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- Title
Photochemische Reaktionen 42. Mitteilung [1]. Photoisomerisierung von α, β-Epoxyketonen II Der sterische Verlauf der Umlagerung von 3-Oxo-4, 5-oxido-Steroiden.
- Authors
Wehrli, H.; Lehmann, C.; Iizuka, T.; Schaffner, K.; Jeger, O.
- Abstract
The photorearrangement previously described [3] of saturated and Δ1-unsaturated 3-oxo-4,5-epoxy-10β-steroids to 3,5-dioxo-10(5 →4)- abeo compounds proceeds most likely via a radical 1,2-alkyl shift (Chart 1). The similar rearrangements of the related 10α-epoxyketone 10 and the 4-methyl-epoxyketones 13, 15, 16, 20 and 21 to the corresponding 3,5-diketones occurred without epimerization at the migrating carbon atom (C-10) and the site of substitution (C-4) (Chart 3). The stereochemical control of the rearrangement is in agreement with the earlier proposed mechanism of a concerted alkyl radical shift in these alicyclic systems.
- Publication
Helvetica Chimica Acta, 1967, Vol 50, Issue 8, p2403
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19670500827