Polymer Bulletin

, Volume 3, Issue 4, pp 233–239 | Cite as

Anti-bredt monomers

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


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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Paper 4 in this series: H. K. HALL, Jr., and A. ELSHEKEIL: Polymer Bulletin, submitted (1980)Google Scholar
  2. J. BREDT, H. THOUET, and J. SCHMITZ: Ann., 437, 1 (1924)Google Scholar
  3. J. I. JONES: Chemistry and Industry, 1454 (1956)Google Scholar
  4. H. K. HALL, JR.: J. Am. Chem. Soc. 80, 6412 (1958)Google Scholar
  5. H. K. HALL, JR.: J. Am. Chem. Soc., 82, 1209 (1960)Google Scholar
  6. R. LUKES: Collect.Czech.Chem. Commun., 10, 148 (1939)Google Scholar
  7. R. M. SILVERSTEIN, G. C. BASSLER and T. C. MORRILL: Spectroscopic Identification of Organic Compounds, 3rd. Ed., John Wiley and Sons, Inc., New York, 1974, p. 98.Google Scholar
  8. S. SONNERSKOG: Acta Chem. Scand., 10, 467 (1956)Google Scholar
  9. H. SUMITOMO, K. HASHIMOTO: Macromolecules 10, 1327 (1971)Google Scholar
  10. H. SUMITOMO, K. HASHIMOTO, and M. ANDO: J. Polym. Sci., Polym. Lett. Ed., 11, 635 (1973)Google Scholar
  11. H. SUMITOMO and M. OKADA: Adv. Polym. Sci., 28, 48 (1978)Google Scholar
  12. J. R. WISEMAN: J. Amer. Chem. Soc., 92, 956 (1970)Google Scholar

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

Personalised recommendations