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Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization

preprint
submitted on 21.02.2020 and posted on 24.02.2020 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.

History

Email Address of Submitting Author

snistanaki@chem.ucla.edu

Institution

University of California, Los Angeles

Country

United States

ORCID For Submitting Author

0000-0002-5252-803X

Declaration of Conflict of Interest

No conflict of interest.

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