Total Synthesis and Characterization of 7-Hypoquinuclidonium Tetrafluoroborate and 7-Hypoquinuclidone BF3 Complex

J Am Chem Soc. 2016 Jan 27;138(3):969-74. doi: 10.1021/jacs.5b11750. Epub 2016 Jan 12.

Abstract

Derivatives of the fully twisted bicyclic amide 7-hypoquinuclidone are synthesized using a Schmidt-Aubé reaction. Their structures were unambiguously confirmed by X-ray diffraction analysis and extensive spectroscopic characterization. Furthermore, the stability and chemical reactivity of these anti-Bredt amides are investigated. 7-Hypoquinuclidonium tetrafluoroborate is shown to decompose to a unique nitrogen bound amide-BF3 complex of 7-hypoquinuclidone under anhydrous conditions and to react instantaneously with water making it one of the most reactive amides known to date.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boranes / chemical synthesis*
  • Boranes / chemistry
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Quinuclidines / chemical synthesis*
  • Quinuclidines / chemistry

Substances

  • 7-hypoquinuclidone
  • 7-hypoquinuclidonium tetrafluoroborate
  • Boranes
  • Quinuclidines
  • boron trifluoride