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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| Veröffentlicht in: | Organic letters 2021-05, Vol.23 (9), p.3741-3745 |
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| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | 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. |
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| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/acs.orglett.1c01149 |