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

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

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    24 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)1022-1032
    Number of pages11
    JournalJournal of the American Chemical Society
    Volume138
    Issue number3
    DOIs
    Publication statusPublished - 27 Jan 2016

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