Vicinal Dilithioalkenes by Addition of Lithium to Simple Cyclic and Acyclic Alkynes

Authors

  • Prof. Dr. Adalbert Maercker,

    Corresponding author
    1. Institut für Organische Chemie der Universität, Adolf-Reichwein-Strasse, D-5900 Siegen (FRG)
    • Institut für Organische Chemie der Universität, Adolf-Reichwein-Strasse, D-5900 Siegen (FRG)
    Search for more papers by this author
  • Dipl.-Chem. Thomas Graule,

    1. Institut für Organische Chemie der Universität, Adolf-Reichwein-Strasse, D-5900 Siegen (FRG)
    Search for more papers by this author
  • Ulrich Girreser

    1. Institut für Organische Chemie der Universität, Adolf-Reichwein-Strasse, D-5900 Siegen (FRG)
    Search for more papers by this author

  • Polylithium Organic Compounds, Part 5. This work was supported by the Fonds der Chemischen Industrie.—Part 4: [1].

  • Dedicated to Professor Hans Jürgen Bestmann on the occasion of his 60th birthday

Abstract

original image

The use of 1,2-dilithio(cyclo)alkenes on a preparative scale in organic synthesis is made possible by the title reaction. The addition of lithium to cyclooctyne in ether (− 35°C, 2h) results in the formation of a yellow solution of cis-1,2-dilithiocyclooctene. Acyclic alkenes react much more slowly with lithium (20°C, 48 h) to give trans-dilithioalkenes, which are insoluble in ether.

Ancillary