Solvent Effects in the Grignard Reaction. Ethylmagnesium Bromide with Benzonitrile

Organometallic reaction mechanisms. IV. Mechanism of ketone reduction by aluminum alkyls

“…Also previous studies concerning the effect of solvent in the nucleophilic addition of ethylmagnesium bromide with benzonitrile indicated that the reaction rate also decreases as the basicity of the solvent increases. 20 The explanation offered for this effect was that the formation of the product proceeds through complex formation. Since the complex is formed by displacement of one of the solvent molecules coordinated to the Grignard compound (eq 7 and 8), the more basic solvent would result in more -difficult displacement of the solvent and hence a smaller concentration of complex (smaller K).…”