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Peroxylactone
The organic functional group peroxylactone is a heterocyclic organic compound consisting of a five member ring with two adjacent oxygens (peroxide) and three carbon lactone. This group is commonly formed upon peroxidation of alpha keto acids.

Mechanism
Phenylpyruvic acid is a classical example of a keto acid that forms a peroxylactone intermediate. Initially the carbonyl at the alpha keto position tautomerizes to form a reactive enol. Peroxidation occurs at the benzylic carbon to either react with the alpha position to form a 1,2-Dioxetane, or, the peroxide reacts with the carboxylic acid to for a peroxylactone (alpha-keto-beta-peroxylactone). The pathways compete. In the case of phenylpyruvate, both pathways form benzaldehyde. The dioxetane forms oxalic acid, whereas the peroxylactone forms carbon dioxide and carbon monoxide.

History
The peroxylactone group was first described by Mayers and Kagan in 1974.

Applications
The peroxylactone mechanism is a potential source for endogenous gasotransmitters and prodrug scaffold.