Discovery and computational rationalization of diminishing alternation in [n]dendralenes

Date

2016

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Saglam, M.F.
Fallon, T.
Paddon-Row, M.N.
Sherburn, M.S.

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Journal of the American Chemical Society, 2016; 138(3):1022-1032

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Mehmet F. Saglam, Thomas Fallon, Michael N. Paddon-Row and Michael S. Sherburn

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Abstract

The [n]dendralenes are a family of acyclic hydrocarbons which, by virtue of their ability to rapidly generate structural complexity, have attracted significant recent synthetic attention. [3]Dendralene through [8]dendralene have been previously prepared but no higher member of the family has been reported to date. Here, we describe the first chemical syntheses of the "higher" dendralenes, [9]dendralene through [12]dendralene. We also report a detailed investigation into the spectroscopic properties and chemical reactivity of the complete family of fundamental hydrocarbons, [3]dendralene to [12]dendralene. These studies reveal the first case of diminishing alternation in behavior in a series of related structures. We also report a comprehensive series of computational studies, which trace this dampening oscillatory effect in both spectroscopic measurements and chemical reactivity to conformational preferences.

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© 2015 American Chemical Society

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