Abstract

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 cyclopropycarbinyl 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 functionalised cyclohexane derivatives. A general mechanism is proposed.

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