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|Citation:||Journal of the American Chemical Society, 2015; 137(46):14653-14659|
|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 -, -, and 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 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 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|
|Appears in Collections:||Chemical Engineering publications|
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