Hexachloroacetone as a precursor for a tetrachloro-substituted oxyallyl intermediate: [4+3] cycloaddition to cyclic 1,3-dienes

Molecules. 2004 Jan 31;9(1):1-10. doi: 10.3390/90100001.

Abstract

The enol phosphate 2,2-dichloro-1-(trichloromethyl)ethenyl diethyl phosphate (1), easily available by a Perkow reaction between hexachloroacetone and triethyl phosphite, reacts with sodium trifluoroethoxide/trifluoroethanol in the presence of cyclic 5-membered 1,3-dienes to furnish alpha,alpha,alpha',alpha'-tetrachloro-substituted[3.2.1]bicyclic ketones 2. A [4+3] cycloaddition of a tetrachloro-oxyallyl intermediate is postulated.

MeSH terms

  • Acetone / analogs & derivatives*
  • Acetone / chemistry
  • Allyl Compounds / chemistry*
  • Cyclization
  • Hydrocarbons, Cyclic / chemistry*
  • Ketones / chemistry
  • Molecular Structure

Substances

  • Allyl Compounds
  • Hydrocarbons, Cyclic
  • Ketones
  • Acetone
  • hexachloroacetone