Syntheses and reactions of functional polymers. XLVI. Preparation and reactions of N‐benzyloxyisomaleimide–styrene copolymer

Abstract
Polymerization of N‐benzyloxymaleimide(I) was attempted to obtain a polymer with the N‐hydroxysuccinimide unit in the chain. In the light of infrared and NMR data the compound reported by Ames as N‐benzyloxymaleimide is N‐benzyloxyisomaleimide (III). Homopolymerization of III did not give polymer. Copolymerization of III with styrene was carried out in dioxane at 70°C. A strong alternation tendency like that of maleimides was observed. Monomer reactivity ratios and Q‐e values were determined. Copolymer having the isoimide structure showed infrared absorptions at 1815 and 1675 cm−1 in the carbonyl region. The copolymer was isomerized to N‐benzyloxymaleimide type copolymer and debenzylated to N‐hydroxymaleimide type copolymer. An insoluble copolymer was prepared by using divinylbenzene as a crosslinking agent and was converted to N‐acetoxymaleimide type copolymer, which was used as an insoluble acetylating agent.

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