Synthesis of Novel 5-Toluenesulfonyl- and 5-Methylsulfonylcyclooctene Polymers and Their Cоpolymers with Cyclooctene

Abstract

This work addresses the development of methods for the synthesis of novel functional polymers from cyclooctene. Novel monomers containing toluenesulfonyl (tosyl) or methylsulfonyl (mesyl) groups in position 5, which are easily involved in the reaction of bimolecular nucleophilic substitution, are obtained. Novel homopolymers poly(5-toluenesulfonylcyclooctene) and poly(5-methylsulfonylcyclooctene) are synthesized by ring-opening metathesis polymerization mediated by Grubbs’s catalysts and characterized by NMR, GPC, and DSC methods. Multiblock copolymers with isolated functional groups are synthesized by interchain exchange cross-metathesis between polycyclooctene and poly(5-toluenesulfonylcyclooctene), and statistical copolymers are synthesized by the metathesis copolymerization of cyclooctene and 5-toluenesulfonyl- or 5-methylsulfonylcyclooctene. A procedure for grafting ethylene glycol and its monosubstituted derivatives onto poly(5-methylsulfonylcyclooctene) and poly(5-methylsulfonylcyclooctene) is developed and tested. This modification procedure renders it possible to reach a low degree of grafting due to the competing elimination of tosyl and mesyl functional groups leading to the formation of additional double carbon bonds in the polymer backbone.