120569-51-9Relevant articles and documents
Synthesis of 1,3-Diynes via Cadiot-Chodkiewicz Coupling of Volatile, in Situ Generated Bromoalkynes
Knutson, Phil C.,Fredericks, Haleigh E.,Ferreira, Eric M.
supporting information, p. 6845 - 6849 (2018/10/25)
A convenient Cadiot-Chodkiewicz protocol that facilitates the use of low molecular weight alkyne coupling partners is described. The method entails an in situ elimination from a dibromoolefin precursor and immediate subjection to copper-catalyzed conditions, circumventing the hazards of volatile brominated alkynes. The scope of this method is described, and the internal 1,3-diyne products are preliminarily evaluated in ruthenium-catalyzed azide-alkyne cycloadditions.
Synthesis of 7E,9Z-dodecadienyl acetate, the sex pheromone of Lobesia botrana Shiff
Chrelashvili, Z. G.,Mavrov, M. V.,Dolidze, A. V.,Voronkov, A. P.,Serebryakov, E. P.
, p. 734 - 736 (2007/10/02)
Two syntheses of 7E,9Z-dodecadienyl acetate from 1,3-butadiyne were carried out using either 2E,4Z-heptadienyl acetate or 1-bromo-3E,5Z-octadiene as the key intermediates.The latter underwent organocopper cross-coupling with the respective complementary Grignard reagents (prepared from the corresponding 1-tert-butoxy-ω-chlorohydrins) as alkylating agents.
