithium bromide. NB-CC underwent the ring-opening metathesis polymerization (ROMP) catalyzed by a ruthenium carbene complex to give the corresponding poly(norbornene), of which side chain inherited the cyclic carbonate moiety from the monomer without any deterioration. The same ROMP system was applicable to the copolymerization of NB-CC and 5-butyl-2-norbornene (BNB), which afforded the corresponding copolymer with a composition ratio same as a feed ratio. In addition, by using a catalytic system consisted of palladium (II) acetate/tricyclohexylphosphine/triphenylcarbenium tetrakis(pentafluorophenyl)borate, the copolymerization of NB-CC and BNC proceeded successfully in a vinyl addition polymerization mode to give the corresponding poly(norbornene) having CC moiety in the side chain. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3896–3902, 2010