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Anti-bredt monomers

5. Synthesis and polymerization of 1-aza-6-oxabicyclo [3.2.1] octan-7-one

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Summary

1-Aza-6-oxabicyclo [3.2.1]octan-7-one 3 polymerized in bulk to polyurethane at 112–131°C with opening of the 5-membered urethane ring. Organometallic, cationic, anionic and organophosphoric initiators polymerized the strained bicyclic urethane to the polyurethane. In solution the monomer was shown to polymerize slowly under the influence of phosphoric acid. The driving force for the polymerization may be the relief of strain energy in the monomer caused by a boat conformation of the 6-membered ring.

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References

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Hall, H.K., El-Shekeil, A. Anti-bredt monomers. Polymer Bulletin 3, 233–239 (1980). https://doi.org/10.1007/BF00291963

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Keywords

  • Polymer
  • Polyurethane
  • Phosphoric Acid
  • Material Processing
  • Urethane