Communication

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

  1. Dr. Yuetao Zhang,
  2. Prof. Dr. Eugene Y.-X. Chen*

Article first published online: 23 JAN 2012

DOI: 10.1002/anie.201108019

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 10, pages 2465–2469, March 5, 2012

Additional Information

How to Cite

Zhang, Y. and Chen, E. Y.-X. (2012), Conjugate-Addition Organopolymerization: Rapid Production of Acrylic Bioplastics by N-Heterocyclic Carbenes. Angew. Chem. Int. Ed., 51: 2465–2469. doi: 10.1002/anie.201108019

Author Information

  1. Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872 (USA)

*Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872 (USA)

  1. †

    This work was supported by the National Science Foundation.

Publication History

  1. Issue published online: 1 MAR 2012
  2. Article first published online: 23 JAN 2012
  3. Manuscript Received: 14 NOV 2011

Funded by

  • National Science Foundation

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Keywords:

  • N-heterocyclic carbenes;
  • organocatalysis;
  • polymerization;
  • polymers;
  • renewable resources
Thumbnail image of graphical abstract

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.

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