Tetra-tert-butyltetrahedrane

Authors

  • Prof. Dr. Günther Maier,

    1. Fachbereich Chemie der Universität, Lahnberge, D-3550 Marburg 1 (Germany)
    Current affiliation:
    1. Institut für Organische Chemie der Universität, Heinrich, Buff-Ring 58, D-6300 Lahn-Giessen (Germany)
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  • Dipl.-Chem. Stephan Pfriem,

    1. Fachbereich Chemie der Universität, Lahnberge, D-3550 Marburg 1 (Germany)
    Current affiliation:
    1. Institut für Organische Chemie der Universität, Heinrich, Buff-Ring 58, D-6300 Lahn-Giessen (Germany)
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  • Dipl.-Chem. Ulrich Schäfer,

    1. Fachbereich Chemie der Universität, Lahnberge, D-3550 Marburg 1 (Germany)
    Current affiliation:
    1. Institut für Organische Chemie der Universität, Heinrich, Buff-Ring 58, D-6300 Lahn-Giessen (Germany)
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  • Priv.-Doz. Dr. Rudolf Matusch

    Corresponding author
    1. Institut für Pharmazeutische Chemie, Marbacher Weg 6, D-3550 Marburg 1 (Germany)
    • Institut für Pharmazeutische Chemie, Marbacher Weg 6, D-3550 Marburg 1 (Germany)
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  • Small Rings, Part 25. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. We are indebted to Ms. U. Stanior for experimental assistance.—Part 24: G. Maier, S. Pfriem, Angew. Chem. 90, 551 (1978); Angew. Chem. Int. Ed. Engl. 17, 519 (1978).

Abstract

original image

The stable tetrahedrane derivative(3)—the very first alkyl-substituted tetrahedrane—has now been synthesized photochemically from the cyclopentadienone (1). 1H-NMR, 13C-NMR, mass, and IR spectra, as well as the reversible isomerization to (2), are compatible with the tetrahedrane structure. The unexpected stability of the compound is attributed to substitution of all four corners of the skeleton with bulky groups.—The starting material (1), which is also new could only be prepared under “forbidden conditions”.

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