CH2 CH CH2CH(CH3)2 H CH2 in .NET

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CH2 CH CH2CH(CH3)2 H CH2
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C+ CH2CH(CH3)2 XI H
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CH3 H CH2CH2CH C + CH3 XV
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The driving force in some isomerization polymerizations is relief of steric strain. Polymerization of b-pinene proceeds by the rst-formed carbocation XVI rearranging to XVII
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IONIC CHAIN POLYMERIZATION
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via cleavage of the strained four-membered ring and migration of the resulting gem-dimethyl carbocation center [Kennedy and Marechal, 1982].
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CH3 CH2 C+ CH3 XVII
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Other monomers that undergo isomerization polymerization include 5-methyl-1-hexene, 4,4-dimethyl-1-pentene, 6-methyl-1-heptene, a-pinene, and vinylcyclopropane [Cesca, 1985; Corno et al., 1979]. 5-2c Chain Transfer and Termination
Various reactions lead to termination of chain growth in cationic polymerization [Allen and Bevington, 1990; Dunn, 1979; Gandini and Cheradame, 1985; Kennedy and Marechal, 1982; Matyjaszewski and Pugh, 1996]. Many of the reactions that terminate the growth of a propagating chain do not, however, terminate the kinetic chain because a new propagating species is generated in the process. 5-2c-1 b-Proton Transfer
Transfer of a b-proton from the propagating carbocation is the most important chain-breaking reaction. It occurs readily because much of the positive charge of the cationic propagating center resides not on carbon, but on the b-hydrogens because of hyperconjugation. Monomer, counterion or any other basic species in the reaction mixture can abstract a b-proton. Chain transfer to monomer involves transfer of a b-proton to monomer with the formation of terminal unsaturation in the polymer.
H CH2C(CH3)2
n CH2C(CH3)2(BF3OH)
+ CH2
C(CH3)2 CH2
5-17a
(CH3)3C +(BF3OH) + H CH2C(CH3)2 + H CH2C(CH3)2
n CH
n CH2C(CH3)
C(CH3)2
HMnM +(IZ) + M
ktr, M
Mn + 1 + HM +(IZ)
5-17b
There are two different types of b-protons, and two different unsaturated end groups are possible for isobutylene as well as some other monomers such as indene and a-methylstyrene. The relative amounts of the two end groups depend on the counterion, identity of the propagating center, and other reaction conditions. Only one type of unsaturated end group (internal) is possible for other monomers such as styrene, ethyl vinyl ether, and coumarone. It should be noted that the kinetic chain is not terminated by this reaction since a new propagating species is regenerated. Many polymer molecules are usually produced for each initiator coinitiator species present. Chain transfer to monomer is on much more
CATIONIC POLYMERIZATION OF THE CARBON CARBON DOUBLE BOND
favorable terms with propagation in many cationic polymerizations compared to radical polymerization. Since it is kinetically indistinguishable from propagation, the relative rates of transfer and propagation are given by the ratio ktr;M =kp , which is the chain-transfer constant for monomer CM. The value of CM determines the molecular weight of the polymer if other chain-breaking processes are not signi cant. The larger the value of CM the lower will be the molecular weight. Chain transfer to monomer is the principal reaction that limits polymer molecular weight for most monomers, especially at reaction temperatures higher than about 20 C. Since chain transfer to monomer generally has a higher activation energy than propagation, it is usually suppressed by working at lower reaction temperatures. Another type of chain transfer to monomer reaction is that involving hydride ion transfer from monomer to the propagating center [Kennedy and Squires, 1967].
H CH2C(CH3)2 CH2 C(CH3)
n CH2C(CH3)2(BF3OH)
+ CH2
C(CH3)2
n CH2CH(CH3)2
CH2(BF3OH)
+ H CH2C(CH3)2
5-18
This reaction may account in part for the oligomers obtained in the polymerization of propene, 1-butene, and other 1-alkenes where the propagation reaction is not highly favorable (due to the low stability of the propagating carbocation). Unreactive 1-alkenes and 2-alkenes have been used to control polymer molecular weight in cationic polymerization of reactive monomers, presumably by hydride transfer to the unreactive monomer. The importance of hydride ion transfer from monomer is not established for the more reactive monomers. For example, hydride transfer by monomer is less likely a mode of chain termination compared to proton transfer to monomer for isobutylene polymerization since the tertiary carbocation formed by proton transfer is more stable than the allyl carbocation formed by hydride transfer. Similar considerations apply to the polymerizations of other reactive monomers. Hydride transfer is not a possibility for those monomers without easily transferable hydrogens, such as N-vinylcarbazole, styrene, vinyl ethers, and coumarone. The two types of chain transfer to monomer are kinetically indistinguishable, but one (Eq. 5-17) results in unsaturated end groups, while the other (Eq. 5-18) results in saturated end groups. Chain transfer to counterion, also called spontaneous termination, involves transfer of a b-proton to the counterion. The initiator coinitiator is regenerated by its expulsion from the propagating species and, as in chain transfer to monomer, the polymer molecule has a terminal double bond
H CH2C(CH3)2
n CH2C(CH3)2(BF3OH)
BF3 OH2 + H CH2C(CH3)2
n CH2C(CH3)