Chemistry of 1,3-diarylpropynones in superacids

Org Biomol Chem. 2004 Dec 7;2(23):3483-9. doi: 10.1039/b412323a. Epub 2004 Nov 2.

Abstract

In superacids with H0=-14 to -20, it has been found that 1,3-diarylpropynones ArC triple bond CCOAr' are either protonated on oxygen of carbonyl groups with the formation of stable ions ArC triple bond CC(O+H)Ar' or undergo further transformations when the highly conjugated system is electron-rich enough. In the latter case, 3-arylindenones are produced very rapidly and with high efficiency (up to 95% yield in less than 30 min). The influence of the substituents Ar, Ar' and of the reaction conditions on the behavior of 1,3-diarylpropynones and on the intramolecular cyclisation have been studied. From the collected data, a mechanism has been proposed involving vinyl cations ArC+=CHCOAr' and/or dications ArC+=CHC(O+H)Ar'.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Homosteroids / chemical synthesis
  • Homosteroids / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Propane / chemistry*

Substances

  • Acids
  • Homosteroids
  • Propane