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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.