10.1021/ja01874a043
The study investigates the relative reactivities of methylmagnesium chloride and dimethylmagnesium, focusing on their interactions with various carbonyl compounds in different solvents. Methylmagnesium chloride and dimethylmagnesium are the primary reagents used, with dioxane and isoamyl ether serving as solvents. The researchers found that dimethylmagnesium exhibits a preference for reacting with hydroxyl groups over carbonyl groups, forming ene-diol magnesium salts and resulting in less reactivity toward carbonyl functions compared to methylmagnesium chloride. This was demonstrated through reactions with benzoin, acetophenone, desoxybenzoin, and diphenylacetophenone, where dimethylmagnesium showed lower yields and incomplete reactions. The study also highlights the influence of solvents on reaction outcomes and suggests that the presence of dioxane does not alter the reaction course significantly.