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Synthesis 2005(14): 2433-2444  
DOI: 10.1055/s-2005-872103
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York

A Family of New 1,2,4-Trioxanes by Photooxygenation of Allylic Alcohols in Sensitizer-Doped Polymers and Secondary Reactions

Anna Bartoschek, Tamer T. El-Idreesy, Axel G. Griesbeck*, Lars-Oliver Höinck, Johann Lex, Claus Miara, Jörg M. Neudörfl
University of Cologne, Institute of Organic Chemistry, Greinstr. 4, 50939 Köln, Germany
Fax: +49(221)4705057; e-Mail: griesbeck@uni-koeln.de;
Further Information

Publication History

Received 13 May 2005
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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1

X-ray structure analyses.

10

Griesbeck, A. G.; Bartoschek, A., unpublished results.

12

Griesbeck, A. G.;, Miara, C., unpublished results.

14

Griesbeck, A. G.; Höinck, L.-O., unpublished results.

28

Griesbeck, A. G.; El-Idreesy, T. T., unpublished results.