Synthesis and structure of poly(oxazolidine-acetals). 2. Polycondensation of terephthaldehyde with 2-amino-2-hydroxymethyl-1,3-propanediol

In the reaction of terephthaldehyde 1 or o-phthaldehyde 1a with 2-amino-2-hydroxymethyl-1,3-propanediol 2, ring-chain tautomeric mixtures were formed. At higher temperature in the presence of acidic catalysts (TsOH, PVP-TsOH complex), these multicomponent tautomeric equilibria were shifted to bis-oxazolidine 4, which polycondensates to poly(oxazolidine-acetals) 6. The structure of the polymer was studied by NMR spectroscopy. The reactivity of the oxazolidine ring system was determined by alkylation with alkyl iodide and acylation with acetic anhydride.