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- W2952510193 abstract "The photooxygenation of 1,4-cyclohexadiene (3) affords the diastereomeric hydroperoxy endoperoxides exo-4 and endo-4 and the diastereomeric hydroperoxides trans-5 and cis-5 in a ratio of 87:9:3.5:0.5. Selective reduction of hydroperoxide group in the endoperoxides exo-4 and endo-4 in the presence of titanium tetraisopropoxide−diethyl sulfide gave the corresponding hydroxy endoperoxides exo-7 and endo-7, which on PCC oxidation leads to the phenol-derived keto endoperoxide 2. The triphenylphosphine deoxygenation of the keto endoperoxide 2 produces a 9:1 mixture of 1,2- and 1,4-dihydroxybenzenes 10 and 11, while the CoTPP-catalyzed rearrangement affords the bisepoxide 12, malealdehyde (13), and β-lactone 14. The mechanisms of these transformations are presented." @default.
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- W2952510193 date "2000-08-25" @default.
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- W2952510193 title "2,3-Dioxabicyclo[2.2.2]oct-7-en-5-one: Synthesis and Reactions of the Keto Endoperoxide of Phenol" @default.
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- W2952510193 doi "https://doi.org/10.1021/jo000120p" @default.
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