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

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