Polylithium Organic Compounds, Part 5. This work was supported by the Fonds der Chemischen Industrie.—Part 4: .
Article first published online: 22 DEC 2003
Copyright © 1986 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 25, Issue 2, pages 167–168, February 1986
How to Cite
Maercker, A., Graule, T. and Girreser, U. (1986), Vicinal Dilithioalkenes by Addition of Lithium to Simple Cyclic and Acyclic Alkynes. Angew. Chem. Int. Ed. Engl., 25: 167–168. doi: 10.1002/anie.198601671
Dedicated to Professor Hans Jürgen Bestmann on the occasion of his 60th birthday
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 19 AUG 1985
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.