Source:http://linkedlifedata.com/resource/pubmed/id/18794783
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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
8
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pubmed:dateCreated |
2008-9-16
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pubmed:abstractText |
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 BF(3)-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.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Cyclohexane,
http://linkedlifedata.com/resource/pubmed/chemical/Cyclohexanes,
http://linkedlifedata.com/resource/pubmed/chemical/Heterocyclic Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Hydrogen Peroxide,
http://linkedlifedata.com/resource/pubmed/chemical/Peroxides,
http://linkedlifedata.com/resource/pubmed/chemical/Spiro Compounds
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pubmed:status |
MEDLINE
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pubmed:issn |
1420-3049
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pubmed:author | |
pubmed:issnType |
Electronic
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pubmed:volume |
13
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1743-58
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pubmed:dateRevised |
2009-10-27
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pubmed:meshHeading | |
pubmed:year |
2008
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pubmed:articleTitle |
1,2,5,10,11,14-hexaoxadispiro[5.2.5.2]hexadecanes: novel spirofused bis-trioxane peroxides.
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pubmed:affiliation |
Department of Chemistry, Institute of Organic Chemistry, Greinstr. 4, 50939 Köln, Germany. griesbeck@uni-koeln.de
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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