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Keywords:

  • Phosphorus;
  • Vinyl phosphonate;
  • Ene diamine;
  • Multinuclear NMR spectroscopy;
  • X-ray diffraction

Abstract

First examples of ene diamines with a phosphonate function at the C=C double bond were obtained by the reaction of dialkyl H-phosphonates with bis(N-tert-butyl)-diimine derived from glyoxal, [1,4-bis(tert-butyl)-1,4-diaza-1,3-butadiene], and isolated as hydrochlorides. Preferentially the cis-diamine is formed. The new phosphonates are characterized by multinuclear NMR spectroscopy(1H, 13C, 31P). In addition the methyl ester 8a was characterized by 14,15N NMR spectroscopy as well as by several 2D NMR techniques and single-crystal X-ray diffraction, unequivocally establishing the ene diamine structure. In the crystal dimers of the cations are formed by P–O···H–N hydrogen bonding.