Pyramidalized double bonds containing endoperoxide linkages: photooxygenation of dimethyl cis-3,8-dihydroheptalene-3,8, dicarboxylate

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dc.citation.epage6676en_US
dc.citation.issueNumber18en_US
dc.citation.spage6670en_US
dc.citation.volumeNumber64en_US
dc.contributor.authorSaraçoǧlu, N.en_US
dc.contributor.authorMenzek, A.en_US
dc.contributor.authorSayan, Ş.en_US
dc.contributor.authorSalzner, U.en_US
dc.contributor.authorBalci, M.en_US
dc.date.accessioned2016-02-08T10:40:52Z
dc.date.available2016-02-08T10:40:52Z
dc.date.issued1999en_US
dc.departmentDepartment of Chemistryen_US
dc.description.abstractDiels-Alder cycloaddition utilizing singlet oxygen as the dienophile with dimethyl cis-3,8-dihydroheptalene-3,8-dicarboxylate (5) has been investigated, and monoaddition product 7 has been isolated. The addition of a second singlet oxygen to the cycloheptatriene unit in 7 gave syn- bis(norcaradiene) bis(endoperoxide) 4. 1H NMR spectral studies and theoretical calculations indicate the increased pyramidalization in syn-4 compared with carbon analogue. The increased pyramidalization results from hyperconjugation between the central π-bond and the four adjacent C-O bonds and by rehybridization at C3, C4, C5, and C6. Furthermore, the increased reactivity for syn-4, which is probably arising from further folding of the central double bond, is also in agreement with theoretical calculations.en_US
dc.identifier.doi10.1021/jo990393oen_US
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/11693/25209
dc.language.isoEnglishen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/jo990393oen_US
dc.source.titleJournal of Organic Chemistryen_US
dc.subjectDimethyl 3,8 dihydroheptalene 3,8 dicarboxylateen_US
dc.subjectEndoperoxideen_US
dc.subjectUnclassified drugen_US
dc.subjectChemical bindingen_US
dc.subjectConjugationen_US
dc.subjectDecarboxylationen_US
dc.subjectPeroxidationen_US
dc.subjectProton nuclear magnetic resonanceen_US
dc.subjectReaction analysisen_US
dc.subjectStructure analysisen_US
dc.titlePyramidalized double bonds containing endoperoxide linkages: photooxygenation of dimethyl cis-3,8-dihydroheptalene-3,8, dicarboxylateen_US
dc.typeArticleen_US

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