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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
Received: 28 July 2008; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Griesbeck AG, Höinck L-O, Lex J, Neudörfl J, Blunk D, El-Idreesy TT. 1,2,5,10,11,14-Hexaoxadispiro[5.2.5.2]hexadecanes: Novel Spirofused Bis-Trioxane Peroxides. Molecules. 2008; 13(8):1743-1758.

Chicago/Turabian Style

Griesbeck, Axel G.; Höinck, Lars-Oliver; Lex, Johann; Neudörfl, Jörg; Blunk, Dirk; El-Idreesy, Tamer T. 2008. "1,2,5,10,11,14-Hexaoxadispiro[5.2.5.2]hexadecanes: Novel Spirofused Bis-Trioxane Peroxides." Molecules 13, no. 8: 1743-1758.


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