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

2012; Wiley; Volume: 51; Issue: 10 Linguagem: Inglês

10.1002/anie.201108019

1521-3773

Yuetao Zhang, Eugene Y.‐X. Chen,

Synthetic Organic Chemistry Methods

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. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.