Synthesis of High-T-g Polymers via ROMP of Oxanorbornene Dicarboximides with Halogen Groups

Abstract

This paper describes the synthesis of exo-N-phenyl-7-oxanorbornene-5, 6-dicarboximides with different substituents at para positions in the aromatic ring and their polymerization by ring-opening metathesis polymerization (ROMP) leading to high-T-g polymers. Exo-N-4-chlorophenyl-7-oxanorbornene-5,6-dicarboximide (ClPhONDI, 3a), exo-N-4-bromophenyl-7-oxanorbornene-5,6-dicarboximide (BrPhONDI, 3b), and exo-N-4-iodophenyl-7-oxanorbomene-5,6-dicarboximide (1PhONDI, 3c) monomers were synthesized. Polynorbornene dicarboximides were obtained via ROMP using a first-generation ruthenium alkylidene catalyst, Cl-2(PCy3)(2)Ru(=CHPh). The resulting amorphous polymers with trans configuration of the double bonds were characterized by NMR, SEM, DSC, and GPC. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:36-43, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20576