Conjugate-Addition Organopolymerization: Rapid Production of Acrylic Bioplastics by N-Heterocyclic Carbenes


  • This work was supported by the National Science Foundation.


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It's rapid and selective: In contrast to the dimerization of α,β-unsaturated esters (acrylics) by carbene 3, the more nucleophilic carbene 2 selectively forms the single-addition product, and 1, the most nucleophilic carbene of the series, polymerizes acrylics. The biomass-derived methylene butyrolactones are quantitatively polymerized to produce medium- to high-molecular-weight bioplastics in less than one minute at ambient temperature. Mes=2,4,6-trimethylphenyl, TOF=turnover frequency.