A Comparison of Phosphonium and Phosphonate Carbanion Reagents inReactions with 1,3-Diphenyl-2-(hydroxyimino)-1,3-propanedione

Abstract 1,3-Diphenyl-2-(hydroxyimino)-1,3-propanedione 1 reacted with phosphonium ylides 2A,B to give mainly the substituted 1-hydroxy-2,3-dihydropyrroles 6A,B along with the novel ylides 10A,B whereas the phosphono substituted-N-heterocycles 11A,B and 14A,B were obtained from the reaction of 1 with α-phosphoryl carb­anion counterparts 3A,B. Reaction of 1 with cyanomethylene(tri­phenyl)phosphorane 2C afforded the Wittig product 17 and the oxazole derivative 18 while the phosphono 2,2-disubstituted dihydrooxazole 20 and the diolefin 19 were produced in the reaction with the phosphonate ylide 3C. Application of the unsaturated carb­anions 2D and 3D on 1 yielded the pyrrole 23 and the phosphono substituted 2H-1,4-oxazine 25, respectively.