Penta-1,3-diyne reacts with n-butyl-lithium in the presence of NNN′N′-tetramethylethylenediamine to give C5Li4 which upon treatment with water yields a mixture of penta-1,3-diyne, penta-1,4-diyne, and penta-1,2-dien-4-yne.
R. West and T. L. Chwang, J. Chem. Soc. D, 1971, 813 DOI: 10.1039/C29710000813
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