Synthesis and Transformation of Radialenes

Maas, Gerhard; Hopf, Henning

doi:10.1002/9780470682531.pat0117

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2016

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“…The radialenes are also relatively poorly investigated, with only the triene, tetraene, pentaene, and hexaene reported in the literature. In contrast, the unbranched systems have received significant attention, which is unsurprising when the number of natural products containing linear polyenic and annulenic systems is considered.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2016

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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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