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A new mode of polymerization of glycidyl acetate ( 1a ) to yield a poly(ortho ester), i.e., poly(2-methyl-1,3-dioxolane-4,2-diyl)oxymethylene ( 3a ), was explored. This new polymerization exclusively proceeded when a bulky Lewis acid, methylaluminium bis(2,6-di- tert -butyl-4-methylphenoxide) ( 2a ), was employed as the catalyst. The polymerization of 1a with 4 mol % of 2a proceeded smoothly in toluene at 0 °C and gave 3a in 82% after 1 h. The time-trace of the polymerization system revealed that this polymerization was completed within 3 min under these conditions. The polymerization mechanism is tentatively assumed as polyaddition of zwitterionic species produced from 1a with the assistance of 2a . The polymerization of glycidyl methacrylate ( 1b ) with 2a gave poly(ortho ester) 3b in a similar manner.
Miyamoto et al. (1997) studied this question.