Cleavage of oximes using a solid supported hypervalent organoiodine reagent

Comb Chem High Throughput Screen. 2005 Aug;8(5):445-7. doi: 10.2174/1386207054546522.

Abstract

A facile and efficient oxidative cleavage of oximes to form carbonyl compounds is reported using phenyl iodonium (III) diacetate (PIDA) and polymer supported polydiacetoxyiodostyrene. Regeneration of carbonyl compounds from corresponding oximes is an important reaction, since oxime derivatives constitute one of the primary methods for purification and characterization of carbonyl compounds. This process overcomes many of the disadvantages associated with other oxidative methods such as long reaction times, difficulties in isolation of products and formation of over oxidized products.

MeSH terms

  • Acetates / chemistry
  • Indicators and Reagents
  • Iodine / chemistry*
  • Models, Chemical
  • Organic Chemicals / chemistry*
  • Oxidation-Reduction
  • Oximes / metabolism*
  • Polystyrenes / chemistry

Substances

  • Acetates
  • Indicators and Reagents
  • Organic Chemicals
  • Oximes
  • Polystyrenes
  • Iodine