Oxidation of thiacyclopentanone-2 with hydrogen peroxide gave γ, γ'-dithiodibutyric acid (1), dibutyric acid thiolsulfonate (2), and γ, γ'-sulfonyldibutyric acid (3) in 81%, 60% and 59% yields, respectively, under various reaction conditions.
As an intermediate of this reaction, γ-mercaptobutyric acid was isolated.
When the oxidation was carried out with dry chlorine gas or triacetone superoxide, only (1) was obtained in good yield and (2) and (3) was not detected.
These results show that, the reaction of thiacyclopentanone-2 with hydrogen peroxide initially forms γ-mercaptobutyric acid, which is further oxidized to (3) via (1) and (2).
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