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Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization

submitted on 21.02.2020, 23:17 and posted on 24.02.2020, 12:20 by Sepand Nistanaki, Hosea Nelson
We report the utility of readily available heterocycles as precursors to unique ring-opening metathesis polymerization (ROMP) monomers. Photochemical valence isomerization reactions of pyridones, dihydropyridines, and pyrones dearomatize the parent heterocycles to their highly strained Dewar isomers, which readily engage in controlled ROMP reactions using Grubbs catalysts. This strategy is used to access novel polymer backbones that contain strained β-lactam and azetidine cores, which can be further derivatized using post-polymerization chemistries. We demonstrate this through the synthesis of water-soluble β-amino acid polymers and soluble poly(acetylene) derivatives.


Email Address of Submitting Author


University of California, Los Angeles


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest.