Next Article in Journal
Amifostine Protection Against Mitomycin-induced Chromosomal Breakage in Fanconi Anaemia Lymphocytes
Next Article in Special Issue
Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
Previous Article in Journal
Application of Metabolic Engineering to the Production of Scopolamine
Previous Article in Special Issue
Chemical and Enzymatic Approaches to Carbohydrate-Derived Spiroketals: Di-D-Fructose Dianhydrides (DFAs)
Article Menu

Export Article

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

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

Department of Chemistry, Institute of Organic Chemistry, Greinstr. 4, 50939 Köln, Germany
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)
View Full-Text   |   Download PDF [759 KB, uploaded 18 June 2014]   |  


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).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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[]hexadecanes: Novel Spirofused Bis-Trioxane Peroxides. Molecules 2008, 13, 1743-1758.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top