СИНТЕЗ І ВИЗНАЧЕННЯ АБСОЛЮТНОЇ КОНФІГУРАЦІЇ МОНОЕСТЕРІВ α –ГЛІКОЛЕЙ АЛЛІЛОВОГО ТА ПРОПАРГІЛОВОГО СПИРТІВ МЕТОДОМ ПМР СПЕКТРОСКОПІЇ

• Datum: 2020
• Hauptverfasser: Talybov, Gulahmad, Baghirli, Aygun, Shirinova, Najiba
• Format: Artikel
• Sprache: English
• Veröffentlicht: V.I.Vernadsky Institute of General and Inorganic Chemistry 2020
• Online Zugang: https://ucj.org.ua/index.php/journal/article/view/149
• Назва журналу: Ukrainian Chemistry Journal

The synthesis of previously unknown unsaturated aromatic oxyethers was carried out by reaction of chloromethylpropargyl(allyl) ether with phenacyl bromide, with the participation of the chiral catalyst - (+)-benzotetramisole, and their configurations were also established. It was shown the anisotropic effect of the phenyl group in the acid chloride of α-methoxytrifluoromethylphenylacetic acid (MTPA-Cl) on the halogenaryl group. Such effect leads to screening of the latter, and this, in turn, leads to a shift to a strong field and positive values of ∆δR/S, while proton signals of the less bulky group are shifted to a weaker field with a negative value of ∆δR/S. The interaction of chloromethylpropargyl (allyl) ether with phenacylbromide with the participation of the chiral catalyst - (+) - benzotetramisole leads to aromatic allyl and propargyl alcohol monoethers. By the chiral derivative agent (CDA) chloride anhydride- α-trifluoro-methyl-phenyl-acetic acid (MTPA-Cl) the absolute configuration of compounds was determined. Due to comparing the ΔδR/S data in the NMR 1H spectra during such interaction it was found that they converted  to diastereomers.