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Molecules 2008, 13(8), 1743-1758; doi:10.3390/molecules13081743
Article

1,2,5,10,11,14-Hexaoxadispiro[5.2.5.2]hexadecanes: Novel Spirofused Bis-Trioxane Peroxides

1,* , 1, 1, 1, 1,*  and 2
1 Department of Chemistry, Institute of Organic Chemistry, Greinstr. 4, 50939 Köln, Germany 2 Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt
* Authors to whom correspondence should be addressed.
Received: 28 July 2008 / Revised: 15 August 2008 / Accepted: 18 August 2008 / Published: 19 August 2008
(This article belongs to the Special Issue Spiro Compounds)
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Abstract

A set of new bis-spirofused 1,2,4-trioxanes 4a-d was obtained from the reaction of cyclohexane-1,4-dione with allylic hydroperoxides 2a-d, bearing an additional hydroxy group in the homoallylic position, by diastereoselective photooxygenation of allylic alcohols 1a-d and subsequent BF3-catalyzed peroxyacetalization with the diketone. From the reaction of a monoprotected cyclohexane-1,4-dione 5 with the allylic hydroperoxide 6 derived from the singlet oxygenation of methyl hydroxytiglate, one monospiro compound was obtained, the 1,2,4-trioxane ketone 7, as well as a mixture of the diastereoisomeric syn- and anti bis-1,2,4-trioxanes 8. The structures of bis-1,2,4-trioxanes were examined theoretically by DFT methods and compared with X-ray structural data in order to evaluate the preferential trioxane ring conformational orientation.
Keywords: Bis-spiro compounds; peroxides; singlet oxygen; DFT calculations; X-ray structure determination. Bis-spiro compounds; peroxides; singlet oxygen; DFT calculations; X-ray structure determination.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Griesbeck, A.G.; Höinck, L.-O.; Lex, J.; Neudörfl, J.; Blunk, D.; El-Idreesy, T.T. 1,2,5,10,11,14-Hexaoxadispiro[5.2.5.2]hexadecanes: Novel Spirofused Bis-Trioxane Peroxides. Molecules 2008, 13, 1743-1758.

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