Discovery and computational rationalization of diminishing alternation in [n]dendralenes

dc.contributor.authorSaglam, M.F.
dc.contributor.authorFallon, T.
dc.contributor.authorPaddon-Row, M.N.
dc.contributor.authorSherburn, M.S.
dc.date.issued2016
dc.description.abstractThe [n]dendralenes are a family of acyclic hydrocarbons which, by virtue of their ability to rapidly generate structural complexity, have attracted significant recent synthetic attention. [3]Dendralene through [8]dendralene have been previously prepared but no higher member of the family has been reported to date. Here, we describe the first chemical syntheses of the "higher" dendralenes, [9]dendralene through [12]dendralene. We also report a detailed investigation into the spectroscopic properties and chemical reactivity of the complete family of fundamental hydrocarbons, [3]dendralene to [12]dendralene. These studies reveal the first case of diminishing alternation in behavior in a series of related structures. We also report a comprehensive series of computational studies, which trace this dampening oscillatory effect in both spectroscopic measurements and chemical reactivity to conformational preferences.
dc.description.statementofresponsibilityMehmet F. Saglam, Thomas Fallon, Michael N. Paddon-Row and Michael S. Sherburn
dc.identifier.citationJournal of the American Chemical Society, 2016; 138(3):1022-1032
dc.identifier.doi10.1021/jacs.5b11889
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.orcidFallon, T. [0000-0002-6495-5282]
dc.identifier.urihttps://hdl.handle.net/2440/133327
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.relation.grantARC
dc.rights© 2015 American Chemical Society
dc.source.urihttps://doi.org/10.1021/jacs.5b11889
dc.subjectAlkenes
dc.subject.meshAlkenes
dc.subject.meshMolecular Conformation
dc.subject.meshCycloaddition Reaction
dc.titleDiscovery and computational rationalization of diminishing alternation in [n]dendralenes
dc.typeJournal article
pubs.publication-statusPublished

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