Abstract
1,5-Diaryl-6,7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph, 1c: Ar=p-MeC6H4, 1d: Ar=p-MeOC6H4) were prepared by a modified method of photo-electron transfer oxygenation, and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(II)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products, 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated.
| Original language | English |
|---|---|
| Pages (from-to) | 2063-2067 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 43 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - Mar 11 2002 |
Keywords
- 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes
- Antimalarial activity
- Cyclic peroxides
- FeBr
- Fragmentation
- O-1,2-aryl shift
- Reaction mechanism
- Rearrangement
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Kamata, M., Ohta, M., Komatsu, K. I., Kim, H. S., & Wataya, Y. (2002). Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: Direct evidence for nucleophilic O-1,2-aryl shifts. Tetrahedron Letters, 43(11), 2063-2067. https://doi.org/10.1016/S0040-4039(02)00166-1