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 |
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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
- Organic Chemistry
- Drug Discovery
Cite this
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. / Kamata, Masaki; Ohta, Motoko; Komatsu, Ken Ichi; Kim, Hye-Sook; Wataya, Yusuke.
In: Tetrahedron Letters, Vol. 43, No. 11, 11.03.2002, p. 2063-2067.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes
T2 - Direct evidence for nucleophilic O-1,2-aryl shifts
AU - Kamata, Masaki
AU - Ohta, Motoko
AU - Komatsu, Ken Ichi
AU - Kim, Hye-Sook
AU - Wataya, Yusuke
PY - 2002/3/11
Y1 - 2002/3/11
N2 - 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.
AB - 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.
KW - 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes
KW - Antimalarial activity
KW - Cyclic peroxides
KW - FeBr
KW - Fragmentation
KW - O-1,2-aryl shift
KW - Reaction mechanism
KW - Rearrangement
UR - http://www.scopus.com/inward/record.url?scp=0037060948&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037060948&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(02)00166-1
DO - 10.1016/S0040-4039(02)00166-1
M3 - Article
AN - SCOPUS:0037060948
VL - 43
SP - 2063
EP - 2067
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 11
ER -