One-Pot Synthesis of Stable Phosphorus Ylides Using CH-Acid Compounds

Stable crystalline phosphorus ylides were obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine and di-tert-butyl acetylendicarboxylate, in the presence of antron, dimedone, indandion, and 3,5-dimethylbarbituric acid. These stable ylides exist in a solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group.

Keywords:

• Acetylenic ester
• CH-acids
• geometrical isomers
• stable phosphorus ylides
• triphenylphosphine