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

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 u...

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Published in:Organic letters 2021-05, Vol.23 (9), p.3741-3745
Main Authors: Kelly, Shane S, Shen, Tun-Li, Xian, Ming
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Language:English
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Xian, Ming
description 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.
doi_str_mv 10.1021/acs.orglett.1c01149
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title Oxygen-to-Oxygen Silyl Migration of α‑Siloxy Sulfoxides and Oxidation-Triggered Allicin Formation
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