Singlet oxygen addition to homoallylic substrates in solution and microemulsion: novel secondary reactions |
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Authors: | Axel G Griesbeck Miyeon Cho |
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Institution: | Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany |
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Abstract: | The photooxygenation of three homoallylic substrates, the γ,δ-unsaturated ketone 1a, nitrile 2a, and the γ,δ-unsaturated ester 3a was investigated in homogeneous solution and in microemulsion (for 1a). Two secondary reaction pathways were detected for the allylic hydroperoxides of type b and c, respectively. The cyclization reactions of 1b and 2b to the 1,2-dioxanes 1d and 2d followed well-known reaction patterns, whereas the base-catalyzed epoxide (1e-3e) formation from the tertiary allylic hydroperoxides 1c-3c is a unprecedented reaction type. |
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Keywords: | Ene reaction Singlet oxygen Homoallylic substrates Rearrangement |
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