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Photochemical reactions. 132nd communication. Photochemistry of 5,6-epoxy-5,6-dihydro-7-methyl-β-ionine: Influence of a methyl group at the enone side chain on the oxirane cleavage

✍ Scribed by Antoni Siewnski; Barbara Henggeler; Hans Richard Wolf; Bruno Frei; Oskar Jeger

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
588 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

In, n *-Excitation of the y, 6-epoxy-enone (E)-3 leads exclusively to the conformers (%)-3A + B. On 'n, n*-excitation of (E)-3, in addition to (%)-3A + B, products &9 arising from a carbene intermediate e are formed. However. products of an isomerization via C(y),O-bond cleavage of the oxirane were not formed on either mode of excitation. On thermolysis, at 80" the conformer (%)-3A is transformed into (Z)-3B, which on photolysis returns to (Z)-3A and (E)-3. At 160", however, (Z)-3B rearranges to the isomers 6, 10 and 11. ') *) ' ) 4, 13 1 st Communication, see [I].

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Photochemical reactions. 133rd Communica
Photochemical reactions. 133rd Communication. Photochemistry of epoxydienes of the ionone series: Influence of a methyl group at the diene side chain on the oxirane cleavage
✍ Alfons Pascual; Takehiko Nishio; Bruno Frei; Oskar Jeger 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 German ⚖ 431 KB

On triplet excitation (h > 280 nm, acetone), the epoxydiene (E)-2 undergoes ( E ) / (Z)-isomerization exclusively, leading to the conformers (Z)-2A and (Z)-2B. On singlet excitation (h = 254 nm), apart from ( Z ) -2 A + B, the cyclobutenes 3 A + B are formed. However, the epoxydiene (E)-2 does not