We have recently succeeded in preparing a series of spiro[2.5]octa-k,i'-dien-6-ones (1) and find the photochemistry oftheae ccmpowds to differ from that reported (2a-c) for the parent dienone 2 (B-c). Schuster and coworkers report that irradiation (>28&) of an ethereal solution of 2 lmds to intermed
The Photolysis of Spiro[2.5]octa-1,4-dien-3-one in Ethyl Ether. A Note on the Mechanism of Photolysis of 2,5-Cyclohexadienones
โ Scribed by Schuster, David I.; Polowczyk, Carl J.
- Book ID
- 126405422
- Publisher
- American Chemical Society
- Year
- 1964
- Tongue
- English
- Weight
- 246 KB
- Volume
- 86
- Category
- Article
- ISSN
- 0002-7863
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Irradiation of 2,4-cyclohexadienones (L) usually produces ketenes. Most commonly, these ketenes either thermally recyclize to dienone or, in the presence of nucleophiles, react to form open-chain unsaturated acids or their derivatives.lm4 In special cases, however, the ketene may thermally cyclize t
Photolysis of benzo[a]spiro [2,5]octa-1,4-dien-3-one derivative 8a afforded spiro-fused tetracycles 10 as a pair of diastereomers in 1.7:1 ratio. The photochemical process occurred by cycloaddition of the intermediate-sulfone stabilized biradical 9 to the tethered olefin. Photolysis of dienone 8b ga