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for the case where the starting monomer mixture is racemic, that is, R 0 S 0 .
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Asymmetric Induction
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A special case of asymmetric enantiomer-differentiating polymerization is the isoselective copolymerization of optically active 3-methyl-1-pentene with racemic 3,7-dimethyl-1-octene by TiCl4 and diisobutylzinc [Ciardelli et al., 1969]. The copolymer is optically active with respect to both comonomer units as the incorporated optically active 3-methyl-1-pentene directs the preferential entry of only one enantiomer of the racemic monomer. The directing effect of a chiral center in one monomer unit on the second monomer, referred to as asymmetric induction, is also observed in radical and ionic copolymerizations. The radical copolymerization of optically active a-methylbenzyl methacrylate with maleic anhydride yields a copolymer that is optically active even after hydrolytic cleavage of the optically active a-methylbenzyl group from the polymer [Kurokawa and Minoura, 1979]. Similar results were obtained in the copolymerizations of mono- and di-l-menthyl fumarate and ( )-3-(b-styryloxy)menthane with styrene [Kurokawa et al., 1982].
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The stereochemistry of ring-opening polymerizations has been studied for epoxides, episul des, lactones, cycloalkenes (Sec. 8-6a), and other cyclic monomers [Pasquon et al., 1989; Tsuruta and Kawakami, 1989]. Epoxides have been studied more than any other type of monomer. A chiral cyclic monomer such as propylene oxide is capable of yielding stereoregular polymers. Polymerization of either of the two pure enantiomers yields the isotactic polymer when the reaction proceeds in a regioselective manner with bond cleavage at bond 1.
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This is generally the case for the typical polymerization of epoxides as well as other cyclic monomers, although the regioselectivity is not 100%. The degree of isoselectivity is generally decreased in proportion to the extent of ring opening at bond 2. There are no initiator systems that are even moderately isoselective subsequent to bond cleavage at bond 2. The extent of regioselectivity at bond 1 is greater than 90% for many anionic polymerizations. It is very dif cult to give a generalization that holds up well in this respect. In a number of polymerizations signi cant amounts of cleavage at bond 2 have been reported, such as propylene oxide polymerizations by Zn(C2 H5 )2 or Al(C2 H5 )3 with H2 O or Zn(C2 H5 )2 with CH3 OH, and styrene oxide polymerization by aluminum isopropoxide [Tsuruta and Kawakami, 1989]. The extent of regioselectivity depends markedly on reaction conditions in some systems. Thus, polymerization by Zn(C2 H5 )2 /H2 O proceeds exclusively by cleavage at bond 1 in many polymerizations but signi cant extents of cleavage occur at bond 2 in other polymerizations with the differences depending on the relative amounts of Zn(C2 H5 )2 and H2 O. Cationic polymerizations of epoxides are signi cantly less regioselective and isoselective compared to anionic polymerizations. Polymerization of racemic propylene oxide proceeds differently depending on the initiator. Polymerization by potassium hydroxide or alkoxide proceeds with better than 95% regioselectivity of cleavage at bond 1, but the product is atactic [Tsuruta and Kawakami, 1989]. Both (R)- and (S)-propylene oxide react at the same rate as shown by the invariance
STEREOCHEMISTRY OF POLYMERIZATION
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of the optical rotation of unreacted monomer with conversion in a polymerization where the initial ratio of the two enantiomers was unequal. The atacticity of the product indicates that the initiator is unable to distinguish between the R and S enantiomers of propylene oxide and both enantiomers react at the same rate with complete cross-propagation. Polymerizations by Zn(OCH3 )2 and a, b, g, d-tetraphenylporphyrin (structure VI in Sec. 7-2a-1) proceed in a completely regioselective manner (cleavage at bond 1), but with only modest isoselectivity (67% and 68% isotactic dyads, respectively) [Le Borgne et al., 1988; Tsuruta, 1981]. For polymerization by a, b, g, d-tetraphenylprophyrin, the degree of isotacticity varied with the ratio of (R)- and (S)-propylene oxide in the feed. Polymerization proceeds as an asymmetric enantiomer-differentiating polymerization but with signi cant cross-propagation. The highest isoselectivity reported, (mm) 0.81, for a propylene oxide polymerization was achieved with an initiator derived from dialkylzinc and methanol [Hasebe and Tsuruta, 1988; Tsurata, 1986; Tsuruta and Kawakami, 1989; Yoshino et al., 1988]. The stereochemistry of ring-opening polymerizations of episul des, lactones, lactides, N-carboxy-a-amino acid anhydrides, and other monomers has been studied but not as extensively as the epoxides [Boucard et al., 2001; Chatani et al., 1979; Duda and Penczek, 2001; Elias et al., 1975; Guerin et al., 1980; Hall and Padias, 2003; Imanishi and Hashimoto, 1979; Inoue, 1976; Ovitt and Coates, 2000; Spassky et al., 1978; Zhang et al., 1990].
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