Poly(vinyl acetate) and its copolymers represent an important class of commodity polymers. However, the preparation of copolymers of vinyl acetate (VAc) and more activated monomers (MAMs) <i>via</i> copolymerization is greatly restricted due to their disparate reactivities. Issues relating to reactivity ratios remain a fundamental challenge in copolymerization. Herein, we describe a post-polymerization modification approach using poly(methyl vinyl ketone-<i>co</i>-MAM)s as substrates to access synthetically challenging poly(VAc-<i>co</i>-MAM)s. Although the direct translations of existing small-molecule Baeyer-Villiger (BV) protocols into a post-polymerization modification method failed, a mechanism-guided multi-parameter optimization on polymer substrates disclosed a set of unique “exhaustive” BV protocols which enabled a nearly quantitative functionalization without obvious chain scission or cross-linking. Furthermore, a one-pot copolymerization/“exhaustive” BV post-modification procedure was developed to produce such copolymers in a convenient and scalable manner. This user-friendly methodology is able to access diverse poly(VAc-<i>co</i>-MAM)s including both statistical and narrow-dispersed block copolymers and could greatly facilitate the exploration of applications with such materials.
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