page_title: Fétizon oxidation
section_title: Reactivity
hierarchical_section_title: Fétizon oxidation / Reactivity
context_page_description: Fétizon oxidation is the oxidation of primary and secondary alcohols utilizing the compound silver(I) carbonate absorbed onto the surface of celite also known as Fétizon's reagent first employed by Marcel Fétizon in 1968. It is a mild reagent, suitable for both acid and base sensitive compounds. Its great reactivity with lactols makes the Fétizon oxidation a useful method to obtain lactones from a diol. The reaction is inhibited significantly by polar groups within the reaction system as well as steric hindrance of the α-hydrogen of the alcohol.
context_section_description: Fétizon's reagent is used primarily in the oxidation of primary or secondary alcohols to aldehydes or ketones with a slight selectivity toward secondary alcohols and unsaturated alcohols.  The reaction is typically done in a refluxing dry non-polar organic solvent with copious stirring.  The reaction time varies with the structure of the alcohol and is typically completed within three hours.  A very attractive property of Fétizon's reagent is its ability to be separated from the reaction product by physically filtering it out and washing with benzene.  
  The inability of Fétizon's reagent to oxidize tertiary alcohols makes it extremely useful in the monooxidation of a [1,2] diol in which one of the alcohols is tertiary while avoiding cleavage of the carbon-carbon bond.
  The mildness and structural sensitivity of the reagent also makes this reagent ideal for the monooxidation of a symmetric diol.
  Lactols are extremely sensitive to Fétizon's reagent, being oxidized very quickly to a lactone functionality.  This allows for the selective oxidation of lactols in the presence of other alcohols.  This also allows for a classic use of Fétizon's reagent to form lactones from a primary diol.  By oxidizing one of the alcohols to an aldehyde, the second alcohol equilibrates with the aldehyde to form a lactol which is reacted quickly with more Fétizon's reagent to trap the cyclic intermediate as a lactone. This method allows for the synthesis of seven-member lactones which are traditionally more challenging to synthesize.
  Phenol functional groups can be oxidized to their respective quinone forms.  These quinones can further couple within solution producing numerous dimerizations depending upon their substituents. 
  Amines have been shown to oxidize in the presence of Fétizon's reagent to enamines and iminium cations that have been trapped, but can also be selected against in a compound with more easily oxidized alcohol functionalities.
  Fétizon's reagent can also being used to facilitate cycloaddition of a 4-hydroxy-2-furoquinilone and an olefin to form dihydrofuroquinolinones.
caption: Fetizon's reagent oxidizes phenols to quinones which can oxidatively couple to one another