Formation and Reactions of Diorganophosphinite Ions in Liquid Ammonia. Synthesis of Triorganophosphine Oxides by the SRN1 Mechanism

Article abstract of DOI:10.1021/jo00295a019

The reaction of triphenyl- and tribenzylphosphine oxides with alkali metals in liquid ammonia gave diphenyl- and dibenzylphosphinite ions, respectively, in high yields and a small amount of deoxygenated products.These ions reacted under photostimulation with aryl halides by the S_RN1 mechanism to give aryldiphenyl- and aryldibenzylphosphine oxides in good yields.With tribenzylphosphine oxide, by consecutive debenzylation with alkali metals followed by photostimulated reaction with aryl halides, all the benzylic moieties could be replaced by aromatic moieties to finally obtain unsymmetrical triarylphosphine oxides.