Reactivity of electrophilic reagents towards silyl enol ether groups incorporated into vinyl polymers
(1997) Tetrahedron — Vol. 53, n° 45, p. 15429-15444 (1997)
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- 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 H-1- and C-13-NMR analysis - demonstrated that in most cases the silyl enol ether group displays the same reactivity pattern as low-molecular weight analogs. (C) 1997 Elsevier Science Ltd.
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Penelle, J., & Mayne, V. (1997). Reactivity of electrophilic reagents towards silyl enol ether groups incorporated into vinyl polymers. Tetrahedron, 53(45), 15429-15444. https://doi.org/10.1016/S0040-4020(97)00971-X (Original work published 1997)