SYNTHESIS OF AROMATIC ACETYLENE ALCOHOLS USING COMPLEX CATALYTIC SYSTEMS

Abstract

Some cyclic ketones (cyclopentanone, cyclohexanone, 2-methylcyclohexanone, menthol, camphor and adamantanone) enantioselective alkynylation reactions with phenylacetylene have been studied in the presence of complex catalytic systems - Zn(OTf)2/NЕt3/MeCN, 3,3′-Ph2BINOL-2Li/TGF and BuLi/KOtBu/TGF. Synthesis were performed new aromatic acetylene alcohols – 1-(2-phenylathinyl) cyclopentanol (1), 1-(2-phenylethinyl)cyclohexanol (2), 2-methyl-1-(2-phenylethinyl)cyclohexanol (3), 2-isopropyl-5-methyl-1-(2-phenylethinyl)cyclohexanol (4), 1,7,7,-trimethyl-2-(2-phenylethinyl)bicyclo [2.2.1] heptanol-2 (5) and 2-phenylethinyltricyclo [3,3,1.03,7]nonanol-2 (6). Synthesis reactions of aromatic acetylene alcohols, activation energies were determined, kinetics of chemical changes were analyzed, reaction mechanisms were proposed. The course of the reactions and the effect of the selected ketone molecule size, structure and number of rings on the product yield were analyzed. A series of catalytic activity of the applied complex catalytic systems has been developed.