A Novel Reactivity of SeO2 with 1,3-Dienes: Formation of syn 1,2- and 1,4-Diols via a Facile C−Se Bond Oxidation
A novel reaction between 1,3-dienes and selenium dioxide to give syn 1,2- and 1,4-diol cyclic selenites was studied in detail. This study indicates that an initial concerted [4 + 2] cycloaddition followed by a stereospecific carbon−selenium bond oxidation is involved in this unprecedented syn dihydr...
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| Veröffentlicht in: | Organic letters 2001-10, Vol.3 (20), p.3161-3163 |
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| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | A novel reaction between 1,3-dienes and selenium dioxide to give syn 1,2- and 1,4-diol cyclic selenites was studied in detail. This study indicates that an initial concerted [4 + 2] cycloaddition followed by a stereospecific carbon−selenium bond oxidation is involved in this unprecedented syn dihydroxy addition reaction mediated by selenium dioxide. |
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| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/ol016462e |