Photochemische Reaktionen. 95. Mitteilung. Zur Photochemie konjugierter Epoxy-enone: Die UV.-Bestrahlung von 9-Isopropyl-6-methyl-9, 10-epoxybicyclo [4.4.0] dec-1-en-3-on
✍ Scribed by Ashesh Kumar Dey; Hans Richard Wolf
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- German
- Weight
- 776 KB
- Volume
- 61
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
The Photochemistry of Conjugated Epoxy‐enones: Photolysis of 9‐Isopropyl‐6‐methyl‐9,10‐epoxybicyclo [4.4.0]dec‐l‐en‐3‐on
The title compound 1 undergoes on π, π*‐excitation vinylogous β‐cleavage of the C(γ), O‐bond and isomerizes to the unsaturated 1, 5‐diketone8(58%) and the tricyclic diketone9 (14%). On n, π*‐excitation, however, 1 undergoes only desoxygenation to the dienone 7 (ca. 15%) besides polymerization. UV.‐irradiation of 1 (λ ≥ 347 nm) in the presence of tributyl‐stannane gives 7 in 85% yield; in the presence of tributylstannane‐d~1~ 1 yields 13, the deuterated analogon of 7 (85% yield; d~1~ ca. 50%); 7 has been proven to be stable on π, π* ‐ as well as on n, π*‐excitation.