Etude de la reactivite de l'allyltrimethylsilane avec les cetones α-cyclopropaniques en presence de tetrachlorure de titane
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
Monti, Honore,Afshari, Mohammad,Leandri, Gilbert
p. 69 - 78
(2007/10/02)
Reactivite de l'allyltrimethylsilane avec les acetylcyclopropanes en presence d'acide de Lewis
In the presence of Lewis acid, allyltrimethylsilane undergoes 1,2-addition to the carbonyl system of acetylcyclopropanes.A second direct attack of the nucleophilic reagent on the transient cyclopropylcarbynyl cation formed yields diallylic and functionalised cyclohexane derivatives.
Piras, P.,Afshari, M.,Leandri, G.,Monti, H.
p. C9 - C11
(2007/10/02)
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