Oxygen insertion of o-quinone under catalytic hydrogenation conditions

Org Lett. 2013 Mar 15;15(6):1162-5. doi: 10.1021/ol400164e. Epub 2013 Mar 1.

Abstract

An oxygen-insertion reaction that transforms an o-quinone and a conjugated α-diketone substrate into an anhydride product or derivative under catalytic hydrogenation conditions is reported. The experiments and computations indicate that the oxygen insertion proceeds via a radical mechanism mediated by an acetoxyl radical.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclic N-Oxides / chemistry
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Hydrogenation
  • Molecular Structure
  • Oxygen / chemistry*
  • Picrates / chemistry
  • Quinones / chemistry*

Substances

  • Biphenyl Compounds
  • Cyclic N-Oxides
  • Heterocyclic Compounds
  • Picrates
  • Quinones
  • 1,1-diphenyl-2-picrylhydrazyl
  • Oxygen
  • TEMPO