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New straightforward route for the synthesis of some 1‐oxa‐2‐silacyclopentane derivatives
Author(s) -
Safa Kazem D.,
Shahrivar Mohammad,
Tofangdarzadeh Shahin,
Hassanpour Akbar
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450215
Subject(s) - chemistry , epoxide , glycidyl methacrylate , intramolecular force , styrene , polymer chemistry , nucleophile , polymerization , copolymer , double bond , ring (chemistry) , methyl methacrylate , lithium (medication) , medicinal chemistry , organic chemistry , catalysis , polymer , medicine , endocrinology
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 SiH bond into an SiO 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.