Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes

Research paper by Mehmet F. Saglam, Thomas Fallon, Michael N. Paddon-Row, Michael S. Sherburn

Indexed on: 15 Jan '16Published on: 31 Dec '15Published in: Journal of the American Chemical Society


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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