Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/111876
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dc.contributor.authorMackay, E.-
dc.contributor.authorNewton, C.-
dc.contributor.authorToombs-Ruane, H.-
dc.contributor.authorLindeboom, E.-
dc.contributor.authorFallon, T.-
dc.contributor.authorWillis, A.-
dc.contributor.authorPaddon-Row, M.-
dc.contributor.authorSherburn, M.-
dc.date.issued2015-
dc.identifier.citationJournal of the American Chemical Society, 2015; 137(46):14653-14659-
dc.identifier.issn0002-7863-
dc.identifier.issn1520-5126-
dc.identifier.urihttp://hdl.handle.net/2440/111876-
dc.description.abstractThe [n]radialenes are a unique family of fundamental [n]-membered carbocyclic structures with radiating alkenes, which have attracted significant synthetic and theoretical attention. Whereas [3]-, [4]-, and [6]radialenes have been prepared and studied, all efforts to synthesize the five-membered ring compound have thus far met with failure. Here we describe the first synthesis of the fundamental hydrocarbon [5]radialene, C₁₀H₁₀. Our approach was a departure from previous radialene syntheses in that it utilized a low-temperature decomplexation of a stable organometallic compound, rather than high-temperature elimination or rearrangement. Our strategy was guided by analysis of previous radialene syntheses, which indicated rapid decomposition in oxygen, and ab initio calculations, which revealed an extraordinary susceptibility of [5]radialene to undergo Diels–Alder dimerization/polymerization. The origin of this susceptibility was traced to a small distortion energy associated with the formation of the transition structure geometry from the relaxed reactant monomers and to a narrow HOMO–LUMO gap.-
dc.description.statementofresponsibilityEmily G. Mackay, Christopher G. Newton, Henry Toombs-Ruane, Erik Jan Lindeboom, Thomas Fallon, Anthony C. Willis, Michael N. Paddon-Row and Michael S. Sherburn-
dc.language.isoen-
dc.publisherACS Publications-
dc.rights© 2015 American Chemical Society-
dc.title[5]Radialene-
dc.typeJournal article-
dc.identifier.doi10.1021/jacs.5b07445-
pubs.publication-statusPublished-
dc.identifier.orcidNewton, C. [0000-0002-8962-5917]-
dc.identifier.orcidFallon, T. [0000-0002-6495-5282]-
Appears in Collections:Aurora harvest 8
Chemical Engineering publications

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