Formic Acid Reduction. VII. Reduction of Carbon-Carbon Double Bonds adjacent to Carbonyls

Triethylammonium formate, TEAF given by 5HCOOH·2N (C2H5)3 has been introduced as a reagent effective for reduction of carbon-carbon double bond adjacent to carbonyl group, preferably double bond of central methylene carbon of 1, 3-diketone. The reduction is selective at the carbon-carbon double bond. Nitro group, carbonyl group and other carbon-carbon double bond such as cinnamyl of substrate are not affected by the reduction. An improvement in the preparation of substrate compounds, α, β-unsaturated ketones, using boron trioxide as a dehydrating agent, is also given.