A series of N-(substituted phenyl) maleimides was synthesized and their free radical chain polymerization examined. Polymerization of the N-(hydroxyphenyl) maleimides in DMF gave typically very low molecular weight polymers. Masking the phenolic functionality with an acetoxy group gave marginally higher molecular weights. Protection using a tetrahydropyranyl (THP) substituent gave a similar polymerization pattern to acetoxy. However, the THP protected monomers had increased solubility in non-polar solvents such as benzene, and when polymerized in this solvent gave very much higher molecular weight polymers. The reactivity of the maleimide monomers was also found to be dependent on the substitution pattern of the phenyl ring, with substituents in the ortho position tending to lower the molecular weight of the polymer formed. The THP substituent was readily removed to yield poly(N-(hydroxyphenyl) maleimides). The polymers were found to exhibit excellent thermal stability.