Chemistry of acetylenic ethers: 78 Isomerization of some conjugated enyne compounds

Enyne-hydrocarbons, -alcohols and -ethers with the system can be converted into the isomers with a terminal acetylenic group , by treating them with an excess of potassium amide in liquid ammonia and hydrolysing the reaction mixture thus formed. In most cases yields are excellent. Enyne thioethers RCC-CHCH-SC2H5 (R alkyl) undergo an elimination of ethanethiol under these conditions. Hydrolysis affords the 1,3-diynes RCC-CCH in very good yields.