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2-[Anilino(diphenylphosphoryl)methyl]phenol from a three-component Kabachnik-Fields reaction.

Ming-Shu WuQing-Qin FengGao-Nan LiDe-Hui Wan
Published in: Acta crystallographica. Section C, Crystal structure communications (2013)
The title compound, C25H22NO2P, was synthesized in high yield by a three-component Kabachnik-Fields reaction of diphenylphosphine oxide, salicylaldehyde and aniline in dry toluene at room temperature. It precipitates as racemic crystals, in which strong hydrogen bonds between the hydroxy group and the P=O group of a neighbouring molecule form one-dimensional heterochiral chains along the crystallographic a axis, with an O···O separation of 2.568 (2) Å. The pseudo-tetrahedral environment of the P atom is distorted, with O-P-C bond angles significantly larger than the C-P-C angles.
Keyphrases
  • room temperature
  • electron transfer
  • ionic liquid
  • molecular dynamics