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It has been reported by Cainelli that the reaction of benzaldehyde with methylene iodide and the amalgam of magnesium with mercury affords styrene. When a small amount of mercury was used for this reaction, the yield of styrene was remarkably increased (Fig.1). According to this method, following aldehydes and ketones gave the corresponding carbonyl-methylenated products in the yields given in the parentheses: p-methylbenzaldehyde (75 %), p-chlorobenzaldehyde (67 %), n-heptaldehyde (48 %), diethyl ketone (68 %), cyclohexanone (38 %).

An Improvement for the Synthesis of Terminal Olefin from Carbonyl Compounds by Methylene Iodide and Magnesium Amalgam