Polymer Bulletin

, Volume 3, Issue 4, pp 233–239

Anti-bredt monomers

5. Synthesis and polymerization of 1-aza-6-oxabicyclo [3.2.1] octan-7-one
  • H. K. HallJr.
  • Ali El-Shekeil

DOI: 10.1007/BF00291963

Cite this article as:
Hall, H.K. & El-Shekeil, A. Polymer Bulletin (1980) 3: 233. doi:10.1007/BF00291963


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.

Copyright information

© Springer-Verlag 1980

Authors and Affiliations

  • H. K. HallJr.
    • 1
  • Ali El-Shekeil
    • 1
  1. 1.Department of ChemistryCollege of Liberal Arts, University of ArizonaTucsonUSA