Walk Rearrangement in the 1,2,3,4-Tetra-tert-butylhydroxycyclobutenylium Ion

Authors

  • Prof. Dr. Günther Maier,

    Corresponding author
    1. Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, D-6300 Giessen (FRG)
    • Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, D-6300 Giessen (FRG)
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  • Dipl.-Chem. Rolf Emrich,

    1. Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, D-6300 Giessen (FRG)
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  • Dr. Hans-Otto Kalinowski

    1. Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, D-6300 Giessen (FRG)
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  • Small Rings, Part 56. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.—Part 55; G. Maier, M. Hoppe, K. Lanz, H. P. Reisenauer, Tetrahedron Lett. 25 (1984) 5645.

Abstract

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Contrary to the predictions of the Woodward-Hoffmann rules, the walk rearrangement (1) proceeds with inversion at the migrating C atom. The cause is an unusually strongly pronounced secondary orbital interaction.

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