SYNTHESIS OF ACETYLENE ALCOHOLS BASED ON THE ETHINYLATION OF SOME HETEROATOMIC ALDEHYDES WITH THE PARTICIPATION OF VARIOUS CATALYSTS
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Аннотация:
In this research work, the catalytic systems InBr3/Et3N/Et2O and ProPhenol/Me2Zn/TGF were used for the first time, based on the reactions of enantioselective ethinylation of acetylene, phenylacetylene with some aldehydes - thiophene-2-carbaldehyde, 3-methylthiophene-2-carbaldehyde, furan-2- carbaldehyde, pyridine-3-carbaldehyde, quinoline-2-carbaldehyde and 3-bromo-4-pyridinecarbaldehyde, the synthesis reactions of the corresponding acetylene alcohols were studied. The influence of the used complex systems on the efficiency of the formation of acetylene alcohols is proposed. and reaction mechanisms are presented. A number of factors influencing the yield of the product were studied - temperature, reaction duration, influence of the amount of catalyst and solvents, substrate and reagents. Based on the results obtained, the most alternative conditions for the processes were found. The composition, purity, structure and quantum chemical properties of the synthesized acetylene alcohols were confirmed by modern physicochemical methods - IR, 1H-NMR, 13C-NMR spectroscopy, mass spectrometry, chromatography. A number of production efficiencies of synthesized acetylene alcohols have been determined. In the process, a number of propensities for the nucleophilic addition reaction were determined in accordance with the nature of the substituents retained by the heteroatomic element in the aldehyde molecule, their spatial arrangement and nature of action.
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