Isolation and cationic ring-opening polymerization of 2,3,5,6-tetrahydroimidazo[2,1-b][1,3]oxazole to produce a thermally stable polyurea

A bicyclic pseudourea, 2,3,5,6-tetrahydroimidazo2,1-b]1,3]oxazole ( 1 ), was isolated for the first time, and its cationic and spontaneous polymerizations were examined. Both polymerizations gave poly(1,3-imidazolidin-2-one-1,3-diylethylene) ( 2 ) in high yields. The polymer is a crystalline solid with glass transition and melting temperature of 51°C and 286°C, respectively. Thermogravimetry showed that it is stable up to 450°C under nitrogen.