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https://hdl.handle.net/2440/111876
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dc.contributor.author | Mackay, E. | - |
dc.contributor.author | Newton, C. | - |
dc.contributor.author | Toombs-Ruane, H. | - |
dc.contributor.author | Lindeboom, E. | - |
dc.contributor.author | Fallon, T. | - |
dc.contributor.author | Willis, A. | - |
dc.contributor.author | Paddon-Row, M. | - |
dc.contributor.author | Sherburn, M. | - |
dc.date.issued | 2015 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2015; 137(46):14653-14659 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.issn | 1520-5126 | - |
dc.identifier.uri | http://hdl.handle.net/2440/111876 | - |
dc.description.abstract | The [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.statementofresponsibility | Emily 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.iso | en | - |
dc.publisher | ACS Publications | - |
dc.rights | © 2015 American Chemical Society | - |
dc.source.uri | http://dx.doi.org/10.1021/jacs.5b07445 | - |
dc.title | [5]Radialene | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/jacs.5b07445 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Newton, C. [0000-0002-8962-5917] | - |
dc.identifier.orcid | Fallon, T. [0000-0002-6495-5282] | - |
Appears in Collections: | Aurora harvest 8 Chemical Engineering publications |
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