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

Анотація

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 ∆δ^R/S, while proton signals of the less bulky group are shifted to a weaker field with a negative value of ∆δ^R/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 Δδ^R/S data in the NMR ¹H spectra during such interaction it was found that they converted  to diastereomers.