Ozonolysis of bicyclic 1,2-dioxines: Initial scope and mechanistic insights

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dc.contributor.authorCain, N.
dc.contributor.authorTiekink, E.
dc.contributor.authorTaylor, D.
dc.date.issued2012
dc.description.abstractThe ozonolysis of bicyclic 1,2-dioxines was investigated using a variety of 1,4-disubstituted 1,2-dioxines along with a 1,3-dialkyl and steroidal example, with yields ranging from moderate to excellent. Two different pathways were observed upon reaction of the 1,4-disubstituted 1,2-dioxines with ozone; one pathway saw the "expected" results, that is, cleavage of the olefinic moiety with generation of 1,4-dicarbonyl 1,2-dioxines, while the other pathway revealed a previously unobserved rearrangement involving cleavage of the peroxide linkage along with loss of either CO or CO(2). Several unsymmetrical ozonolyses were also performed to further investigate the origins of this rearrangement, and initial mechanistic insights into the fragmentation pathways are discussed.
dc.description.statementofresponsibilityNicole M. Cain, Edward R. T. Tiekink, and Dennis K. Taylor
dc.identifier.citationJournal of Organic Chemistry, 2012; 77(8):3808-3819
dc.identifier.doi10.1021/jo3001518
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.orcidTaylor, D. [0000-0002-3302-4610] [0000-0002-4274-3983] [0000-0003-0633-7424]
dc.identifier.urihttp://hdl.handle.net/2440/71314
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.rightsCopyright © 2012 American Chemical Society
dc.source.urihttps://doi.org/10.1021/jo3001518
dc.subjectOzone
dc.subjectDioxins
dc.subjectMolecular Structure
dc.subjectBridged Bicyclo Compounds
dc.titleOzonolysis of bicyclic 1,2-dioxines: Initial scope and mechanistic insights
dc.typeJournal article
pubs.publication-statusPublished

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