Reaction of Carbonyl Compounds with Organomagnesium Reagent Formed from Methylene Iodide and Magnesium

Abstract

Products from the reactions between carbonyl compounds and organomagnesium reagent obtained from methylene iodide and magnesium turnings were investigated. When benzaldehyde (50 mmol) was allowed to react with methylene iodide (50 mmol) and magnesium turnings (103 mmol) in ether for 2 hours under gentle reflux, styrene (29%), benzyl alcohol (22%), and 1-phenylethyl alcohol (5%) were obtained, accompanying the formation of considerable amount of tarry residue after distillation (Table 1). Other aldehydes and ketones also gave carbonylmethyle nated products [1], reduction products (alcohols) [2], and reductively methylated products [3] (Table 2). The formation of alcohols ([2] and [3]) and tarry matter appaers to limit the yield of the carbonyl-methylenated product [1].