Reactions of elemental phosphorus and phosphines with electrophiles in superbasic systems: XIII. Phosphorylation of phenylacetylene with active modifications of elemental phosphorus

Phosphorylation of phenylacetylene with white or activated red phosphorus ( prepared from white phosphorus under the action of ionizing radiation) occu rs in KOH-DMSO or KOH-HMPA systems with heat evolution and stereoselective formation of Z isomers of tristyrylphosphine and -phosphine oxide in yields of 48-49% and 10-15%, respectively. Under the comparable conditions the co mmercial red phosphorus is considerably less reactive toward phenyl acetyle ne: The total yield of the above-mentioned products is 5%.