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DOI: 10.1055/s-2005-872103
A Family of New 1,2,4-Trioxanes by Photooxygenation of Allylic Alcohols in Sensitizer-Doped Polymers and Secondary Reactions
Publication History
Publication Date:
29 July 2005 (online)
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Abstract
Type II photooxygenation (singlet oxygen) is described as a synthetically useful way for the preparation of allylic hydroperoxides and endoperoxides using sensitizer-adsorbed or covalently sensitizer-doped polymeric (macro- or nanosized) containers. Facilitated product separation and purification as well as increased reactivity are advantages of these techniques in comparison with solution-phase photochemistry. The products generated by Type II photooxygenation have been used for the syntheses of numerous polycyclic peroxides with a common 1,2,4-trioxane core as exhibited in the natural antimalarial artemisinin.
Key words
photochemistry - catalytic oxygenation - peroxides - peroxyacetals - Lewis acid catalysis
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References
X-ray structure analyses.
10Griesbeck, A. G.; Bartoschek, A., unpublished results.
12Griesbeck, A. G.;, Miara, C., unpublished results.
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