Properties and methods of synthesis of several optically active polyoxiranes and polythiiranes

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Abstract
Optically active oxiranes and thiiranes are prepared from the corresponding asymmetric 1,2‐diols or by means of stereoelective polymerization.The properties of polymers prepared from chiral monomers by polymerization with anionic, cationic, and stereospecific initiators are compared. In the latter case, the stereospecificity depends not only on the nature of the monomer but also on its enantiomeric distribution. The direction of ring opening could be easily followed when using optically active monomers and there are satisfactory correlations with other methods such as ozonolysis or NMR spectroscopy. In some cases properties of optically active and racemic polymers are different, this enables their separation by physical methods. Chiroptical properties of monomers and polymers having thioether chromophores are given. The stereoregularity of the polymers determined by NMR spectroscopy may be correlated and substantiated by calculations of enantiomeric distribution from optical activity. Optical activity is, therefore, a useful tool for studying the mechanistic aspects of polymerization and the properties of the obtained products.

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