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dc.contributor.authorSaglam, M.
dc.contributor.authorAlborzi, A.
dc.contributor.authorPayne, Alan
dc.contributor.authorWillis, A.
dc.contributor.authorPaddon-Row, M.
dc.contributor.authorSherburn, M.
dc.date.accessioned2017-01-30T11:15:42Z
dc.date.available2017-01-30T11:15:42Z
dc.date.created2016-09-27T09:52:10Z
dc.date.issued2016
dc.identifier.citationSaglam, M. and Alborzi, A. and Payne, A. and Willis, A. and Paddon-Row, M. and Sherburn, M. 2016. Synthesis and Diels-Alder Reactivity of Substituted [4]Dendralenes.. Journal of Organic Chemistry. 81 (4): pp. 1461-1475.
dc.identifier.urihttp://hdl.handle.net/20.500.11937/9920
dc.identifier.doi10.1021/acs.joc.5b02583
dc.description.abstract

The first synthesis of all five possible monomethylated [4]dendralenes has been achieved via two distinct synthetic strategies. The Diels-Alder chemistry of these new dendralenes (as multidienes) with an electron poor dienophile, N-methylmaleimide (NMM), has been studied. Thus, simply upon mixing the dendralene and an excess of dienophile at ambient temperature in a common solvent, sequences of cycloadditions result in the rapid generation of complex multicyclic products. Distinct product distributions are obtained with differently substituted dendralenes, demonstrating that dendralene substitution influences the pathway followed, when a matrix of mechanistic possibilities exists. Dendralene site selectivities are traced to electronic, steric and conformational effects, thereby allowing predictive tools for applications of substituted dendralenes in future synthetic endeavors.

dc.publisherAmerican Chemical Society
dc.titleSynthesis and Diels-Alder Reactivity of Substituted [4]Dendralenes.
dc.typeJournal Article
dcterms.source.volume81
dcterms.source.number4
dcterms.source.startPage1461
dcterms.source.endPage1475
dcterms.source.titleJournal of Organic Chemistry
curtin.departmentDepartment of Chemistry
curtin.accessStatusOpen access via publisher


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