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  • 1
    Electronic Resource
    Electronic Resource
    Fluorierungsreaktionen an 3,4-Dichlor-1,2,5-thiadiazol (1982)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 115 (1982), S. 2135-2140 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Fluorination Reactions at 3,4-Dichloro-1,2,5-thiadiazoleFrom the title compound 1 and KF in sulfolane 3-chloro-4-fluoro- (2) and 3,4-difluoro-1,2,5-thiadiazole (3) are obtained. In the reaction with oxidizing fluorinating agents, e. g. XeF2, BrF3, or AgF2, 2 is the primary product. Cleavage of the ring system at one of the S=N bonds gives the bifunctional ethane derivatives ClNCClCF2NSF2 (5), ClNCFCF2NSF2 (6), Cl2NCF2CF2NSF2 (7), and (=NCF2CF2NSF2)2 (8).
    Notes: Durch Umsetzung der Titelverbindung 1 mit KF in Sulfolan werden 3-Chlor-4-fluor-(2) und 3,4-Difluor-1,2,5-thiadiazol (3) erhalten. Die Reaktionen mit oxidierenden Fluorierungsmitteln wie XeF2, BrF3 oder AgF2 führen über 2 als Zwischenprodukt zur Spaltung des Ringsystems an einer der S=N-Bindungen. Dabei entstehen die bifunktionellen Ethanderivate CINCCICF2NSF2 (5), ClNCFCF2NSF2 (6), Cl2NCF2CF2NSF2 (7) und (=NCF2CF2NSF2)2 (8).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19821150610
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  • 2
    Electronic Resource
    Electronic Resource
    Die HgF2-assistierte Addition der CF3S-Gruppe an die CN-Dreifachbindung (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 1675-1677 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The HgF2-Assisted Addition of the CF3S Group to the CN Triple BondIn the presence of HgF2 the sulfenyl chloride CF3SCl adds to the triple bond of ClCN to give (CF3S)2NCF3 (9). From CF3SCl and CF3CN bzw. CCl3CN the mono-addition products CF3CF—NSCF3 (6) and CCl3CF—NSCF3 (12) are formed in high yield. 6 and 12 are readily oxidized by HgF2/X2 (X = Cl, Br) to give the sulfur(IV) derivatives C2F5N=S(F)CF3 (7) and CCl3CF2N=S(F)CF3 (17), respectively.
    Notes: CF3SCl wird in Gegenwart von HgF2 an die CN-Dreifachbindung von ClCN addiert unter Bildung von (CF3S)2NCF3 (9). Aus CF3SCl und CF3CN bzw. CCl3CN entstehen die Mono-Additionsprodukte CF3CF=NSCF3 (6) bzw. CF3CF=NSCF3 (12) in hohen Ausbeuten. 6 und 12 werden unter milden Bedingungen durch HgF2/X2 (X = Cl, Br) zu den Schwefel(IV)-Derivaten C2F5N=S(F)CF3 (7) bzw. CCl3CF2N=S(F)CF3 (17) oxidiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871201011
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  • 3
    Electronic Resource
    Electronic Resource
    Über die Chlor- und Brom-Fluorierung acyclischer und cyclischer CN-Mehrfachbindungssysteme (1986)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 119 (1986), S. 107-115 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chloro- and Bromo-Fluorination of Acyclic and Cyclic CN Multiple Bond SystemsFrom nitriles R—C≡N [R = NSF2 (1), NSOF2 (9)] and Cl2 or Br2 in the presence of HgF2 N,N-dihalo-1,1-difluoromethanamines R—CF2—NXX′ [R = NSF2, X = X′ = Cl, Br; X = Cl, X′ = Br (5b, 6, 7); R = NSOF2, X = X′ = Cl, Br; X = Cl, X′ = Br (14, 15, 16)] are obtained. These on photolysis give diazenes (R—CF2—N=)2 [R = NSF2, NSOF2 (8, 17)]. N-(Difluoro-λ4-sulfanylidene)-2-(haloimino)ethanamine derivatives F2SN—CF2—CF=NX [X = Cl, Br (20, 21)] and N-(difluoro-λ4-sulfanylidene)-N′,N′-dihalo-1,2-ethanediamines F2SN—CF2—CF2—NXX′ [X = X′ = Cl, Br; X = Cl, X′ = Br (22-24)], respectively, are prepared on the same route by cleavage of 3,4-difluoro-1,2,5-thiadiazole (18). The diazene (F2SN—CF2—CF2—N=)2 (28) is formed by subsequent photolysis. Under the conditions of this chloro-fluorination in (NCF)3 (29) the cyclic structure is stable, (CINCF2)3 (30) is isolated in high yield.
    Notes: Durch Umsetzung der Nitrile R—C≡N [R = NSF2 (1), NSOF2 (9)] mit Cl2 bzw. Br2 in Gegenwart von HgF2 werden die entsprechenden N,N-Dihalogen-1,1-difluormethanamine R—CF2-NXX′ (R = NSF2, X = X′ = Cl, Br; X = Cl, X′ = Br (5b, 6, 7); R = NSOF2, X = X′ = Cl, Br; X = Cl, X′ = Br [(14, 15, 16)] dargestellt. Aus ihnen bilden sich durch Photolyse die Diazene (R—CF2—N=)2 [R = NSF2, NSOF2 (8, 17)]. N-(Difluor-λ4-sulfanyliden)-2-(halogenimino)ethanamin-Derivate F2SN—CF2—CF=NX [X = Cl, Br (20, 21)] bzw. N-(Difluor-λ4-sulfanyliden)-N′,N′-dihalogen-1,2-ethandiamine F2SN—CF2—CF2—NXX′ [X = X′ = Cl, Br; X = Cl, X′ = Br (22-24)] entstehen auf gleichem Wege durch Spaltung von 3,4-Difluor-1,2,5-thiadiazol (18). Das Diazen (F2SN—CF2—CF2—N=)2 [(28)] ist ebenfalls als Folgeprodukt erhältlich. In (NCF)3 (29) bleibt unter den Bedingungen dieser Chlorfluorierung das Ringgerüst erhalten, und (CINCF2)3 (30) wird in hohen Ausbeuten isoliert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19861190111
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  • 4
    Electronic Resource
    Electronic Resource
    Synthese und Eigenschaften von N,N-Dihalogen-1,1-difluoraminen R—CF2—NXX′ (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 4459-4472 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Properties of N,N-Dihalo-1,1-difluoroamines R—CF2—NXX′The nitriles X—CN (1a-4a, X = Cl, CF3, CCl3, CH3) react with chlorine and bromine to form N,N-dihalo-1,1-difluoroamines R—CF2—NX2 (R = F, CF3, CCl3, CH3; 1d-4d: X = Cl; 1e-4e: X = Br) in high yields. Routes are shown for the synthesis of bromochloroamines RCF2NBrCl (1g-4g), which could not be isolated in pure state. For the ethyl derivatives the imines R—CF = NX (2b-4b: X = Cl; 2c-4c: X = Br) were obtained in good yields by using the appropriate stoichiometry. Both thermolysis and photolysis of the amines give the diazenes (R—CF2—N=)2 (1f-4f).
    Notes: Aus der Umsetzung der Nitrile X—CN (1a-4a, X = Cl, CF3, CCl3, CH3) mit Chlor und Brom lassen sich die N,N-Dihalogen-1,1-difluoramine R—CF2—NX2 (R = F, CF3, CCl3, CH3; 1d-4d: X = Cl, 1e-4e: X = Br) in hohen Ausbeuten darstellen. Synthesewege zu den nicht in reiner Form isolierten Bromchloraminen RCF2NBrCl (1g-4g) werden aufgezeigt. Im Falle der Ethylverbindungen lassen sich durch Wahl der Stöchiometrie die Imine RCF = NX (2b-4b: X = Cl; 2c-4c: X = Br) erzeugen. Sowohl Thermolyse als auch Photolyse der Amine führt zu den Diazenen (R-CF2-N=)2 (1f-4f).
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181117
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