Organic Chemistry in water (part II). NUCLEOPHILIC ADDITION OF WATER-SOLUBLE PHOSPHINES ON ACTIVATED OLEFINS

Article abstract of DOI:10.1016/S0040-4020(01)89800-8

Triphenylphosphine m-trisulfonate P(PhSO3Na)3 = TPPTS and triphenylphosphine m-monosulfonate Ph2PPhSO3Na = TPPMS react in water with α,β unsaturated acids affording hydrosoluble phosphonium salts.The conversion is quantitative because water readily protonates the carbanionic intermediate thus displacing the equilibrum towards the right.This nucleophilic addition of hydrosoluble phosphines has been extended to non water miscible activated olefins in biphasic media; depending on the pH, phosphine oxides or phosphonium salts are obtained.When the reactions are carried out in D2O, the addition products are specifically deuterated.