Reaction of 2,5-diphenyl-1,2,3-diazaarsole with 2-diazopropane

Conclusions The reaction of 2-diazopropane with 2,5-diphenyl-1,2,3-diazaarsole (I) gave 2,4-di-phenyl-6,6-dimethyl-1-arsa-2,3-diazabicyclo[3.1.0]hex-3-ene (III).Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 230–231, January, 1986.The authors thank R. M. Mukhamadeeva and P. N. Sobolev for taking the spectra.     

Behavior of 1,1-diphenyl-2,5-dihydrophospholium salts toward bases: Ylide formation or ring opening

Efficient procedures are described leading to pure 3,4-R¹, R²-substituted 1,1-diphenyl-2,5-dihydrophospholium salts (R¹ = R² = CH₃, H; R¹ = CH₃, R² = H). Their behaviors toward bases such as nBuLi and tBuOK in THF or DMSO have been examined. According to the nature of the substituents R¹ and R², the complete monodeprotonation of these salts leads either to the corresponding pure five-membered cyclic ylide (and, in some cases, its prototropic isomer) or to a dienylphosphine resulting from a ring opening. The reactivity of the 3,4-dimethyl-disubstituted salt was especially studied. The corresponding monoylide functions as a good Wittig reagent, allowing stereoselective access to interesting alkadienylphosphine oxides and subsequently to trienes. However, in the presence of alkylating electrophiles, it reacts under an open dienylphosphine form giving rise to P-alkylated phosphonium salts. Nevertheless, this monoylide does not undergo further deprotonation into the corresponding cyclic diylide. Most of the synthetisized derivatives are original. © 1996 John Wiley & Sons, Inc.     

Molecular and crystal structure of 2,5-diphenyl-2-bora-1,3,5-dioxaphosphorinane

Conclusions In the crystal, 2,5-diphenyl-2-bora-1,3,5-dioxaphosphorinane has the sofa conformation with the axial orientation of the phenyl at the phosphorus atom and the dihedral angle of 36.8° between the C⁴O³B²O¹C⁶ and C⁴P⁵O⁶ planes.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2715–2718, December, 1986.     

Synthesis of 2-arylmethylidene-5-oxo-1,4-diphenyl-2,5-dihydro-1H-pyrazol-2-ium-3-olates

Condensation of several arylhydrazones with chlorocarbonyl phenyl ketene gave 2-(arylmethylidene)-5-oxo-1,4-diphenyl-2,5-dihydro-1H-pyrazol-2-ium-3-olates in high yields.     

Influence of medium acidity upon the luminescence properties of 2,5-diphenyl-1,3,4-oxadiazole and 2,5-diphenyl-1,3-oxazole

The luminescence properties of 2,5-diphenyl-1,3,4-oxadiazole and 2,5-diphenyl-1,3-oxazole in aqueous solutions of sulfuric acid (pH 7 to H_o − 10) were studied. The spectral parameters are essentially acidity dependent, which is due to the acid-base equilibria of these heterocycles both in the ground and in the first excited singlet states. The difference between these two compounds is governed by their dissimilar solvation. The basicity constants of 2,5-diphenyl-1,3,4-oxadiazole in the S₀ state (pK_BH+ = − 2.49) and 2,5-diphenyl-1,3-oxazole in the S₀ and S₁ states (pK_BH+ = −1.93, pK_BH+^* = 1.95) were experimentally obtained. The enthalpies of formation, electron charge density, and geometry of the bases and corresponding conjugate acids in the S₀ and S₁ states were calculated by the MNDO method.     

The synthesis and three-dimensional structure of 2,5-diphenyl-2-bora-1,3,5-dioxaphosphorinane

Conclusions Hydroxymethyldiphenylboryloxymethylphenylphosphine and 2,5-diphenyl-2-bora-1,3,5-di-oxaphosphorinane, in which the phenyl group at the phosphorus atom is predominantly found in the axial position, are formed in the reaction of di(hydroxymethyl)phenylphosphine with isobutyl diphenylborate.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2349–2352, October, 1979.     

A convenient synthesis of ethyl 3,3,3,-trifluoropropanoate and its 2-bromo derivative

Ethyl 3,3,3-trifluoropropanoate and ethyl 2-bromo-3,3,3-trifluoropropanoate have been synthesized. A common intermediate ethyl 3-chloro (or 3-bromo)-3,3-difluoropropanoate is involved in the two syntheses. These esters are obtained by oxidation of the corresponding acetals resulting from the radical addition of CF₂BrCl or CF₂Br₂ to ethyl vinyl ether.     

Synthesis and spectral-luminescence properties of hetarylethylene derivatives of 2,5-diphenyloxazole and 2,5-diphenyl-1,3,4-oxadiazole

A number of new organic luminophores was synthesized by PO olefination from 2- (4-bromomethylphenyl)-5-phenyloxazole and -1,3,4-oxadiazole and various heterocyclic aldehydes that contain a furan ring. The absorption and fluorescence spectra of the products in toluene, as well as their scintillation characteristics, were measured. The effect of the electronic nature of the substituents on the spectral-luminescence properties of the luminophores is discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 617–621, May, 1982.     

Conversion of 2, 5-diphenyl-1, 3,4-oxadiazole to 3, 5-diphenyl-4-aryl-1, 2, 4-triazoles

2, 5-Diphenyl-1, 3, 4-oxadiazoles are shown to react with aromatic amines on heating, to give 2, 5-diphenyl-4-aryl-1, 2, 4-triazoles.     

Conversion of 2, 5-diphenyl-1, 3,4-oxadiazole to 3, 5-diphenyl-4-aryl-1, 2, 4-triazoles

2, 5-Diphenyl-1, 3, 4-oxadiazoles are shown to react with aromatic amines on heating, to give 2, 5-diphenyl-4-aryl-1, 2, 4-triazoles.     

Thermochemical study of 2,5-dimethyl-3-furancarboxylic acid, 4,5-dimethyl-2-furaldehyde,and 3-acetyl-2,5-dimethylfuran

The standard (p° = 0.1 MPa) molar enthalpies of formation, in the gaseous state, at T = 298.15 K, for 2,5-dimethyl-3-furancarboxylic acid, 3-acetyl-2,5-dimethylfuran, and 4,5-dimethyl-2-furaldehyde were derived from the values of the standard molar enthalpies of formation, in the condensed phase, and the standard molar enthalpies of phase transition from the condensed to the gaseous state. The values of the standard molar enthalpies of formation of the compounds in the condensed phases were calculated from the measurements of the standard massic energies of combustion obtained by static bomb combustion calorimetry. The enthalpies of vaporization/sublimation were measured by Calvet high temperature microcalorimetry. For 2,5-dimethyl-3-furancarboxylic acid the standard enthalpy of sublimation was also calculated, by the application of the Clausius–Clapeyron equation, to the temperature dependence of the vapor pressures measured by the Knudsen effusion technique.     

19.

Bis(acetato)(4-benzyl-1,7-diphenyl-2,4,6-triazahepta-2,5-diene-κ2N2,N6)copper(II)     

S. W. Breuer  R. W. H. Small 《Acta Crystallographica. Section C, Structural Chemistry》1991,47(4):871-872

     

20.

Über die Umsetzung von 2-Methyl-2,5-diphenyl-imidazolin-4-thion und 2-Methyl-2,5-diphenyl-4-chlor-2H-imidazol mit aliphatischen und aromatischen Aminen,Alkoholen und Phenolen     

F. Asinger  D. Neuray  A. Saus  J. Gräber  U. Lames 《Monatshefte für Chemie / Chemical Monthly》1972,103(2):406-417

Zusammenfassung Aliphatische Amine bzw. Alkohole reagiren (in Gegenwart von PbO) mit 2-Methyl-2,5-diphenyl-imidazolin-4-thion (1) glatt zu 4-Alkylamino-2H-imidazolen (2 a-f, 7) bzw. 4-Alkoxy-2H-imidazolen (9 a-g). Die Darstellung von 4-Arylamino-2H-imidazolen (4 a-j) bzw. 4-Aroxy-2H-imidazolen (10 a-t) gelingt in guten Ausbeuten durch Umsetzung von 2-Methyl-2,5-diphenyl-4-chlor-2H-imidazol (3) mit aromatischen Aminen in siedenden Lösungsmitteln (Petroläther, Aceton) bzw. mit Phenolen in siedendem Aceton in Gegenwart von HCl-Acceptoren (K₂CO₃, Dabco). Die Umsetzung von3 mit Anthranilsäure liefert in 83proz. Ausbeute 1-Methyl-1,3-diphenyl-1H, 9H-imidazo[5,1-b]chinazolin-9-on (6). Aus3 und Thiophenol erhält man glatt 2-Methyl-2,5-diphenyl-4-phenylthio-2H-imidazol (11).

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On the reaction of 2-Methyl-2,5-diphenyl-imidazoline-4-thione and 2-Methyl-2,5-diphenyl-4-chloro-2H-imidazole with aliphatic and aromatic amines, alcohols and phenols (joint action of elemental sulfur and gaseous ammonia upon ketones, LXXVI

Aliphatic amines and alcohols (in the presence of PbO) easily react with 2-methyl-2.5-diphenyl-imidazoline-4-thione (1) to 4-alkylamino-2H-imidazoles (2 a-f, 7) and 4-alkoxy-2H-imidazoles (9 a-g), resp. 4-arylamino-2H-imidazoles (4 a-j) are prepared in good yields by the reaction of 2-methyl-2.5-diphenyl-4-chloro-2H-imidazole (3) with aromatic amines under reflux in light naphtha or acetone; in the same manner 4-aroxy-2H-imidazoles (10 a-t) are obtained from3 and phenols in boiling acetone in the presence of HCl-acceptors (K₂CO₃, Dabco). Reaction of3 with anthranilic acid leads to1-methyl-1.3-diphenyl-1H.9H-imidazo[5.1-b]chinazoline-9-one (6) in 83% yield. By reaction of thiophenol with3 2-methyl-2.5-diphenyl-4-phenylthio-2H-imidazole (11) is easily obtained.

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Herrn Prof. Dipl.-Ing., Dr. techn., Dr. e. h.Otto Kratky zum 70. Geburtstag herzlichst gewidmet.

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Teil der DiplomarbeitJ. Gräber, Techn. Hochschule Aachen, 1970.

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Teil der DiplomarbeitU. Lames, Techn. Hochschule Aachen, 1971.     

Über die Umsetzung von 2-Methyl-2,5-diphenyl-imidazolin-4-thion und 2-Methyl-2,5-diphenyl-4-chlor-2H-imidazol mit aliphatischen und aromatischen Aminen,Alkoholen und Phenolen

Zusammenfassung Aliphatische Amine bzw. Alkohole reagiren (in Gegenwart von PbO) mit 2-Methyl-2,5-diphenyl-imidazolin-4-thion (1) glatt zu 4-Alkylamino-2H-imidazolen (2 a-f, 7) bzw. 4-Alkoxy-2H-imidazolen (9 a-g). Die Darstellung von 4-Arylamino-2H-imidazolen (4 a-j) bzw. 4-Aroxy-2H-imidazolen (10 a-t) gelingt in guten Ausbeuten durch Umsetzung von 2-Methyl-2,5-diphenyl-4-chlor-2H-imidazol (3) mit aromatischen Aminen in siedenden Lösungsmitteln (Petroläther, Aceton) bzw. mit Phenolen in siedendem Aceton in Gegenwart von HCl-Acceptoren (K₂CO₃, Dabco). Die Umsetzung von3 mit Anthranilsäure liefert in 83proz. Ausbeute 1-Methyl-1,3-diphenyl-1H, 9H-imidazo[5,1-b]chinazolin-9-on (6). Aus3 und Thiophenol erhält man glatt 2-Methyl-2,5-diphenyl-4-phenylthio-2H-imidazol (11).

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On the reaction of 2-Methyl-2,5-diphenyl-imidazoline-4-thione and 2-Methyl-2,5-diphenyl-4-chloro-2H-imidazole with aliphatic and aromatic amines, alcohols and phenols (joint action of elemental sulfur and gaseous ammonia upon ketones, LXXVI

Aliphatic amines and alcohols (in the presence of PbO) easily react with 2-methyl-2.5-diphenyl-imidazoline-4-thione (1) to 4-alkylamino-2H-imidazoles (2 a-f, 7) and 4-alkoxy-2H-imidazoles (9 a-g), resp. 4-arylamino-2H-imidazoles (4 a-j) are prepared in good yields by the reaction of 2-methyl-2.5-diphenyl-4-chloro-2H-imidazole (3) with aromatic amines under reflux in light naphtha or acetone; in the same manner 4-aroxy-2H-imidazoles (10 a-t) are obtained from3 and phenols in boiling acetone in the presence of HCl-acceptors (K₂CO₃, Dabco). Reaction of3 with anthranilic acid leads to1-methyl-1.3-diphenyl-1H.9H-imidazo[5.1-b]chinazoline-9-one (6) in 83% yield. By reaction of thiophenol with3 2-methyl-2.5-diphenyl-4-phenylthio-2H-imidazole (11) is easily obtained.

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Herrn Prof. Dipl.-Ing., Dr. techn., Dr. e. h.Otto Kratky zum 70. Geburtstag herzlichst gewidmet.

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Teil der DiplomarbeitJ. Gräber, Techn. Hochschule Aachen, 1970.

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Teil der DiplomarbeitU. Lames, Techn. Hochschule Aachen, 1971.