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Synthesis and Structure of Corona[6](het)arenes Containing Mixed Bridge Units

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    Synthesis and Structure of Corona[6](het)arenes Containing Mixed Bridge Units
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    † Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084. China
    ‡ Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
    *[email protected]
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    Organic Letters

    Cite this: Org. Lett. 2016, 18, 11, 2668–2671
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    https://doi.org/10.1021/acs.orglett.6b01112
    Published May 16, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    A one-pot nucleophilic aromatic substitution reaction of 3,6-dichlorotetrazine with various diphenols and dibenzenethiols produced corona[4]arene[2]tetrazines that contain mixed oxygen, sulfide, methylene, and sulfone linkages. Macrocyclic ring transformations employing an inverse-electron-demand Diels–Alder reaction of tetrazine moieties with enamines and the subsequent sulfide oxidation reaction afforded diverse corona[4]arene[2]pyridazines. The acquired corona[6]arenes adopted three types of conformational structures in the crystalline state.

    Copyright © 2016 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.6b01112.

    • X-ray crystallographic files of 3–5, and 7–9 (CIF)

    • Detailed experimental procedures, characterization of all products, and 1H and 13C NMR spectra of products (PDF)

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    Cited By

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    This article is cited by 27 publications.

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    Organic Letters

    Cite this: Org. Lett. 2016, 18, 11, 2668–2671
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.6b01112
    Published May 16, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

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