Synthesis and structural investigation of N-acyl selenophosphoramides

Org Biomol Chem. 2009 Oct 7;7(19):4095-100. doi: 10.1039/b907641g. Epub 2009 Aug 7.

Abstract

2-Amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinane reacts with acyl chlorides (4-chlorobenzoyl chloride or pivaloyl chloride) yielding the respective N-acyl selenophosphoramides. These derivatives do not isomerise to the related selenocarbonyl imides. X-ray study of N-(4-chlorobenzoyl)-2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinane indicates that the selenium atom is placed in the equatorial position. The next compound studied, N-pivaloyl-2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinane, crystallises with both axial/equatorial conformers present in the asymmetric unit. Finally, 2-amino-2-seleno-5,5-dimethyl-1,3,2-dioxaphosphorinane is present in the solid state in the form with the selenium atom in the axial position. The results are presented together with X-ray structures of previously synthesised and described cyclic O-acyl monoselenophosphates.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry*
  • Crystallography, X-Ray
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Phosphoramides
  • Phosphoric Acids / chemical synthesis*
  • Phosphoric Acids / chemistry*
  • Quantum Theory
  • Selenium / chemistry*

Substances

  • Amides
  • Phosphoramides
  • Phosphoric Acids
  • phosphoramide
  • Selenium