Fétizon oxidation

Its great reactivity with lactols makes the Fétizon oxidation a useful method to obtain lactones from a diol.

[4] The rate limiting step of this reaction is proposed to be the initial association of the alcohol to the silver ions.

[5] Additional polar functionalities of the reactant should also be avoided whenever possible as even the presence of an alkene can sometimes reduce the reactivity of a substrate 50 fold.

[5] Tertiary alcohols lacking an alpha hydrogen are selected against and generally do not oxidize in the presence of Fétizon's reagent.

However, increasing the amount of celite past 900 grams per mole of silver(I) carbonate begins to slow the reaction due to dilution effects.

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.

[15] As Fétizon's oxidation is a neutral reaction, acid and base sensitive protecting groups are also compatible with the reagent and by products generated.

[16] Halohydrins that possess a trans stereochemistry have been demonstrated to form epoxides and transposed products in the presence of Fétizon's reagent.

Silver carbonate on celite oxidizes alcohols through single electron oxidation by the silver cations
Even weakly associating functionalities such as olefins can interfere with the association of the reactant alcohol with Fetizon's reagent
The oxidation of an alcohol with an alpha hydrogen sterically hindered by axial hydrogens proceeds slower with Fetizon's reagent
Fetizon's reagent oxidizes secondary alcohols selectively in the presence of tertiary alcohols
Fetizon's reagent is capable of monooxidizing a symmetric diol
Fetizon's reagent oxidize lactols into lactones
Treatment of a terminal diol with Fetizon's reagent can result in lactone formation
Fetizon's reagent oxidizes phenols to quinones which can oxidatively couple to one another
A tertiary propargylic alcohol is fragmented upon treatment with Fetizon's reagent
Trans-halohydrins can transpose or form epoxides upon treatment with Fetizon's reagent
Upon oxidation with Fetizon's reagent, a 1,3 diol may eliminate water to produce an enone