✦ LIBER ✦
Singlet oxygen addition to homoallylic substrates in solution and microemulsion: novel secondary reactions
✍ Scribed by Axel G. Griesbeck; Miyeon Cho
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 166 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The photooxygenation of three homoallylic substrates, the c,d-unsaturated ketone 1a, nitrile 2a, and the c,d-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.