Oxone-mediated oxidative cleavage of β-keto esters and 1,3-diketones to α-keto esters and 1,2-diketones in aqueous medium

J Org Chem. 2013 Jul 19;78(14):7268-73. doi: 10.1021/jo4009047. Epub 2013 Jul 11.

Abstract

A versatile and highly efficient method for the direct synthesis of α-keto esters and 1,2-diketones has been developed. This approach utilizes the oxidative cleavage of a variety of β-keto esters and 1,3-diketones mediated by an Oxone/aluminum trichloride system. The simple one-step oxidation reaction proceeded selectively in aqueous media to afford products in high yields, short reaction times, and environmentally benign conditions.

Publication types

  • Research Support, Non-U.S. Gov't
  • Retracted Publication

MeSH terms

  • Esters / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Sulfuric Acids / chemistry*
  • Water / chemistry*

Substances

  • Esters
  • Ketones
  • Sulfuric Acids
  • Water
  • potassium peroxymonosulfuric acid