Summary
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1.
ω-Diacetylenic esters were prepared by the condensation of ω-haloalkanoic esters with the monosodium derivative of butadiyne in liquid ammonia. In this way, from 4-pentynyl 9-chlorononanoate and 4-chlorobutyl 11-chloroundecanoate, 4-pentynyl 10,12-tridecadiynoate and 5,7-octadiynyl 12,14-pentadecadiynoate, respectively, were obtained.
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2.
By the oxidative condensation of these esters under conditions of high dilution a 19-membered triacetylenic lactone and a 24-membered tetraacetylenic lactone were obtained, and these were converted into the corresponding tri- and tetra-enic macrocyclic lactones by hydrogenation.
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Bergel'son, L.D., Molotkovskii, Y.G. Unsaturated acids and macrocyclic lactones communication 6. Tri- and tetra-acetylenic macrocyclic lactones and the corresponding polyenes. Russ Chem Bull 12, 94–98 (1963). https://doi.org/10.1007/BF00846956
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DOI: https://doi.org/10.1007/BF00846956