Tetravinylallene

Cecile Elgindy, Jas S. Ward, Michael S. Sherburn*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    7 Citations (Scopus)

    Abstract

    The first chemical synthesis of tetravinylallene (3,5-divinylhepta-1,3,4,6-tetraene) is reported. The final, key step of the synthesis involves a palladium-catalyzed, Negishi-type cross-coupling involving 1,5-transposition of a penta-2-en-4-yn-1-ol methanesulfonate. The unprecedented fundamental hydrocarbon is sufficiently stable to be purified by flash chromatography. A similar synthetic pathway grants access to the first substituted tetravinylallenes, which provide insights into the influence of substitution upon stability and reactivity. Tetravinylallenes are shown to break new ground in swift structural complexity creation, with three novel sequences reported.

    Original languageEnglish
    Pages (from-to)14573-14577
    Number of pages5
    JournalAngewandte Chemie - International Edition
    Volume58
    Issue number41
    DOIs
    Publication statusPublished - 7 Oct 2019

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