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Type: Journal article
Title: [5]Radialene
Author: Mackay, E.
Newton, C.
Toombs-Ruane, H.
Lindeboom, E.
Fallon, T.
Willis, A.
Paddon-Row, M.
Sherburn, M.
Citation: Journal of the American Chemical Society, 2015; 137(46):14653-14659
Publisher: ACS Publications
Issue Date: 2015
ISSN: 0002-7863
Statement of
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
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.
Rights: © 2015 American Chemical Society
DOI: 10.1021/jacs.5b07445
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Chemical Engineering publications

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