Author
V. G. Glukhovtsev
Bio: V. G. Glukhovtsev is an academic researcher from Russian Academy of Sciences. The author has contributed to research in topics: Furan & Tetrahydrofuran. The author has an hindex of 1, co-authored 41 publications receiving 9 citations.
Topics: Furan, Tetrahydrofuran, Cyclopropane, Ketone, Ring (chemistry)
Papers
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TL;DR: The liquid phase oxidation of tetrahydrofuran and 2-methyltetrahydron-fragments with oxygen, in the presence of UV light, gave the hydroperoxides in respective concentrations of 20 and 60% as mentioned in this paper.
Abstract: 1.
The liquid-phase oxidation of tetrahydrofuran and 2-methyltetrahydrofuran with oxygen, in the presence of UV light, gave the hydroperoxides in respective concentrations of 20 and 60%.
2.
The formed 2-methyltetrahydrofuran hydroperoxide is composed of two isomers: 2-methyl-2-peroxytetrahydrofuran and 2-methyl-5-peroxytetrahydrofuran.
2 citations
TL;DR: According to the data of the IR spectra, the 4-hydroxy ketones exist in both the open and cyclic (hemiacetal) forms as discussed by the authors, the amount of the open form increases with increase in the steric hindrance in the cyclization step.
Abstract: 1.
Some 4- and 5-hydroxyketones were synthesized by the free-radical addition of alcohols toα,β-unsaturated ketones.
2.
According to the data of the IR spectra, the 4-hydroxyketones exist in both the open and cyclic (hemiacetal) forms. The amount of the open form increases with increase in the steric hindrance in the cyclization step. The 5-hydroxyketones exist only in the open form.
1 citations
TL;DR: By reductive amination these ketones and aldehydes were converted into the corresponding furan amines as mentioned in this paper, and by vapor phase hydrogenation over platinized asbestos at 250° α,γ,γγ,5-tetramethyl-2-furanpropylamine was converted into 2-butyl-3,3,5trimethylpyrrolidine.
Abstract: 1.
By the reactions of 2-methylfuran with acrolein, crotonaldehyde, and mesityl oxide furan aldehydes and ketones were synthesized, and by reductive amination these ketones and aldehydes were converted into the corresponding furan amines.
2.
By vapor-phase hydrogenation over platinized asbestos at 250° α,γ,γ,5-tetramethyl-2-furanpropylamine was converted into 2-butyl-3,3,5-trimethylpyrrolidine.
1 citations
TL;DR: In this paper, the vinyl ethers of methyl- and dimethylcyclopropylcarbinol were synthesized, due to high steric hindrance, and also the hydrogenation of its vinyl ether were much slower than in the case of methylcycloprithmic carbinol.
Abstract: 1.
The vinyl ethers of methyl- and dimethylcyclopropylcarbinol were synthesized.
2.
Due to high steric hindrance, the vinylation of dimethylcyclopropylcarbinol and also the hydrogenation of its vinyl ether were much slower than in the case of methylcyclopropylcarbinol.
1 citations
TL;DR: In this paper, the thermal decomposition of 2-methyltetrahydrofuran in solution was studied and the principal products were identified, and it was shown that the decomposition proceeds to a large degree with an opening of the tetrahedron ring.
Abstract: A study was made of the thermal decomposition of the hydroperoxide and peroxide of 2-methyltetrahydrofuran in solution, the principal products were identified, and it was shown that the decomposition proceeds to a large degree with an opening of the tetrahydrofuran ring A reaction mechanism was proposed
1 citations
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TL;DR: In this article, the data dealing with reductive amination of oxygen-containing organic compounds of different classes are systematised and new data on the amination agents and the catalysts used are presented.
Abstract: The data dealing with reductive amination of oxygen-containing organic compounds of different classes are systematised. New data on the amination agents and the catalysts used are presented. The dependence of the reactivity of reagents on their structures is considered. The bibliography includes 249 references.
83 citations
TL;DR: It is found that the hydroperoxide complex is stabilized by ∼4 kJ/mol (Gibbs free energy) more than the alcohol complex, a result that is backed by a number of calculated parameters and can be explained by a weaker OH bond in the Hydroperoxide.
Abstract: Hydroperoxides are formed in significant amounts in the atmosphere by oxidation of volatile organic compounds and are key in aerosol formation. In a room-temperature experiment, we detected the formation of bimolecular complexes of tert-butyl hydroperoxide (t-BuOOH) and the corresponding alcohol tert-butanol (t-BuOH), with dimethyl ether (DME) as the hydrogen-bond acceptor. Using a combination of Fourier-transform infrared spectroscopy and quantum chemical calculations, we compare the strength of the OH–O hydrogen bond and the total strength of complexation. We find that, both in terms of observed red shifts and determined equilibrium constants, t-BuOOH is a significantly better hydrogen-bond donor than t-BuOH, a result that is backed by a number of calculated parameters and can be explained by a weaker OH bond in the hydroperoxide. On the basis of combined experimental and theoretical results, we find that the hydroperoxide complex is stabilized by ∼4 kJ/mol (Gibbs free energy) more than the alcohol comp...
23 citations
TL;DR: This study compares the whole-cell biocatalytic route with the enzymatic route to enantiopure (S)-2 and investigates factors determining performance and outcome of the bioreductions.
Abstract: Biocatalytical approaches have been investigated in order to improve accessibility of the bifunctional chiral building block (5S)-hydroxy-2-hexanone ((S)-2). As a result, a new synthetic route starting from 2,5-hexanedione (1) was developed for (S)-2, which is produced with high enantioselectivity (ee >99%). Since (S)-2 can be reduced further to furnish (2S,5S)-hexanediol ((2S,5S)-3), chemoselectivity is a major issue. Among the tested biocatalysts the whole-cell system S. cerevisiae L13 surpasses the bacterial dehydrogenase ADH-T in terms of chemoselectivity. The use of whole-cells of S. cerevisiae L13 affords (S)-2 from prochiral 1 with 85% yield, which is 21% more than the value obtained with ADH-T. This is due to the different reaction rates of monoreduction (1→2) and consecutive reduction (2→3) of the respective biocatalysts. In order to optimise the performance of the whole-cell-bioreduction 1→2 with S. cerevisiae, the system was studied in detail, revealing interactions between cell-physiology and xenobiotic substrate and by-products, respectively. This study compares the whole-cell biocatalytic route with the enzymatic route to enantiopure (S)-2 and investigates factors determining performance and outcome of the bioreductions.
23 citations
TL;DR: In spite of a large number of publications describing the preparation of fluorinated furan derivatives, there is no systematized overview of the methods of their synthesis as mentioned in this paper, so we refer the reader to the survey of the main schemes of syntheses of fluorofurans and perfluoroalkylfurans.
18 citations
TL;DR: An efficient palladium-catalyzed aerobic alkenylhydroxylation cyclization of allenamide derivatives to synthesize piperidinol derivatives with excellent regioselectivity was developed as discussed by the authors.
Abstract: An efficient palladium-catalyzed aerobic alkenylhydroxylation cyclization of allenamide derivatives to synthesize piperidinol derivatives with excellent regioselectivity was developed. Both AgF and THF were proved to be important in the activation of molecular oxygen during this transformation. DFT calculation provided an explanation for the obtained E and Z configurations of the formed double bond, which might be the steric hindrance between two groups on C1 and C7. Mechanistic studies indicated that the reaction might undergo a radical process and a tentative catalytic cycle was proposed.
9 citations