HYDRATION REACTIONS OF PHOSPHORYLATED 1,3-ENYNES

Abstract

Hydration of the 3-alkene-1 -ynephosphonic dimethyl esters 3 in the presence of a mixture of mercuric sulfate and sulfuric acid as a catalyst takes place with addition of water to the triple bond and hydrolysis of the phosphonate group with formation of the 2-oxo-3-alkenephosphonic acids 4. Ketalation of the 3-alkene-1-ynephosphonic dimethyl esters 3 with methanol using as a catalyst a mixture of yellow mercuric oxide, trichloroacetic acid and boron trifluoride etherate and subsequent hydrolysis of the prepared phosphorylated ketals B leads to the 2-oxo-3-alkenephosphonic dimethyl esters 5. Treatment of 3 with water in the presence of concentrated hydrochloric acid yields the 3-alkene-1-ynephosphonic acids 6.

Key Words:

• 3-alkene-1-ynephosphonic dimethyl esters
• mercuric catalysts
• hydration
• hydrolysis
• 2-oxo-3-alkenephosphonic acids
• ketalation
• 2-oxo-3-alkenephosphonic dimethyl esters: 3-alkene-1-ynephosphonic acids