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8-4f Mechanism of Syndioselective Propagation The synthesis of syndiotactic polymers by Ziegler Natta initiators has been successful for propone, styrene, and some 1,3-dienes [Hagen et al, 2002; Pasquon et al, 1989; Youngman and Boor, 1967; Zambelli et al, 2001] Only soluble initiators, almost exclusively limited to vanadium compounds, yield highly syndioselective polymerization The level of syndiotacticity is not as high as the isotacticity achieved with the heterogeneous titanium aluminum initiator systems The maximum syndiotacticity, rr 0:9, is achieved only at low temperatures ( 78 C) (Metallocene initiators produce more highly syndioselective polymerizations Sec 8-5) The initiator formed from VCl4 and Al(C2 H5 )2 Cl is one of the most ef cient means for syndioselective polymerization of propene, especially in the presence of a Lewis base such as anisole (methoxybenzene) [Doi, 1979a,b; Natta et al, 1962; Zambelli et al, 1978, 1980].

Other vanadium compounds such as vanadium acetylacetonate and various vanadates [VO(OR)x Cl 3 x , where x 1,2,3] can be used in place of VCl4 but are more limited in their stereoselectivity [Doi et al, 1979] Trialkylaluminum can also be used as a coinitiator, but only for VCl4 Syndiotacticity increases with decreasing temperature; most of these syndioselective polymerizations are carried out below 40 C and usually at 78 C The initiators must be prepared and used at low temperatures since most of them undergo decomposition at ambient and higher temperatures There is considerable reduction of V(III) to V(II) with precipitation of ill-de ned products that are low in activity and do not produce syndiotactic polymer, when the initiators are prepared at or warmed to temperatures above ambient The driving force for syndiotactic placement with Ziegler Natta initiators is similar to that (Sec.

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8-3) for low-temperature radical and ionic, noncoordinated polymerizations the repulsive interaction between substituents of the terminal unit of the propagating chain and incoming monomer This is the polymer chain end control mechanism for stereocontrol Figure 8-13 shows this model for syndiotactic placement with secondary insertion (The original reference [Boor and Youngman, 1966] for this gure incorrectly showed propagation proceeding by primary insertion; see Sec 8-4c) The polymer chain end control model for syndiotactic placement is similar to the catalyst site control model for isotactic placement in the both are based on an octahedral transition metal complex that has an alkyl ligand as the propagating site and a coordination vacancy for complexing monomer (A mechanism based.

Fig. 8-13 Polymer chain end control model for syndioselective polymerization. After Boor and Youngman [1966] (by permission of Wiley-Interscience, New York).

on pentacoordinated vanadium instead of hexacoordinated vanadium has also been proposed [Zambelli and Allegra, 1980]). There are important differences between the catalyst site and polymer chain end control models. The homogeneous syndioselective initiator allows coordination of the monomer (and insertion into the polymer chain) via either of the monomer faces. The initiator achieves its stereoselectivity in essentially the same manner as lowered temperature in a noncoordination polymerization. Hindrance between the methyl group of the last unit of the propagating chain and the ligand(s) attached to vanadium prevent rotation about the transition metal carbon bond. This brings into play the repulsive interaction between methyl groups of the terminal monomer unit and incoming monomer. Syndiotactic placement is energetically favored as methyl methyl interactions force the monomer to be coordinated at its opposite face at each successive propagation step. On the other hand, monomer monomer interactions are minimized with isoselective initiators by rotation about the transition metal carbon bond.

. . ....

Isotactic placement occurs since only one con guration is favored for coordination and addition of monomer to the propagating chain Isotactic placement proceeds with migration of the polymer chain to its original ligand position prior to the next propagation step Syndiotactic propagation occurs alternately at the two ligand positions In summary, syndioselective initiators exaggerate the inherent tendency toward syndiotactic placement by accentuating the methyl methyl repulsive interactions between the propagating chain end and incoming monomer Isotactic placement occurs against this inherent tendency when chiral active sites force monomer to coordinate with the same enantioface at each propagation step The polymer chain end control model is supported by the observation that highly syndiotactic polypropene is obtained only at low temperatures (about 78 C) Syndiotacticity is signi cantly decreased by raising the temperature to 40 C [Boor, 1979] The polymer is atactic when polymerization is carried out above 0 C.

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