Photochemische Reaktionen. 34. Mitteilung. Die Photoisomerisierung von 3‐Oxo‐Δ1;4‐Steroiden in Dioxanlösung. 3,11‐Dioxo‐17β‐acetoxy‐Δ1;4‐androstadien und 3‐Oxo‐17β‐acetoxy‐Δ1;4;9,11‐androstatrien

Ultraviolet irradiation of the steroidal cross‐conjugated dienones 3 and 7, and of the bicyclohexenone derivative 16 in dioxane solution produced the virtually quantitative isomerizations 3 → 11 (Chart 3) and 7 → 16 → 17 (Chart 6). These conversions are consistent with the previously established gen...

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Veröffentlicht in:Helvetica chimica acta 1966, Vol.49 (3), p.1183-1198
Hauptverfasser: Lorenc, Lj, Miljković, M., Schaffner, K., Jeger, O.
Format: Artikel
Sprache:eng
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Zusammenfassung:Ultraviolet irradiation of the steroidal cross‐conjugated dienones 3 and 7, and of the bicyclohexenone derivative 16 in dioxane solution produced the virtually quantitative isomerizations 3 → 11 (Chart 3) and 7 → 16 → 17 (Chart 6). These conversions are consistent with the previously established general scheme a → b → c → d → e (Chart 1). By analogy with these results, it is suggested that the photo‐isomers 9 and 10 of O‐acetylprednisone (8) represent products resulting from multiple photorearrangements rather than from direct transformations, as had been proposed in the literature.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19660490315