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

✍ Scribed by Kazem D. Safa; Mohammad Shahrivar; Shahin Tofangdarzadeh; Akbar Hassanpour

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
788 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Tris(dimethylsilyl)methyl lithium, (HSiMe~2~)~3~CLi, reacts with allyl, phenyl, benzyl, n‐propyl and n‐butyl glycidyl ethers in THF at ‐5 °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) °C with α,α‐azobis(isobutyronitrile) (AIBN) as initiator, contained pendant epoxide functions. Treatment of these with (HSiMe~2~)~3~CLi did not lead to intramolecular nucleophilic attack as found for simple epoxides.

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