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Photochemische Reaktionen 4. Mitteilung. Beeinflussung der photochemischen Isomerisierung gekreuzter Dienone durch Substituenten am Chromophor
Author(s) -
Weinberg K.,
Utzinger E. C.,
Arigoni D.,
Jeger O.
Publication year - 1960
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.19600430132
Subject(s) - chemistry , isomerization , substituent , conjugated system , medicinal chemistry , stereochemistry , photochemistry , organic chemistry , catalysis , polymer
Irradiation of 1‐dehydro‐4‐methyl‐testosterone (IV) in dioxane solution affords as a single product an isomer, which on the basis of extensive degradation is shown to possess structure V. A similar photochemical transformation leads from 1‐dehydro‐2,4‐dimethyl‐testosterone (XXXVII) to the corresponding lumiproduct XXXVIII. Since it has been previously shown that 1‐dehydro‐testosterone (III) under the same conditions yields a mixture of 8 compounds, it appears now that the photochemical isomerisation of cross‐conjugated steroidal dienones is profoundly affected by the presence of a methyl substituent at C‐4.