Journal of the Chemical Society. Perkin transactions I p. 471 - 476 (1994)
Update date:2022-08-17
Topics:
Suginome, Hiroshi
Kamekawa, Hisato
Sakurai, Hideo
Konishi, Atsushi
Senboku, Hisanori
Kobayashi, Kazuhiro
The irradiation of 2-hydroxyphenanthrene-1,4-dione and various electron-rich alkenes such as ethyl vinyl ether, isobutene, 1-methoxycyclohexene and 3,4-dihydro-2H-pyran in acetone with Pyrex-filtered light gave 9,10-dihydrophenanthro<2,3-b>furan-7,11-diones arising from regioselective <3 + 2> photoaddition in 25 - 50percent yields.A <3 + 2> photoadduct, 9-phenylphenanthro<2,3-b>furan-7,11-dione, can be similarly formed in low yield when 2-hydroxyphenanthrene-1,4-dione and phenylacetylene in acetone are irradiated with Pyrex-filtered light.In contrast, the irradiation of 2-hydroxyphenanthrene-1,4-dione and alkenes such as methyl acrylate, acrylonitrile, cyclohexene, isopropenyl acetate, propenyl acetate, vinyl acetate, 1-phenylprop-1-yne or trimethylsilylacetylene in acetone gave only a dimer in 42-52percent yields, no <3 + 2> photoadducts being formed.
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