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Photochemische Reaktionen. 26. Mitteilung . Zur UV.‐Bestrahlung von O‐Acety1‐1‐dehydro‐2‐methyl‐testosteron. (Vorläufige Mitteilung)
Author(s) -
Ganter C.,
Greuter F.,
Kägi D.,
Schaffner K.,
Jeger O.
Publication year - 1964
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19640470228
Subject(s) - chemistry , irradiation , stereochemistry , sequence (biology) , testosterone (patch) , medicinal chemistry , biochemistry , physics , nuclear physics , biology , genetics
The ultra‐violet irradiation of O‐acetyl‐1‐dehydro‐2‐methyl‐testosterone ( 1 ) in dioxane solution leads to a mixture of ketonic and phenolic isomers from which five components ( 2 – 6 ) have been isolated. The structures of ketones 2 and 4 have been established. The sequence of photochemical rearrangements is 1 → 2 → 3 . Evidence points to the intermedi acyof an isomer of type e and the formation of compounds 4 and 5 from 3 . Structural formulas for 3 (= g ) and 5 (= j ) are advanced on this basis. The close relationship between the sequences of rearrangements initiated by the irradiation of O‐acetyl‐1‐dehydro‐testosterone and its 2‐methyl homologue ( 1 ), respectively, is discussed.