Exchange reaction between epoxides and chlorohydrins

Conclusions We determined the equilibrium constant of the exchange reaction between epichlorohydrin and 1-chloro-2-hydroxy-3-phenoxypropane, which leads to the formation of phenyl glycidyl ether and glycerol 1,3-dichlorohydrin.Translated from Izvestiya Akademii Nauk SSR, Seriya Khimicheskaya, No. 2, pp. 450–451, February, 1979.     

Mechanism of reaction of phenyl glycidyl ether with phenyl benzoate in the presence of water

The reaction of phenyl glycidyl ether with phenyl benzoate in the presence of water was investigated by adsorption liquid chromatography.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 131–133, January, 1990.     

Reaction of phenylbenzoxazole with phenyl glycidyl ether

Conclusions The reaction of phenyibenzoxazole with phenyl glycidyl ether is not limited to the addition of the -oxide ring to the C=N bond of phenyibenzoxazole, but is followed by addition of a second molecule of phenyl glycidyl ether with the formation of an N derivative of hydroxyaniline.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1356–1359, June, 1987.     

Kinetic and Quantum-Chemical Study of Oxirane Ring Cleavage with Acids

Kinetic and thermodynamic parameters of the reactions of phenyl glycidyl ether and epichlorohydrin with bis(alkylpolyethylene glycol) ether of orthophosphorus acid (oxyphos KD-6) are established. It is shown that the difference in the reactivity of the oxiranes is caused by the electronic effects of substituents and the protonation by the phenolic oxygen atom of phenyl glycidyl ether. Basic solvents decrease the reactivity of the systems. Based on AM1 semiempirical quantum-chemical calculations, a hydroxycarbocation mechanism of the oxirane ring opening was proposed, involving initial formation of unstable cis- and trans-oxonium structures.     

Spatial structure of phosphorus-containing heterocycles

Conclusions An investigation of the PMR spectra over a wide temperature range in different solvents, the dipole moments, and the Kerr constants of 2-dialkylamino-1,3,2-dioxaphosphepanes with a planar group of atoms in the heterocycle (benzene ring, multiple bond) has demonstrated the existence of a conformational equilibrium between the chair form with equatorial position of the dialkylamino group and the twist form.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 588–593, March, 1982.     

Investigation of the influence of intramolecular electrostatic interactions on the conformational equilibrium in pyrimidine nucleosides by the PMR method

The influence of solvents on the PMR spectra of uridine and cytidine has been studied. Because of intramolecular electrostatic interactions (IEIs) between the 2-keto oxygen and the freely rotating 2-hydroxyl, the position of the conformational equilibrium in the pyrimidine nucleosides but not in purine and deoxy nucleosides, depends substantially on the dielectric constant of the solvent and the size of the partial negative charge on the 2-keto oxygen of the base. It has been shown that an increase in the IEI leads to an increase in the 3-endo (N) population of the ribose ring and to an increased influence of the temperature on the state of the conformational equilibrium.All-Union Scientific-Research Institute of Applied Biochemistry, Olaine. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 362–366, May–June, 1981.     

Reaction of phenyl glycidyl ether with triphenyl isocyanurate

Conclusions On the example of the reaction of triphenyl isocyanurate with phenyl glycidyl ether it was shown that oxirane rings when heated can react with the isocyanurate ring to give oxazolidone fragments.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1645–1646, July, 1981.     

Reaction of phenyl glycidyl ether with N-trimethylsilylaniline and trimethylsiloxybenzene

Conclusions It was shown by the IR spectroscopy method that the reaction of phenyl glycidyl ether with trimethylsiloxybenzene and N-trimethylsilylaniline proceeds via insertion of the opened epoxide ring between the Si-O and Si-N atoms.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 454–458, February, 1978.     

Reaction of diphenylcarbodiimide with phenyl glycidyl ether

Conclusions The reaction of diphenylcarbodiimide with phenyl glycidyl ether gives 3-phenyl-5-phenoxymethyl-2-N-phenyliminooxazolidine, which, in contrast to a number of substituted iminooxazolidines, does not isomerize to the corresponding imidazolidinone when heated to 250°.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 474–476, February, 1983.     

Reactions that occur during the synthesis of 3-phenyl-5-phenoxymethyl-2-N-phenyliminooxazolidine

Conclusions 3-Phenyl-5-phenoxymethyl-2-N-phenyliminooxazolidine, formed by the reaction of diphenyl-carbodiimide with phenyl glycidyl ether, reacts with an excess of the latter to give 3-phenyl-5-phenoxymethyl-2-oxazolidone.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2152–2153, September, 1983.     

Reaction rate of α-oxides with aliphatic amines

Conclusions Butylamine reacts with phenyl glycidyl ether by a mechanism that can be depicted as two processes that proceed in parallel, with a first and second order of reaction in amine. The ratio between the reaction routes depends on the temperature.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2828–2829, December, 1977.     

Reactions of 2-aminobenzothiazoles with phenyl glycidyl ether

In acidic media 2-aminobenzothiazole and its derivatives react with phenyl glycidyl ether at the ring nitrogen atom, while in alkaline media they react at the exocyclic nitrogen atom. The structures of the compounds were proved by spectral methods and alternative synthesis.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 685–691, May, 1991.     

Kinetics of Photocationically Curable Formulations Involving Glycerol Diglycidyl Ether and Phenyl Glycidyl Ether

Kinetic analysis of formulations based on glycerol diglycidyl ether and phenyl glycidyl ether were carried out in the presence of sulfonium salt as initiator at 35 mW cm^?2using photo differential scanning calorimeter and the final conversion was found to increase with an increase in phenyl glycidyl ether content. The effects of formulation monomer ratios at three different temperatures were studied. The variations in the observed kinetic parameters can be related to increase in mobility of reactive species with temperature, distance of counter ion from the propagating cationic center, as well as extent of crosslinking reaction which controlled the course and duration of the reaction. The applicability of autocatalytic kinetic model was also evaluated and the system underwent early gelation and the activation energy decreased with an increase in phenyl glycidyl ether content. Analysis of stable photocured films containing glycerol diglycidyl ether and phenyl glycidyl ether showed better thermal stability than rigid films obtained with glycerol diglycidyl ether.     

Thermokinetics of the reaction of phenyl glycidyl ether with aniline

The thermokinetic curves in the reaction of phenyl glycidyl ether with aniline were calculated for various compositions of the reaction mixture and temperatures. In addition to the main exothermic effect related to the epoxide ring opening, another exothermic effect of unknown nature was observed. The kinetic data obtained are explained in terms of structural changes caused by the self-aggregation of the reaction product molecules. The “kinetic investigation” approach provides a quantitative analysis of calorimetric data.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 371–375, February, 2005     

Study of chemical processes in the modification of epoxide polymers by aluminum oxide

The processes occurring during the modification of epoxy polymers by various polymorphic aluminum oxide modifications (γ-AlO(OH), γ-Al₂O₃, α-Al₂O₃) with epoxy groups were studied by the methods of IR Fourier spectroscopy, chemical analysis, and differential scanning calorimetry (DSC) by an example of a model compound (phenyl glycidyl ether). Two types of interactions were revealed: a direct chemical reaction of phenyl glycidyl ether with the surface hydroxy groups of alyminum oxide, and phenyl glycidyl ether homopolymerization. By processing by graphical method the data of chemical analysis on the diminishing in amount of epoxy groups in the course of the polycondensation reaction the value of activation energy 106–110 kJ mol⁻¹ of the process of phenyl glycidyl ether interaction with aluminum γ-oxide was determined.     

Structure and ring-chain tautomerism of 2-hydroxy-5-methyl-3,4-benzocinnamaldehyde

The previously undescribed 2-hydroxy-5-methyl-3,4-benzocinnamaldehyde was synthesized. A cyclic 2-hydroxy-2H-chromene structure in the crystalline state and in nonpolar solvents was established for it by IR, UV, and PMR spectroscopy. It is shown that transition to a polar solvent leads to the establishment of a tautomeric ring-chain equilibrium, the position of which is determined by the type of solvent.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 610–613, May, 1982.     

PMR study of the conformational behavior of 2,5,5-trisubstituted 1,3,2-dioxaborinanes

The conformational behavior of 2,5,5-trisubstituted 1,3,2-dioxaborinanes was studied by PMR spectroscopy. Molecules with similar substituants at C(₅) are in a state of rapid ring inversion between two energetically equivalent forms. In the case of different substituents, the inversion proceeds between energetically inequivalent states with a shift in the equilibrium toward one of them.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 558–561, April, 1986.     

Interactions Intramoleculaires—X: Etude par RMN des Équilibres Conformationnels de Cyclohexènes Monosubstitutés en 4 et du Dicyano-1,2 Cyclohexane trans

The conformational free energies of CN, Cl and COOC₂H₅ substituents have been evaluated from the PMR spectra of 4-substituted 3,3,6,6-d₄-cyclohexene. The PMR spectra of trans-1,2-dicyano-3,3,6,6-d₄-cyclohexane permit the conformational equilibrium (in different solvents) and the gauche diequatorial interaction energy between the two CN substituents to be estimated.