Journal of Organic Chemistry p. 1631 - 1635 (1991)
Update date:2022-08-02
Topics:
Hasegawa, Eietsu
Ishiyama, Kenyuki
Horaguchi, Takaaki
Shimizu, Takahachi
Photoinduced single electron transfer (SET) reactions of α,β-epoxy ketones have been studied using alkylamine electron donors.Irradiation of chalcone epoxide 1 with triethylamine (TEA) afforded β-diketone 2 and β-hydroxy ketne 3.Photoreaction of 1 with TEA in MeOH resulted in a slightly increased product ratio (3/2) compared with that in MeCN.When 1,4-diazabicyclo<2.2.2>octane (DABCO) was used instead of TEA, a decrease in the yield of 3 was observed.Only 2 was obtained on irradiation of a solution of 1 in TEA and MeCN containing LiClO4.Studies of photoreactions of dypnone epoxide 9, benzoylisopropylethylene epoxide 12, and acrylophenone epoxide 15 indicate that the nature of β-substituent also influences the product distribution.It was also found that 1,6-bis(dimethylamino)pyrene (BDMAP) sensitizes the photoreaction of 1 in the presence of TEA to produce 2.Based on the results obtained, a reaction mechanism involving selective Cα-O bond cleavage of intermediate α,β-epoxy ketone anion radicals is proposed.
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