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High molecular weight, soluble poly(p-hydroxy-a-methylstyrene) has been synthesized for the first time by cationic polymerization of p-[(fert-butoxycarbonyl)oxy]-«-methylstyrene with boron trifluoride etherate as an initiator in liquid sulfur dioxide followed by thermolytic deprotection. Cationic polymerization of p-acetoxy-a-methylstyrene in dichloromethane followed by hydrazinolysis afforded the title compound, but the polymerization was accompanied by partial cleavage of the protecting group. Conventional cationic polymerization of p-[ (tert-butoxycarbonyl) oxy] --methylstyrene in dichloromethane resulted in formation of low molecular weight polymer accompanied by partial cleavage of the protecting group. Ether monomers, such as p-methoxy-and p-(ethoxymethoxy)-a-methylstyrenes, readily underwent cationic polymerization, while the p-(2-methoxyethoxy)methyl derivative suffered from partial deprotection and cross-linking. Removal of the ether protecting group was, in all cases, accompanied by chain degradation and/or cross-linking. Chemical modification of poly(a-methylstyrene) and poly(p-bromo-«-methylstyrene) by lithiation followed by hydroxylation produced cross-linked materials.

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