Stereoelective radical copolymerization of (RS)-α-methylbenzyl vinyl ether with (S)-(-)- or (R)-(+)-N-(α-methylbenzyl)maleimide |
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Authors: | T Doiuchi H Yamaguchi |
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Institution: | Department of Chemistry, Research Institute for Atomic Energy, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558, Japan |
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Abstract: | Racemic α-methylbenzyl vinyl ether was copolymerized with optically active (S)-(-)- or (R)-(+)-N-(α-methylbenzyl)maleimide using 2,2′-azobisisobutyronitrile in order to examine the possibility of stereoelective radical polymerization of vinyl-type racemic monomers. The resulting copolymers were found to have almost alternating sequences of the two kinds of monomeric units. The non-polymerized α-methylbenzyl vinyl ether, recovered from the copolymerization system, showed an optical activity of opposite sign to the optically active comonomer used, indicating clearly that the co-polymerization process is stereoelective. It was confirmed that α-methylbenzyl vinyl ether preferentially incorporated in the copolymer has the same absolute configuration as the optically active N-substituted maleimide. |
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