Reaction between triphenylphosphine, dimethy acetylenedicarboxylate and amines produces phosphorus ylids which undergo a smooth reaction with ethyl chlorooxoacetate and triethylamine to produce dimethyl N-aryl-(or alkyl)-4-ethoxy-5-oxo-2,5-dihydro-1 H-pyrole-2,3-dicarboxylates in high yields.
Protonation of the reactive intermediate produced from the reaction between trialkyl phosphites and dimethyl acetylenedicarboxylate by ethyl carbazones of aromatic aldehydes following by conjugate addition of the anion of ethyl carbazone on the phosphonium salt intermediate leads to functionalised phosphonates in good yields. Triphenylphosphine also reacted with dimethyl acetylenedicarboxylate and ethyl carbazones to produce functionalised phosphoranes in good yields.
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