Ring-opening polymerization of atom-bridged and bond-bridged bicyclic ethers, acetals and orthoesters

  • Y. Yokoyama
  • H. K. HallJr.
Conference paper
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Part of the Advances in Polymer Science book series (POLYMER, volume 42)

Abstract

During these two decades, the polymerization of bicyclic compounds has been studied to obtain basic knowledge on ring-opening polymerization and for industrial and biomedical applications. In 1961, Korshak et al.1) reported the stereospecific polymerization of 1,6-anhydro-2,3,4-tri-O-methyl-D-glucopyranose. Schuerch and coworkers2–3) have developed the chemical synthesis of polysaccharides of biomedical interest. Very recently, Sumitomo and Okada4) reviewed the reaction mechanism of the ring-opening polymerization and the structures and properties of the resulting polymers of bicyclic acetals, bicyclic oxalactones, bicyclic oxalactams, and related heterobicyclo compounds. Tadokoro5, 6) reported the structure of crystalline polymers by X-ray diffraction, infrared, Raman spectroscopy, and energy calculations. Many workers7) have studied the structure of oxygen-containing polymers in solution. Finally, the anomeric effect and gauche effect have been made clear by many workers8, 9).

Therefore, we hope to discuss the polymerization mechanism and polymerizability of bicyclic compounds containing oxygen atoms and their relation to the monomer and polymer structures. Finally, some biomedical application of polymers will be mentioned.

The review will be limited to atom- and bond-bridged bicyclic monomers. The important work of Bailey on the polymerization of spiro bicyclo orthoesters and spiro bicyclic orthocarbonates has been adequately described elsewhere10a–d, 60–63). The outstanding and systematic body of work by Schuerch2, 3) and others on the ring opening polymerization of bicyclic acetals derived from carbohydrate precursors will also not be covered here.

Keywords

Anomeric Effect Cyclohexane Ring Polymerization Mechanism Ring Strain Bicyclic Compound 
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Copyright information

© Springer-Verlag 1982

Authors and Affiliations

  • Y. Yokoyama
    • 1
  • H. K. HallJr.
    • 1
  1. 1.Department of Chemistry, College of Liberal ArtsUniversity of ArizonaTucsonUSA

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