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

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journal contribution
posted on 19.04.2021, 21:03 by Shane S. Kelly, Tun-Li Shen, Ming Xian
Oxidation of α-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.