Over the past decade, a few novel silylenoids have been the subject of the extensive study. Silylenoid (R2SiMX) is a species which has an electropositive metal (M, alkali metal) and a leaving group (X, usually halogen) bound to the same silicon atom. Recently, we reported halosilylenoids, which were stable at room temperature. Bromosilylenoid 1, having the bulky substituent, Tsi (= trisyl, tris(trimethylsilyl)methyl group), was synthesized by the reduction of tribromotrisylsilane with 2 equivalent of LiNp (lithium naphtalenide). Using the bromosilylenoid, 1, we studied its reactivity with various carbonyl compounds, such as dimethylpentanone, adamantanone, cyclohexanone and dimethylcyclohexanone.
In the reaction of 1 with cyclohexanone, after an excess amount of cyclohexanone were added to bromosilylenoid, 1, the treatment of the reaction mixture with an excess of H2O, MeOH, i-PrOH and t-BuOH gave the corresponding products. In this presentation, we will discuss the chemistry of bromosilylenoid with ketones.