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et al., 1966; Pasquon et al., 1989]. Two possible routes are possible, ring-opening metathesis polymerization (ROMP) (Sec. 7-8) and polymerization through the double bond, for example, for cyclobutene.
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CH2 CH2 XLII CH CH CH2 CH2 CH2 CH
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XLIII
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Four different stereoisomers are possible for polymer XLII, poly(cyclobutane-1,2-diyl) (Sec. 8-1f). Cis and trans isomers are possible for polymer XLIII, poly(but-1-ene1,4-diyl). (XLIII is the same polymer obtained by the 1,4-polymerization of 1,3-butadiene Sec. 8.10). Traditional Ziegler Natta initiators based on vanadium and metallocene initiators yield polymerizations almost exclusively through the double bond. Titanium, tungsten, and ruthenium initiators yield predominantly ROMP with varying amounts of cis and trans placements. Cyclopentene yields mixtures of ROMP and double-bond polymerization with some Ti and V initiators. ROMP occurs exclusively with molybdenum and tungsten initiators, as well as Re, Nb, and Ta initiators. The relative amounts of cis and trans structures vary with the initiator and temperature [Dall Asta et al., 1962; Pampus and Lehnert, 1974]. Metallocene initiators polymerize cyclopentene through the double bond, but the polymer structure consists of cis 1,3-placement (Coates, 2000; Kaminsky, 2001; Kelly et al., 1997]. 1,3-Placement occurs through an isomerization process similar to that responsible for 3,1placement in propene polymerization (Sec. 8-5c-1). 1,3-Placement is also observed with nickel and palladium a-diimine initiators [Sacchi et al., 2001] (Sec. 8-8b). 1,3-Placement has not been reported for other cycloalkene polymerizations. Cyclohexene does not polymerize by either route except when it is part of a bicyclic structure as in norbornene. Stereochemistry in the ROMP of norbornene is complicated since the polymer, LXVI in Sec. 7-8, has possibilities of isomerism at both the ring and the double bond. Most polymerizations by the typical ROMP initiators yield cis stereochemistry at the cyclopentane ring with varying amounts of cis and trans placements at the double bond [Ivin, 1987]. Metallocene initiators yield predominantly double-bond polymerization with 1,2-placement [Janiak and Lassahn, 2001]. Little is known about the R/S isomerism (i.e., erythro and threo ditactic structures are possible) at the stereocenters that result from double-bond polymerization. Cycloheptene and higher cycloalkenes undergo only ROMP; double-bond polymerization does not occur because the larger rings can accommodate the double bond without being highly strained.
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Styrene
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Styrene is slightly polar compared to ethylene and a-ole ns. The lack of a strongly polar functional group allows styrene to undergo highly (>95 98% ) isoselective polymerization
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STEREOCHEMISTRY OF POLYMERIZATION
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with many of the heterogeneous traditional Ziegler Natta initiators effective for a-ole ns [Longo et al., 1990; Pasquon et al., 1989; Soga et al., 1988]. Highly (>95 98%) syndiotactic polystyrene is obtained using a variety of soluble titanium initiators such as CpTiCl3 and Cp2 TiCl2 , and various substituted cyclopentadienyl analogs with MAO [Coates, 2000; Ishihara et al., 1988; Minieri et al., 2001a,b; Pellecchia et al., 1987; Po and Cardi, 1996; Schellenberg and Tomotsu, 2002; Schwecke and Kaminsky, 2001; Zambelli et al., 1989]. Zirconium initiators are also useful, but their activity is lower than that of the titanium initiators. Partially isotactic polystyrenes are obtained with n-butyllithium in toluene at 40 C and the heterogeneous al n initiator (allylsodium sodium isopropoxide NaCl) in hexane at 20 C [Braun et al., 1960; Kern, 1960]. Partially syndiotactic polystyrenes are obtained with many different initiators, including n-butyllithium in toluene at 25 C and higher temperatures and cesium naphthalene in toluene at 0 C or THF at 78 C [Kawamura et al., 1982]. There is little tendency toward stereoselectivity with cationic initiators, although polymerizations of a-methylstyrene by BF3, SnCl4 , and other Lewis acids give moderate syndioselectivity [Wicke and Elgert, 1977].
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Alkynes
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Acetylene is polymerized to polyacetylene [IUPAC: poly(ethene-1,2-diyl)] by Ziegler Natta initiators such as titanium tetraisobutoxide with triethylaluminum [Ito et al., 1974; Shelburne and Baker, 1987; Shirakawa, 2001; Theophilou and Naarman, 1989]. Polymerization at
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