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  • Organic Chemistry  (688)
  • 1995-1999
  • 1980-1984
  • 1975-1979  (688)
  • 1977  (688)
  • 1
    Electronic Resource
    Electronic Resource
    Thalliumverbindungen als Katalysatoren für Umesterungen mit Glycidol und für Esteraustauschreaktionen mit Glycidylacetat (1977)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 60 (1977), S. 1845-1860 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Thallium compounds as catalysts for transesterifications and ester exchange reactionsThe transesterification of di-, tri- and tetracarboxylic alkyl esters with 2,3-epoxy-propanol was investigated in the presence of various metal compounds as catalysts. It was found that only thallium compounds catalyse the reactions under mild conditions without decomposition of 2,3-epoxypropanol. Many thallium compounds also proved to be very good catalysts for the reactions of 2,3-epoxypropanol with alkoxysilanes and the ester exchange reactions of di-, tri- and tetracarboxylic alkyl esters with 2,3-epoxypropyl-acetate.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19770600603
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  • 2
    Electronic Resource
    Electronic Resource
    Folgeprodukte halogenierter Aldehyde. XI [1]. Substitutionen am 2,5-Bis-trichlormethyl- und 2-Trichlormethyl-5-dichlormethylen-1,3-dioxolan-4-on-oxim (1977)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 319 (1977), S. 317-323 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Derivatives of Halogenated Aldehydes. XI. Substitution Reactions of 2,5-Bis-Trichloromethyl- and 2-Trichloromethyl-5-dichloromethylene-1,3-dioxolan-4-one Oxime2,5-Bis-trichloromethyl- (1) and 2-trichloromethyl-5-dichloromethylene-1,3-dioxolan-4-one oxime 2 are acylated with acyl halides, alkyl chlorocarbonates and N,N-dimethylcarbamyl chloride to give the corresponding O-acyl oximes 4-6, 9, 11 and 13. The addition of the oximes 1 and 2 to isocyanates yields the oxime carbamates 7 and 10, and the addition to N-acetyl-2,2,2-trichloroacetaldimine leads to the O-(1-acetamino-2,2,2-trichloroethyl) oximes 8 and 12. Oxime 2 forms a sodium salt 3 which gives the O-alkyl (15), the O-aryl (16) and the O-sulphonyl oximes (14) by reactions with alkyl halides or dialkyl sulfates, with activated aryl halides or with sulphonyl chlorides, respectively.
    Notes: 2,5-Bis-trichlormethyl- (1) und 2-Trichlormethyl-5-dichlormethylen-1,3-dioxolan-4-on-oxim 2 werden durch Acylieren mit Carbonsäurechloriden, Chlorkohlensäureestern und N,N-Dimethylcarbamoylchlorid in die entsprechenden O-Acyl-oxime 4-6, 9, 11 und 13 übergeführt. Durch Addition der Oxime 1 und 2 an Isocyanate entstehen die Oxim-carbamate 7 und 10 und durch Addition an N-Acetyl-2,2,2-trichloracetaldimin die O-(1-Acetamino-2,2,2-trichloräthyl)-oxime 8 und 12. Das Oxim 2 bildet ein Natriumsalz 3, das bei den Umsetzungen mit Alkylhalogeniden oder Dialkylsulfaten die O-Alkyl-oxime 15, mit aktivierten Arylhalogeniden die O-Aryl-oxime 16 und mit Sulfonsäurechloriden die O-Sulfonyl-oxime 14 ergibt.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19773190220
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  • 3
    Electronic Resource
    Electronic Resource
    Folgeprodukte halogenierter Aldehyde. XII [1]. O-Alkyl-O, O-bis-(1,2,2,2-tetrachloräthyl)- und O-Aryl-O, O-bis-(1,2,2,2-tetrachloräthyl)-phosphorsäureester (1977)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 319 (1977), S. 702-704 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Derivatives of Halogenated Aldehydes. XII. Alkyl-di(1,2,2,2-tetrachloroethyl) and Aryl-di(1,2,2,2-tetrachloroethyl) phosphates
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19773190424
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  • 4
    Electronic Resource
    Electronic Resource
    Folgeprodukte halogenierter Aldehyde IX. Die Synthese von Dialkyl-1,2,2,2-tetrachloräthyl- und Alkyl-phenyl-1,2,2,2-tetrachloräthyl-phosphaten (1977)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 319 (1977), S. 23-28 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Derivatives of Halogenated Aldehydes. IX. The Synthesis of Dialkyl-1,2,2,2-tetrachloroethyl- and Alkyl-phenyl-1,2,2,2-tetrachloroethyl PhosphatesDialkyl-1,2,2,2-tetrachloroethyl- (3a-t) and alkyl-phenyl-1,2,2,2-tetrachloroethyl phosphates 3u, v are prepared by reactions of 1,2,2,2-tetrachloroethyl phosphorodichloridate 1 with one mole of an alcohol or phenol to give alkyl(phenyl)-1,2,2,2-tetrachlorethyl phosphorochloridates 2a-k, followed by treatment of the latter with a second alcohol. The n.m.r. spectra of 2 and 3 are discussed.
    Notes: Dialkyl-1,2,2,2-tetrachloräthyl- (3a-t) und Alkyl-phenyl-1,2,2,2-tetrachloräthyl-phosphate 3u, v werden dargestellt durch Umsetzungen von 1,2,2,2-Tetrachloräthyl-dichlorphosphat 1 mit einem Mol eines Alkohols oder Phenol zu den Alkyl(Phenyl)-1,2,2,2-tetrachloräthyl-chlorphosphaten 2a-k und deren Reaktionen mit einem zweiten Alkohol. Die 1H-NMR-Spektren von 2 und 3 werden diskutiert.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19773190105
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesen von Heterocyclen, CCV. Reaktionen mit cyclischen Oxalylverbindungen, XX Reaktionen von 4-Benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dion mit aliphatischen Nitrilen (1977)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1977 (1977), S. 1751-1757 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses of Heterocyclic Compounds, CCV. - Reactions of Cyclic Oxalyl Compounds, XX. - Reactions of 4-Benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dione with Aliphatic NitrilesThe reaction of 4-benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dione (1) with butyro-. isobutyro-, and phenylacetonitrile under thermolysis conditions leads via the dibenzoylketene-intermediate 2 to the 2-alkyl-5-benzoyl-6-phenyl-1,3-oxazin-4-ones 3, which can be converted by hydrolysis into the N-acylacrylamides 4. 2-Benzoyl-3-phenyl-5,6-dihydro-1 H-pyrano[2,3-c]isoquinoline-1,6-dione (5) is formed as a by-product in the reaction of 1 and phenylacetolnitrile. The structure of 5 is confirmed by alkylation and oxidation reactions.
    Notes: 4-Benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dion (1) reagiert mit Butyro-, Isobutyro- und Phenylacetonitril unter Thermolysebedingungen über die Dibenzoylketen-Zwischenstufe 2 zu den 2-Alkyl-5-benzoyl-6-phenyl-1,3-oxazin-4-onen 3, die sich zu den N-Acylacrylsäureamiden 4 hydrolysieren lassen. Aus 1 und Phenylactonitril entsteht als Nebenprodukt 2-Benzoyl-3-phenyl-5,6-dihydro-1 H-pyrano[2,3-c]isochinolin-1,6-dion (5), dessen Struktur durch Alkylierung sowie Oxidation mit KMnO4 gesichert wurde.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197719771022
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  • 6
    Electronic Resource
    Electronic Resource
    Zur Bindungsisomerisierung von Acetylen- und Allen-Kohlenwasserstoffen. II [1]. Kinetische Untersuchungen über die Isomerisierung von Propin und Allen an einem sauren Molekularsiebkatalysator in der Gasphase (1977)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 319 (1977), S. 655-666 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: About the Bond Isomerization of Acetylenic and Allenic Hydrocarbons. II. Kinetic Studies on the Isomerization of Propine and Allene with an Acidic Molecular Sieve Catalyst in the Gas PhaseThe gas phase isomerization of propine and allene (propadiene) was studied on a molecular sieve 13X, modified with Ni and Ca, in the temperature range of 108-173 °C with the aid of a close circulation apparatus. The bond isomerization may be considered as an example of a monomolecular, reversible, heterogeneous catalyzed reaction of the type A ⇌ B. For the studied isomerizations the rate equations of the Langmuir-Hinshelwood-type were derived by kinetic analysis of the experimentally obtained dependence of the mole fractions from the residence time. The rate and adsorption constants of the Langmuir-Hinshelwood equations were determined, their physical interpretation was possible.
    Notes: Die Gasphasen-Isomerisierung des Propins und Allens (Propadiens) wurde an einem mit Ni und Ca modifizierten Molekularsieb vom Typ 13 X im Temperaturbereich von 108 bis 173 °C in einer Zirkulationsapparatur mit geschlossenem Kreislauf kinetisch verfolgt. Für die als Prototyp einer monomolekularen, reversiblen, heterogen katalysierten Reaktion vom Typ A ⇌ B anzusehende Bindungsisomerisierung wurden vollständige Geschwindigkeitsausdrücke vom Langmuir-Hinshelwood-Typ abgeleitet und durch kinetische Analyse der experimentell bestimmten Molenbruch-Kontaktzeit-Verläufe die Geschwindigkeits- und Adsorptionsgleichgewichtskonstanten ermittelt. Sämtliche Konstanten sind physikalisch interpretierbar.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19773190416
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  • 7
    Electronic Resource
    Electronic Resource
    Struktur von Cantharidin, C10H12O4 (1977)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 60 (1977), S. 740-742 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Structure of Cantharidine, C10H12O4An X-ray structure determination of the title compound confirms the correctness of the molecular stereochemistry as deduced earlier from chemical considerations.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19770600307
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  • 8
    Electronic Resource
    Electronic Resource
    Kristallin-flüssige 3,6-Diphenyl-1,2,4-triazine (1977)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 319 (1977), S. 475-484 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Liquid-crystalline 3,6-Diphenyl-1,2,4-triazinesThe synthesis of substituted 3,6-diphenyl-1,2,4-triazines is described and their liquid-crystalline properties are discussed. The melting characteristics of this homologous series is shown in tables and graphs.
    Notes: Die Synthesen mono- und disubstituierter 3,6-Diphenyl-1,2,4-triazine werden beschrieben und die kristallin-flüssigen Eigenschaften dieser Verbindungen diskutiert. Das Schmelzverhalten homologer Reihen wird in Abbildungen graphisch dargestellt.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19773190317
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  • 9
    Electronic Resource
    Electronic Resource
    Zur Stereochemie der aromatischen Claisen-Umlagerung. Thermische Umlagerung von erythroiden und threoiden ortho-Dienonen (1977)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 60 (1977), S. 2436-2459 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On the Stereochemistry of the Aromatic Claisen Rearrangement. Thermal Rearrangement of erythroid and threoid ortho-Dienones.Erythro- and threo-1-methyl-1-(1′-methyl-2′-propynyl)-2-oxo-1,2-dihydronaph-thalene (erythro- and threo-6) as well as erythro- and threo-2,6-dimethyl-6-(1′-methyl-2′-propynyl)-cyclohexa-2,4-dien-1-one (erythro- and threo-8) were obtained together with the corresponding aromatic ethers 5 and 7 by alkylation of 1-methyl-2-naphthol and 2,6-dimethyl-phenol, respectively in alcoholic potassium hydroxide solution with 1-methyl-2-propynyl p-toluenesulfonate (Scheme 2). The diastereoisomeric dienones 6 and 8 were easily separated by column chromatography on silica gel and its relative configuration at C(1) or C(6) and C(1′) deduced from the chemical shifts in their 1H-NMR.-spectra (Table 1). Hydrogenation of 6 and 8 using Lindlar catalyst yielded the corresponding erythro- and threo-configurated (1′-methyl-2′-propenyl)-dienones 10 and 13, respectively (Scheme 3) the thermal rearrangement of which were studied. The following results were obtained: threo-10 rearranged in benzene at 85-105° preferentially via a chair-like (C) transition state to yield 99,5% (E)- and 0,5% (Z)-(2′-butenyl) 1-methyl-2-naphthyl ether ((E)- and (Z)-14; ΔΔG105,7°≠ (C/B) = -4,0 kcal/mol). On the other hand, erythro-10 when heated at 105-125° in benzene gave 84,7% (E)- and 15,3% (Z)-14, i.e. in this case a boat-like (B) transition state is favoured (G105,7°≠ (C/B) = + 1,3 kcal/mol) (Scheme 5 and Table 2). The thermal rearrangement of dienones 13 led to the corresponding ethers 12 as well as p-allyl-phenols 11. Thus, heating of threo-13 at 20-42° in cyclohexane resulted in the formation of 2,5% of ether 12, consisting of 98% of the (E)- and 2% of the (Z)-isomer, and 97,5% of (E)-11 which contained, at a maximum, 0,5% of the (Z)-isomer, (Scheme 6 and Table 3). This means that both rearrangements occurred with a strong preference of the C transition state (G41,6°≠ (C/B, phenol) = -3,3 kcal/mol). On the contrary, erythro-13 when heated at 42-68° in cyclohexane yielded a 3:2 mixture of ether 12 and phenol 11 (Scheme 6). The ethereal part consisted of 88,0% of the (E)- and 12,0% of the (Z)-isomer which again shows that the B geometry predominated in the erythro transition state leading to the ether (G42,7°≠ (C/B)= + 1,3 kcal/mol). In the phenolic part 36-40% of the (E)-isomer and 64-60% of (Z)-isomer were found which means that in the para-Claisen rearrangement of erythro-13 the C arrangement is only slightly favoured (ΔΔG42,7°≠ (C/B)= -0,36 kcal/mol).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19770600731
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  • 10
    Electronic Resource
    Electronic Resource
    Experimente zum kompetitiven Einbau der Stereoisomeren des Farnesols in Cantharidin. 6. Mitteilung zur Biosynthese des Cantharidins5. Mitt.: siehe [1]. (1977)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 60 (1977), S. 2288-2294 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Experiments on the competitive incorporation of farnesol-stereoisomers into cantharidinFarnesol (2) has been demonstrated to be an efficient precursor for cantharidin (1), into which it is transformed by elimination of C(1), C(5), C(6), C(7) and C(7′) [1]. The following incorporation experiments with doubly labelled (3H and 14C) stereoisomers of farnesol present strong evidence that (E,E)- farnesol ((E,E)-2) in fact is the precursor for cantharidin, whereas (2E, 6Z)-2 and (Z,Z)-2 are not utilized for the biosynthesis of cantharidin. A possible mechanism for the incorporation of (2Z,6E)-farnesol ((2Z,6E)-2) to an extent of 56,8% relative to (E,E)-2 is discussed.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19770600719
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