Synthesis of New Aprotic Polar Polymers

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N, N-Dimethylacetamide (DMAc), dimethyl sulfoxide (DMSO), and hexamethyl-phosphoric triamide (HMPA) are unique and useful aprotic polar solvents in organic synthesis. In this research project, the polymer homologues of these polar solvents were synthesized.First, the polymer homologue of DMSO was prepared. Aliphatic polysulfoxides were successfully synthesized from the corresponding aliphatic polysulfides by the oxidation using hydrogen peroxide. The polysulfoxides obtained were used as oxidizing reagents in Swern oxidation. A real polymer homologue of DMSO, poly-(ethylene sulfoxide) was prepared by selective oxidation of poly (ethylene sulfide).The poly (HMPA) was synthesized by the polymer reaction of linear poly (ethyleneimine) with bis (dimethylamino) phosphoryl chloride in the presence of DBU.The poly (HMPA) obtained showed good miscibility with commodity polymers such as polystyrene. The poly (HMPA) was also prepared by ring-opening polymerization of bis (dimethylamino) phosphorylpropylenimine.As an example of poly (DMAc), poly (N, N-dimethylcarbamoylmethylene) having amide groups on all main chain carbons was successfully prepared by the polymer reaction of poly (fumaric acid).