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Photochemical Reactions. Part 60 [1]. The photorearrangement of a 2, 5-diene-1, 7-dione

✍ Scribed by S. Domb; K. Schaffner

Publisher: John Wiley and Sons
Year: 1970
Tongue: German
Weight: 917 KB
Volume: 53
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19700530725

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✦ Synopsis

hv 11 hv 0 a? 6 0 @ ' o hv po + Po 0 0 0 9 10 Chart 2. R 0 0 0 8 R -t i 11 R = Br 12 Ultraviolet Irradiation of 3,7-Dioxo-4,4-dimethyl-17~-acetoxy-A1~5-androstadiene (12); Results.

-Irradiations on an analytical scale of 12 in dioxane and acetonitrile with wavelengths of both 2537 h; and >3400 A, and in benzene with 3400 A, gave in each case the same two products. Periodical analyses by thin-layer chromatography revealed that the formation of one product (13) sets in prior to the formation of the other one (14). In a preparative irradiation experiment, using a 1.7 x 1 0 -2 ~ benzene solution of 12 and wavelengths of > 3400 h;, 40% of photoproduct 13, 11% of the isomer 14, and lSyo of unreacted starting material (12) were isolated in chromatographically pure form.

Irradiations with 2537 A of the photoproducts in dioxane solutions and analysis by thin-layer chromatography indicated that 13 isomerized to 14, and that 14 converted

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