Oxygen-to-Oxygen Silyl Migration of α-Siloxy Sulfoxides and Oxidation-Triggered Allicin Formation

Oxidation of alpha-siloxy thioethers leads to the formation of the corresponding sulfoxides as unstable intermediates, which undergo an intramolecular oxygen-to-oxygen silyl migration to break the C-S linkage. This process produces silyl protected sulfenic acids and subsequently thiosulfinates. It was used to develop oxidation-triggered allicin donors.

Automated summary

Oxidation of alpha-siloxy thioethers results in the formation of unstable sulfoxides, which then undergo intramolecular oxygen-to-oxygen silyl migration to break the C-S linkage, producing silyl protected sulfenic acids and thiosulfinates. This process is utilized for developing oxidation-triggered allicin donors.