The structure of a by-product obtained during the reduction of 2-phenyl-1-cyanoacrylic acid

Abstract

The by-product, C₂₃H₁₈N₂O, obtained during the reduction of 2-phenyl-1-cyanoacrylic acid by sodium amalgam, has been shown by X-ray analysis to be 5-cyano-1,4,5-triphenylpyrrolidin-2-one with the two C-phenyl groups trans to each other. Its formation is attributed to the presence of 2-phenylaminobenzyl cyanide in the 2-phenyl-1-cyanoacrylic acid and a rational synthesis of it is described, together with details of the structure analysis.