NOVEL SYNTHESIS OF ALPHA-METHYLENE CARBONYL-COMPOUNDS

The reaction of enol acetates or silyl enol ethers with α-chloromethyl methyl ether in the presence of active zinc compounds followed by an acid-catalyzed elimination of methanol from the resulting α-methoxymethyl ketones led to regioselective synthesis of α-methylene ketones in satisfactory overall yields. Furthermore, this novel reaction was applicable to the introduction of a methylene group to the y position of a,β-unsaturated ketones and the a position of carboxylic esters including γ-butyrolactone. © 1979, American Chemical Society. All rights reserved.