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such as (PF6 and (SbCl6 have little tendency to bring about termination by transfer of a halide ion, while counterions of aluminum and tin have appreciable transfer tendencies; others such as (BF4 and (FeCl4 are intermediate in behavior. Termination may also occur by chain transfer with the initiator (e.g., water or alcohol) or a deliberately added chain-transfer agent. Deliberate termination of growth is carried out to produce polymers with speci c molecular weights or, more often, telechelic polymers with speci c end groups. Hydroxyl and amine end groups are obtained by using water and ammonia as chain-transfer agents. Carboxyl-ended telechelics can be obtained by termination with ketene silyl acetal followed by hydrolysis with base [Kobayashi et al., 1989]. The polymerization of 3,3-bis(chloromethyl)oxetane is complicated by the insolubility of the polymer in the reaction mixture. Termination may involve burial of the propagating oxonium ion centers in the solid polymer, resulting in their inaccessibility to further propagation. 7-2b-4 Cyclic Acetals
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Cyclic acetals contain at least one 1,1-dialkoxy grouping [i.e., (RO)2 CH2 or (RO)2 CHR] as part of a cyclic structure. A variety of cyclic acetals undergo facile cationic polymerization [Kubisa, 1996; Penczek and Kubisa, 1977, 1989b; Schulz et al., 1984]. This includes various
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RING-OPENING POLYMERIZATION
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1,3-dioxacycloalkanes such as 1,3-dioxolane (m 2), 1,3-dioxepane (m 4), and 1,3dioxocane (m 5) [Kawakami and Yamashita, 1977a,b; Matyjaszewski et al., 1980; Okada et al., 1978; Plesch, 1976]. The polymers can be considered as copolymers of the O(CH2 m and OCH2 units. 1,3-Dioxane (m 3) does not polymerize as a result of the stability of the 6-membered ring. Other cyclic acetals that have been studied are 1,3,5-trioxane, 1,3,5-trioxepane, 1,3,6,9tetraoxacycloundecane, and 1,3,5,7-tetroxocane (also referred to as 1,3,5,7-tetroxane) [Kawakami and Yamashita, 1979; Munoz-Escalona, 1978; Schulz et al., 1984; Szwarc and Perrin, 1979]. Polymerization of bicyclic acetals has been of interest for synthesizing polysaccharides [Good and Schuerch, 1985; Hirasawa et al., 1988; Okada, 1991; Okada et al., 1989; Sumitomo and Okada, 1984].
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There has been considerable debate on the details of cyclic acetal polymerizations [Penczek, 2000; Plesch, 1976; Szymanski et al., 1983]. First, it was thought that polymerization proceeded exclusively to yield cyclics, but this was not the case. As with all ROPs, reaction conditions can be manipulated to maximize the formation of either polymer or cyclics. (Study of the relative extents of cyclic and polymer has been complicated by the experimental dif culties involved in identifying the presence of cyclics. One needs to bring a variety of experimental tools and skills to bear on the problem, including a combination of size exclusion chromatography and high-pressure liquid chromatography to separate the different components of a reaction mixture followed by high-resolution NMR and mass spectroscopy for chemical identi cation.) Second, there has been controversy over whether the propagating species in cyclic acetal polymerization are oxonium ions (XVIII) as in cyclic ether polymerization or oxycarbocations (also referred to as alkoxycarbocations) (XIX). One assumes the oxycarbocation XIX is more stable than its carbocation counterpart in cyclic ether polymerization since XIX is stabilized via charge dispersal by the adjacent oxygen. However, this
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stabilization is apparently insuf cient to have the oxycarbocation as the propagating species in preference to the oxonium ion. Both experimental and computational data indicate that more than 99.9% of the propagating species are oxonium ions for unsubstituted 1,3-dioxacycloalkanes [Lahti et al., 1990; Penczek, 2000; Szymanski et al., 1983; Xu et al., 1987]. Since oxonium ions are apparently only 100-fold lower in reactivity toward propagation than oxycarbocations, propagation is predominately carried by oxonium ions [Penczek and Kubisa, 1989a,b]. However, propagation by oxycarbocations is signi cant for 2-alkyl-1,3dioxacycloalkanes because of additional stabilization of the positive charge center by the 2-alkyl substituent coupled with steric hindrance toward propagation through oxonium ions.
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