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https://hdl.handle.net/2440/111876
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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 1520-5126 |
Statement of Responsibility: | 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 |
Published version: | http://dx.doi.org/10.1021/jacs.5b07445 |
Appears in Collections: | Aurora harvest 8 Chemical Engineering publications |
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