Synthesis and cyclopolymerization of 1-(2-diallylaminoethyl)pyrimidines / by Alaa Hussein Ezzeddine.

Abstract

We report in this thesis the synthesis and the polymerization of three novel monomers: 1-(2-diallylaminoethyl)uracil (DAAEU), 1-(2-diallylaminoethyl)thymine (DAAET) and 1-(2-diallylaminoethyl)cytosine (DAAEC). The synthesis of these monomers was initiated with the corresponding pyrimidine that was allowed to react with ethylene carbonate to form the hydroxyethyl adduct which in turn was chlorinated to yield the chloroethyl intermediate. Refluxing the chloroethyl intermediates with diallylamine resulted in the desired monomers. We demonstrated a two-fold increase in the overall yield of the three monomers in comparison to reported procedures. We have investigated the cyclopolymerization and cyclo-co-polymerization of all three monomers with sulfur dioxide. Whereas the cyclopolymerization of the protonated forms of both DAAEU and DAAET in water resulted in 15percent and 7percent yield respectively, the DAAEC failed to polymerize under these conditions. On the other hand, the cyclopolymerization of all three monomers with SO2 resulted in a substantial increase of polymer yield ranging from 30percent to 59percent.