Synthesis of 1-oxa-2-silacyclopentane derivatives via intramolecular nucleophilic attack at silicon

Metalation of (HSiMe2)3CH with lithium diisopropylamide (LDA) in THF gives (HSiMe2)3CLi, which reacts with ethylene oxide, propylene oxide, 1,2-epoxy butane, 1,2-epoxy pentane, 1,2-epoxy hexane, and epichlorohydrin to give the corresponding 1-oxa-2-silacyclopentane derivatives. Then, glycidylmethacrylate (GM) random copolymers with styrene (St) (in a 1:1 and 1:3 mol ratio) were synthesized by solution free radical polymerization at 70(±1) °C using α,α′-azobis(isobutyronitrile) (AIBN) as an initiator. Both types of copolymers were treated with (HSiMe2)3CLi to give new modified copolymers. The reaction of (HSiMe2)3CLi with epoxides on the side chains of the copolymers does not lead to intramolecular nucleophilic attack contrary to simple epoxides. All the products have been characterized by spectroscopic techniques.