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SM ISO690:2012 ROŞCA, Gheorghe, PATRAŞCU, Teodor, ODOBESCU, Vasilisa, POPUŞOI, Oleg. Sinteza aldehidelor cis-9-tetradecenal şi cis-11-hexadecenal – componenţi ai feromonului sexual al moliei florii-soarelui Homoeosoma Nebulella Hbn. In: Protecţia plantelor - realizări şi perspective, Ed. 47, 27-28 octombrie 2015, Кишинев. Кишинев: "Print-Caro" SRL, 2015, nr.47, pp. 263-265. ISBN 978-9975-56-266-9 . |
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Protecţia plantelor - realizări şi perspective nr.47, 2015 |
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Simpozionul "Protecţia plantelor - realizări şi perspective" 47, Кишинев, Moldova, 27-28 octombrie 2015 | ||||||
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Pag. 263-265 | ||||||
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The aldehydes cis-9-tetradecenyl aldehyde and cis-11-hexadecenyl aldehyde – the components of sunflower moth sex pheromone were synthesized from the alkyl-derivatives of the propargilic alcohol through their isomerization in the presence of sodium amide in ethylenediamine to the adequate acetylenic alcohols with a terminal triple bond. Hydroxyl group protection of the alcohols obtained with 2,3-dihydropyran, followed by alkylation with 1-bromo-heptane bromide in liquid ammonia, leads to acetales 1-(2׳-tetrahydropyranyloxy)-tetradecine-9 [1-(2׳-tetrahydropyranyloxy)- hexadecyne-11], which, after hydroxyl group deprotecting (16% sulfuric acid, ethanol), are transformed in acetylenic alcohol tetradecyne-9-ol-1 [hexadecine-11-ol-1]. The las is reduced in the presence of a catalyst of Ni with ethylenediamine in ethanol. And then is transformed in cis-9- tetradecenol-1 [respective cis-11-hexadecenol-1]. Through oxidation the alcohols thus obtained with chromatepyridine in methylenechloride the aldehydes cis-9- tetra--decenyl aldehide [respective cis-11-hexadecenyl aldehide] are obtained — components of sun-flower moth sex pheromone. |
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Cuvinte-cheie synthesis, sex pheromone, european sunflower moth, protection, reduction, oxidation |
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