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Synthesis 2002(12): 1711-1715
DOI: 10.1055/s-2002-33637
DOI: 10.1055/s-2002-33637
PAPER
© Georg Thieme Verlag Stuttgart · New York
Chemistry of 1,2,4-Trioxanes: Metal-Induced Deoxygenation and Rearrangement of the 1,2,4-Trioxane Obtained by Photooxidation of β-Ionone
Weitere Informationen
Received
19 February 2002
Publikationsdatum:
05. September 2002 (online)
Publikationsverlauf
Publikationsdatum:
05. September 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200212/lookinside/thumbnails/10.1055-s-2002-33637-1.jpg)
Abstract
The reactivity of 2,2,6,8-tetramethyltricyclo(6.2.2.01,6)dodecene (2) toward different metal salts has been explored. In the presence of Fe(II), Sn(II) and Ce(IV) ions, compound 2 underwent a rearrangement process to afford acyclic triketones Z-3 and E-3. The action of Zn powder in acetic acid resulted in an unexpected formation of furan 4 in high yield.
Key words
peroxides - trioxanes - furans - rearrangements - deoxygenation
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References
This yield is a great improvement compared with that previously reported [10] (3% yield).