A General Procedure for Generating Conjugated 1,x Dipoles

Authors

  • Priv.-Doz. Dr. Klaus Burger,

    Corresponding author
    1. Institut für Organische Chemie der Technischen Universität, Arcisstrasse 21, D-8000 München 2 (Germany)
    • Institut für Organische Chemie der Technischen Universität, Arcisstrasse 21, D-8000 München 2 (Germany)
    Search for more papers by this author
  • Dr. Helmut Schickaneder,

    1. Institut für Organische Chemie der Technischen Universität, Arcisstrasse 21, D-8000 München 2 (Germany)
    Search for more papers by this author
  • Dipl.-Chem. Claus Zettl

    1. Institut für Organische Chemie der Technischen Universität, Arcisstrasse 21, D-8000 München 2 (Germany)
    Search for more papers by this author

  • This work was supported by the Deutsche Forschungsgemeinschaft (Project Bu 277/4) and the Fonds der Chemischen Industrie.

  • The designation 1,x dipole refers to the resonance structure of a compound in which the two charges are separated by the maximum distance, see 1,3 dipoles.

Abstract

original image

Azomethinimines and acetylenes react via [3+2]-cycloaddition to give a bicyclic, which on electrocyclic ring opening again affords an azomethinimine having a longer side chain. The reaction sequence can be repeated, permitting synthesis of 1,x dipoles.

Ancillary