Structure of a Chiral Lithium Azaenolate: Monomeric, Intramolecular Chelated Lithio-2-acetylnaphthalene-SAMP-hydrazone

Authors

  • Prof. Dr. Dieter Enders,

    Corresponding author
    1. Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-5100 Aachen (FRG)
    • Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-5100 Aachen (FRG)
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  • Dipl.-Chem. Gerhard Bachstädter,

    1. Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-5100 Aachen (FRG)
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  • Dr. Kenneth A. M. Kremer,

    1. Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-5100 Aachen (FRG)
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    • Alexander-von-Humboldt Scholarship, 1982–1984.

  • Michael Marsch,

    1. Fachbereich Chemie der Universität, Hans-Meerwein-Strasse, D-3550 Marburg (FRG)
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  • Dr. Klaus Harms,

    1. Fachbereich Chemie der Universität, Hans-Meerwein-Strasse, D-3550 Marburg (FRG)
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  • Prof. Dr. Gernot Boche

    Corresponding author
    1. Fachbereich Chemie der Universität, Hans-Meerwein-Strasse, D-3550 Marburg (FRG)
    • Fachbereich Chemie der Universität, Hans-Meerwein-Strasse, D-3550 Marburg (FRG)
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  • This work was supported by the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft. We thank Degussa AG and BASF AG for gifts of chemicals.

Abstract

original image

A more detailed insight into the structure of the 1-azaallyl anion of a SAMP-hydrazone has been made possible by the first X-ray crystallographic study of a chiral monomeric azaenolate. The lithiated 2-acetylnaphthalene-SAMP-hydrazone 1 exists as rubyred crystals; it has an η1-structure with intramolecular methoxychelatization, while the lithium ion is solvated by two THF molecules.

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