89232-08-6Relevant articles and documents
Site-specific 2H-labeled oleic acid and derived esters for use as tracers of ethyl oleate metabolism in honey bees
Chen, Hao,Plettner, Erika
experimental part, p. 66 - 70 (2012/06/30)
The inventory of labeled fatty acids and protocols for their syntheses are constantly increasing, but site-specific labeled precursors in biosynthetic studies are still needed. Ethyl oleate (EO) is an important primer pheromone in honeybees, which is responsible for the regulation of behavioral maturation. During our biosynthetic studies on EO, a site-specific labeled oleic acid precursor was required. In this report, a synthetic route adaptable to the preparation of [9,10,11,11-D4] oleic acid and its derived esters for use as tracers of EO metabolism in honey bees is presented. Copyright
Photochemistry of Alkyl Halides. 11. Competing Reaction via Carbene and Carbocationic Intermediates
Kropp, Paul J.,Sawyer, Joy A.,Snyder, John J.
, p. 1583 - 1589 (2007/10/02)
Isotopic analysis of the unsaturated products 6 and 15 resulting from irradiation of the labeled iodides 1-1,1-d2, 1-2,2-d2, and 13-1-d has revealed that they are formed substantially, but not exclusively, via α elimination.The unsaturated products thus arise via competing pathways involving carbene intermediates as well as the previously recognized radical and carbocationic intermediates.Irradiation of iodide 22 in methanol-d afforded ether 23 with partial incorporation of deuterium, but the accompanying ether 24 was formed with no detectable incorporation.Thus, ether 23 is formed via competing pathways involving the carbene 28 and the carbocation 25, whereas ether 24 is formed exclusively via the carbocationic pathway.A mechanism involving formation of the carbene intermediates via either α-hydrogen atom or α-proton transfer within the previously proposed intervening radical and ion pairs is suggested.One iodide studied, 17-2-d, exhibited no detectable α elimination.
