Selective synthesis of gem-chlorofluorinated nitrogen-containing derivatives after superelectrophilic activation in superacid HF/SbF5

J Org Chem. 2011 Mar 4;76(5):1460-3. doi: 10.1021/jo102225w. Epub 2011 Jan 20.

Abstract

The first direct selective synthesis of novel gem-chlorofluorinated nitrogen-containing building blocks in superacid is reported. The dramatic role of the chlorine atom on the reaction is shown by in situ NMR experiments and allows the involvement of a novel original superelectrophilic activation process in superacid HF/SbF(5) to be postulated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis*
  • Amines / chemistry
  • Antimony / chemistry*
  • Fluorides / chemistry*
  • Hydrofluoric Acid / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amines
  • antimony pentafluoride
  • Antimony
  • Fluorides
  • Hydrofluoric Acid