New straightforward route for the synthesis of some 1-oxa-2-silacyclopentane derivatives

摘要

Tris(dimethylsilyl)methyl lithium, (HSiMe2)(3)CLi, reacts with allyl, phenyl, benzyl, n-propyl and n-butyl glycidyl ethers in THF at -5 degrees C to give 1-oxa-2-silacyclopentane derivatives. It seems that ring closure is facilitated by conversion of the Si-H bond into an Si-O bond. Glycidyl methacrylate (GM) random copolymers with 4-methyl- and 4-methoxy styrene, synthesized by solution free radical polymerization at 70 (+/- 1) degrees C with alpha,alpha-azobis(isobutyronitrile) (AIBN) as initiator, contained pendant epoxide functions. Treatment of these with (HSiMe2)(3)CLi did not lead to intramolecular nucleophilic attack as found for simple epoxides.