Abstract
Vinyl polymers containing about 20 mol-% of trimethylsilyl or tertbutyldimethylsilyl enol ether functionalities were synthesized by copolymerizing styrene or methyl methacrylate with either 2-trimethylsiloxybutadiene or 2-(tertbutyldimethysiloxy)butadiene under classical free-radical polymerization conditions. The reactivity of the resulting polymers toward a set of classical electrophilic reagents was investigated. Selected electrophiles included water, p-toluenesulfonyl isocyanate ([2+2]-cycloaddition), aromatic and aliphatic aldehydes (aldol reaction), benzaldehyde dimethyl acetal (Noyori condensation), and bromine. Detailed analysis of the polymer final structure - including quantitative 1H- and 13C-NMR analysis - demonstrated that in most cases the silyl enol ether group displays the same reactivity pattern as low-molecular weight analogs.
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