Photochemical transformations of protonated phenols. A one-step synthesis of umbellulone from thymol

P Baeckstroem, U Jacobsson, B Koutek…

文献索引：Baeckstroem, Peter; Jacobsson, Ulla; Koutek, Bohumir; Norin, Torbjoern Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3728 - 3732

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被引用次数: 18

摘要

UV irradiation of thymol (7) at 254 or 300 nm in trifluoromethanesulfonic acid affords ten products, eight of which have been isolated and characterized. Four competitive processes are suggested to be operating in the formation of the photoproducts:(i) regioselective type A rearrangement leading to umbellulone (8, about lo%),(ii) formal C2-C3 migration by type A rearrangement and ring opening which affords the principal product, 3-isopropyl-5- ...

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