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Synthesis of Polycylic Aromatic Heterocyclic Compounds via Thermal Isomerizations of 1,8-Diarylethynylnaphthalenes

Synthese von polycyclischen heteroaromatischen Verbindungen durch thermische Isomerisierung von 1,8-Diarylethinylnaphthalinen

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Summary.

 The palladium catalyzed reaction between 1,8-diiodonaphthalene and ethynylarenes affords 1,8-Bis(heteroarylethynyl)naphthalenes which can cyclize thermally via diradical intermediates to the corresponding heterocyclic acenaphthene derivatives in high yields.

Zusammenfassung.

 Es wurden über eine palladiumkatalysierte Reaktion zwischen 1,8-Diiodnaphthalin und Ethinylarenen 1,8-Bis(heteroarylethinyl)naphthaline hergestellt, welche thermisch über eine Diradikalzwischenstufe in hohen Ausbeuten zu den entsprechenden Acenaphthenderivaten cyclisieren.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Justus Liebig University, D-35392 Giessen, Germany, DE

    Thomas Eckert & Junes Ipaktschi

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  1. Thomas Eckert
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  2. Junes Ipaktschi
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Received February 26, 1998. Accepted (revised) May 4, 1998

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Eckert, T., Ipaktschi, J. Synthesis of Polycylic Aromatic Heterocyclic Compounds via Thermal Isomerizations of 1,8-Diarylethynylnaphthalenes. Monatshefte fuer Chemie 129, 1035–1048 (1998). https://doi.org/10.1007/PL00010114

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  • DOI: https://doi.org/10.1007/PL00010114

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