Organic Chemistry

Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization

Authors

Abstract

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.

Content

Thumbnail image of Dewar heterocycle polymers manuscriptSKN - ChemRxiv.pdf

Supplementary material

Thumbnail image of Dewar heterocycle polymer paper supporting information SKN.pdf
Dewar heterocycle polymer paper supporting information SKN