Discovery and computational rationalization of diminishing alternation in [n]dendralenes
dc.contributor.author | Saglam, M.F. | |
dc.contributor.author | Fallon, T. | |
dc.contributor.author | Paddon-Row, M.N. | |
dc.contributor.author | Sherburn, M.S. | |
dc.date.issued | 2016 | |
dc.description.abstract | The [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.statementofresponsibility | Mehmet F. Saglam, Thomas Fallon, Michael N. Paddon-Row and Michael S. Sherburn | |
dc.identifier.citation | Journal of the American Chemical Society, 2016; 138(3):1022-1032 | |
dc.identifier.doi | 10.1021/jacs.5b11889 | |
dc.identifier.issn | 0002-7863 | |
dc.identifier.issn | 1520-5126 | |
dc.identifier.orcid | Fallon, T. [0000-0002-6495-5282] | |
dc.identifier.uri | https://hdl.handle.net/2440/133327 | |
dc.language.iso | en | |
dc.publisher | American Chemical Society | |
dc.relation.grant | ARC | |
dc.rights | © 2015 American Chemical Society | |
dc.source.uri | https://doi.org/10.1021/jacs.5b11889 | |
dc.subject | Alkenes | |
dc.subject.mesh | Alkenes | |
dc.subject.mesh | Molecular Conformation | |
dc.subject.mesh | Cycloaddition Reaction | |
dc.title | Discovery and computational rationalization of diminishing alternation in [n]dendralenes | |
dc.type | Journal article | |
pubs.publication-status | Published |