Methods were sought for the synthesis of thermally stable, oil resistant elastomers based on chains containing aromatic heterocyclic rings. Three 1,3-dipole presursors, the sydnone, the hydrazide chloride, and the tetrazole systems were studied in terms of their usefulness as monomers for 1,3- dipolar addition reactions. Of the three, only the tetrazoles show promise as useful monomers. A series of polymers which possessed moderate viscosities, high thermal stabilities, and high polarity was generated via the 1,3-doplar addition reaction. In general, the polymers showed high second-order transition temperatures and efforts to decrease the transition temperature by incorporating flexible linkages into the polymer were unsuccessful. Methods of synthesis and characterization of monomers, model compounds, and polymers are described.