ORGANIC CHEMISTRY IN WATER (PART V) NUCLEOPHILIC ADDITION OF WATER-SOLUBLE PHOSPHINES ON ACTIVATED ALKYNES: AN EFFICIENT SYNTHESIS OF NEW VINYLPHOSPHONIUM SALTS AND OF SPECIFICALLY DEUTERATED OLEFINS.

Article abstract of DOI:10.1016/S0040-4020(01)96009-0

Triphenylphosphine m-trisulfonate 1 and triphenylphosphine m-monosulfonate 2 react in water with activated alkynes R-CC-A (A = CO2H, CO2R1, COR2, CHO) affording new vinylphosphonium salts or vinylphosphine oxides or alkenes depending on the pH of the aqueous solution and on the nature of the substituent R.The reactions of 1 or 2 with alkynes bearing an electron-acceptor substituent R give rise to the corresponding trans disubstituted olefins.Specifically mono or dideuterated alkenes are thus obtained in good yields by sequential use of H2O-D2O.When R = H or Alkyl, vinylphosphonium salts or vinylphosphine oxides are quantitatively produced respectively in acidic or in neutral solution.