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We synthesized several new monomers with an acid-cleavable protective group and investigated their deprotection reactions. Polymers were prepared using these monomers, and their thermal properties and dissolution rates were investigated. The acidic reactivity of protective groups of these monomers was evaluated using a method we developed. The activation energies [E a (experimental)] calculated using reaction rate constants were found to correlate to some extent with the activation energies [E a (calculated)] calculated from MOPAC. The dissolution rates of some polymers containing similar protective groups as structures were measured. The dissolution rates were related to the polarity and molecular volume (MV) of the decomposed products of protective groups.