Etude de la reactivite de l'allyltrimethylsilane avec les cetones α-cyclopropaniques en presence de tetrachlorure de titane

Article abstract of DOI:10.1016/0022-328X(94)05029-B

The reaction of diversely substituted α-cyclopropylketones with allyltrimethylsilane in the presence of titanium tetrachloride has been studied.The products formation is explained by the intervention of a cyclopropylcarbinyl transient cation formed after a first 1,2-addition on the carbonyl.With regard to the structure of the starting compounds, this intermediate reacts with a second molecule of allylsilane, either by a bimolecular addition on the carbocycle, or by the direct attack on the carbon bearing the formal positive charge yielding diallyl and functionalisedcyclohexane derivatives.A general mechanism is proposed.Keywords: Silicon; Titanium; Allyltrimethylsilane; Lewis acids; Reaction mechanism