Synthesis of novel functional styrene monomers having trimethylsilyl and hydroxyalkyl groups by the reaction between 4‐vinylbenzyllithium derivatives and oxiranes

摘要: New synthetic routes for styrene derivatives having both trimethylsilyl and hydroxyalkyl groups were investigated. Reactions between oxirane (5a) chemical species present in an equilibrium system resulting from 4-(trimethylsilylmethyl)styrene (1s) lithium diisopropylamide (2) tetrahydrofuran give addition product (8a) 2 5a preferentially. By using alkyl-substituted oxiranes such as ethyloxirane (5c) tert-butyloxirane (5e), a 1 : reaction of 1s with the takes place predominantly to form 1-alkyl-3-trimethylsilyl-3-p-vinyl-phenyl-1-propanol (8) homologues. From results studies on several oxiranes, it was concluded that selective formation 8 homologues attained by suppression reactions owing steric hindrance alkyl substituents isopropyl 2. The reactivity polymerization also estimated basis spectroscopic measurements. found have similar (1s).