Starting from allylmethylphenylaminosilanes, (E)-alkenyl(methyl)phenylsilanols were synthesized through alkylation of allyl(amino)silane carbanions with halides, followed by hydrolysis of alkenyl(amino)silane, which was produced in the alkylation, under very mild condition. Regioselectivity of the alkylation was studied, and the method for removing a-isomer out from the mixture of the product was developed. E.g., aminosilane I was lithiated, alkylated with n-pentyl iodide to give, after refluxing with NaI and Me3SiCl in EtOH, 83% II (R = n-pentyl, R1 = Et)(III). Hydrolysis of III gave 72% silanol II (R = n-pentyl, R1 = H).

Key words: ALKYLATION, SELECTIVITY, SILANE, SILANOL, ALLYL GROUP