Synthesis of m -terphenyl derivatives via domino Diels-Alder/Retro-Diels- Alder reaction of 1,3-dienic δ-sultones with alkynes

Jens Gaitzsch, Victor Rogachev, Martin Zahel, Peter Metz

    Research output: Contribution to journalArticle

    3 Citations (Scopus)

    Abstract

    A highly regioselective synthetic method based on the domino Diels-Alder/retro-Diels-Alder reaction (DA/RDA) of 1,3-dienic δ-sultones with alkynes provides substituted m-terphenyls by elimination of SO3. A variety of δ-sultones and alkynes were examined to determine the scope of the reaction. The de novo synthesized aromatic products were obtained using thermal, microwave, and high-pressure activation.

    Original languageEnglish
    Article numberSS-2013-Z0580-OP
    Pages (from-to)531-536
    Number of pages6
    JournalSynthesis (Germany)
    Volume46
    Issue number4
    DOIs
    Publication statusPublished - Feb 2014

    Fingerprint

    Alkynes
    Chemical activation
    Microwaves
    Derivatives
    naphthosultone
    Hot Temperature

    Keywords

    • alkynes
    • Diels-Alder reaction
    • high pressure
    • m -terphenyls
    • sultones

    ASJC Scopus subject areas

    • Organic Chemistry
    • Catalysis

    Cite this

    Synthesis of m -terphenyl derivatives via domino Diels-Alder/Retro-Diels- Alder reaction of 1,3-dienic δ-sultones with alkynes. / Gaitzsch, Jens; Rogachev, Victor; Zahel, Martin; Metz, Peter.

    In: Synthesis (Germany), Vol. 46, No. 4, SS-2013-Z0580-OP, 02.2014, p. 531-536.

    Research output: Contribution to journalArticle

    Gaitzsch, Jens ; Rogachev, Victor ; Zahel, Martin ; Metz, Peter. / Synthesis of m -terphenyl derivatives via domino Diels-Alder/Retro-Diels- Alder reaction of 1,3-dienic δ-sultones with alkynes. In: Synthesis (Germany). 2014 ; Vol. 46, No. 4. pp. 531-536.
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