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- Title
РЕАКЦИЯ АРОМАТИЧЕСКИХ КАРБОНОВЫХ КИСЛОТ С ФЕНИЛАЦЕТИЛЕНОМ В ПРИСУТСТВИИ КАТАЛИЗАТОРА.
- Authors
ПАРМАНОВ, А. Б.; НУРМАНОВ, С. Э.
- Abstract
Background. Vinyl esters of carboxylic acids are widely used in organic synthesis, in particular in acylation reactions, substrates in asymmetric hydrogenation, cycloaddition, aldol and Mannich reactions, and the synthesis of vinylarenes based on decarboxylation. Vinyl ethers are also used as monomers in polymerization reactions. Their preparation by the action of alkynes on carboxylic acids in the presence of 3d-metal catalysts is promising and requires additional study. Purpose. Synthesis of vinyl esters by the reaction of benzoic, 4-methylbenzoic, 4-bromobenzoic and 2-bromobenzoic acids with phenylacetylene under homogeneous conditions, in the presence of catalytic systems, studying the properties of the synthesis products, carrying out quantum chemical calculations of the process. Methodology. The interaction of substituted benzoic acids, in particular, 4-methylbenzoic acid, 4-bromobenzoic acid and 2-bromobenzoic acid with phenylacetylene, in the presence of catalysts, was used. The methods used were IR, ¹H, 13C NMR and mass spectral analysis. Originality. The synthesis of vinyl esters of benzoic, 4-methylbenzoic, 4-bromobenzoic and 2-bromobenzoic acids with tetrakis-(2-amino-5-ethylthio-1,3,4-thiadiazole) zinc(II) dinitrate ([Zn(C4H7S2)4](NO3)2) including phenylacetylene with the participation of a complex catalytic system. Findings. In the reaction of carboxylic acids with phenylacetylene, a mixture of combination products is formed according to the Markovnikov and Anti-Markovnikov rules. It has been established that the yield of vinyl esters increases in the series 4-CH3-C6H4COOH < C6H5COOH < 4-Br-C6H4COOH < 2-Br-C6H4COOH. The yield of the reaction products of phenylacetylene with carboxylic acids is: 44% (65/35) for 4-methylbenzoic acid, 67% (80/20) for benzoic acid, 78% (82/18) for 4-bromobenzoic acid, 82% (85 /15) for 2-bromobenzoic acid.
- Subjects
CHEMICAL processes; VINYL ethers; ESTERS; ETHYNYL benzene; BENZOATES; CARBOXYLIC acids; THIADIAZOLES; ACYLATION; RING formation (Chemistry)
- Publication
Uzbek Chemical Journal / O'Zbekiston Kimyo Jurnali, 2023, Issue 4, p17
- ISSN
0042-1707
- Publication type
Article