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  • 1
    Electronic Resource
    Electronic Resource
    Tieffarbige Pseudooxo-Krokonsäurebisamide (1982)
    Springer
    Monatshefte für Chemie 113 (1982), S. 1045-1058 
    Details
    ISSN: 1434-4475
    Keywords: 4,5-Bis-(alkyl,aryl)amino-2-dicyanomethylene-cyclopentene-1,3- dione ; 4,5-Dichloro-2-dicyanomethylene-4-cyclopentene-1,3-dione ; Dyes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract 4,5-Dichloro-2-dicyanomethylene-4-cyclopenten-1,3-dione (2) is synthesized by partial Retro-Michael addition of tetracyanoethylene to 4,5-dichloro-4-cyclopentene-1,3-dione. Compound2 is a new electron acceptor, withN-methyl-benzthiazolone-2-hydrazone giving a charge-transfer complex (6). Nucleophilic substitution of2 by pyrrolidine, morpholine and piperidine leads to deeply coloured bisamides7,8. With aromatic amines bisamides are formed too (11), but monosubstitution products can be isolated.N,N-Dimethylaniline reacts with2 by elimination of hydrogen chloride, leading to aN,N-dimethylaminophenyl monosubstitution product of2. The bisamides are green-blue compounds with intense violet colour in solution. The dyes can be classified as pseudooxo croconic acid bisamides, the new type of chromophore is discussed by13C-spectroscopy and quantum chemical calculations (CNDO-CI).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00799246
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  • 2
    Electronic Resource
    Electronic Resource
    Isomere Diamino-alkoxy-pyridin-carbonitrile — ihre Trennung und Verwendung als Kupplungskomponenten (1983)
    Springer
    Monatshefte für Chemie 114 (1983), S. 973-982 
    Details
    ISSN: 1434-4475
    Keywords: Azo Dyes ; Diamino-alkoxy-pyridine-carbonitriles ; UV-VIS spectra
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The isomeric 4,6-diamino-2-alkoxy- (3), and 2,4-diamino-6-alkoxy-3-pyridine-carbonitriles (4) are obtained by treatment of 2-amino-1,1,3-tricyanopropene (1) with sodium alkoxides. Separation is based on their differentpK a -values (3 a=2.01,4 a=4.17). Coupling reaction of3 a-c with benzenediazonium chloride in strong acidic medium leads to the yellow azo dyes5 a-c, whereas coupling of4 a requires a buffered solution (pH 4–6) to yield6. The UV-VIS spectra of the isomer pyridines and the azo dyes are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00799957
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  • 3
    Electronic Resource
    Electronic Resource
    Alkoholyse aromatischer Carbonsäureester (1984)
    Springer
    Monatshefte für Chemie 115 (1984), S. 1185-1197 
    Details
    ISSN: 1434-4475
    Keywords: Mono and polycarboxylic esters ; Metal salt catalysis ; Kinetics ; Chromatographic analysis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The alcoholysis of various esters of aromatic carboxylic esters with octadecanol in the presence of lead stearate was investigated by chromatographic analysis of the reaction mixtures. The reactivity of the esters was found to be strongly affected by the substitution pattern of the aromatic nucleus as well as by the structure of the alkoxy group. Electron donating substituents in a suitable position lead to a remarkable increase in reactivity compared to the unsubstituted alkyl esters.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809350
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  • 4
    Electronic Resource
    Electronic Resource
    Ein Beitrag zur Chemie des 2,3-Dihydro-3-oxo-benzo[b]thiophen-1,1-dioxids Synthesen mit Nitrilen, 86. Mitt. (1990)
    Springer
    Monatshefte für Chemie 121 (1990), S. 299-309 
    Details
    ISSN: 1434-4475
    Keywords: 3-Dicyanomethylene-2,3-dihydro-benzo[b]thiophene-1,1-dioxide ; Benzo[b]thieno[2,3-d]thiophene-8,8-dioxide ; Benzo[4,5]thieno[2,3-c]pyridazine-9,9-dioxide ; 1,2-Dihydro-1-oxo-1H-benzo[4,5]thieno[2,3-c]pyridine-9,9-dioxide ; Benzo[4,5]thieno[2,3-c]pyridine-9,9-dioxide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 2,3-Dihydro-3-oxo-benzo[b]thiophen-1,1-dioxide (1) reacts as CH-acidic component with amidines of orthoesters and anilines resp. to give the anilinomethylene derivates3, 4, and5. With triethyl orthoformiate the hydroxymethylene-compound7 is obtained. Anilino- and phenylhydrazino derivates8 and9 prove the carbonyl activity of1, azo-coupling leads to10, whereas treatment of1 with sulfur and malononitrile yields the benzo[b]thieno[2,3-d]thiophenes11. Introduction of substituents with active NH-functions in position 2 of the dicyanomethylene-product2, such as azocoupling, reaction with phenyl isocyanate and formation of enamines, leads to ring closure reactions between a nitrile and the NH-group. Thereby the phenyl-benzo[4,5]thieno[2,3-c]pyridazines12, the phenyl-1H-benzo[4,5]thieno[2,3-c]pyridines13 and the phenylamino-benzo[4,5]thieno[2,3-c]pyridines14 are obtained.13C and15N-NMR spectroscopy was used as proof of the ring closure reactions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00808932
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  • 5
    Electronic Resource
    Electronic Resource
    Diphenyldiaza-18-krone-6-bis-pyrazoliden-acetonitril, ein neuer Chromoionophor Synthesen mit Nitrilen, 90.Mitt. (1992)
    Springer
    Monatshefte für Chemie 123 (1992), S. 581-585 
    Details
    ISSN: 1434-4475
    Keywords: 7,16-Diphenyl-1,4,10,13-tetraxoxa-7,16-diaza-cyclooctadecan ; Dicyanomethylene-pyrazolinone ; Chromoionophores by thermolysis or photolysis ; Complex formation constants
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary An improved synthesis of 7,16-diphenyl-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadecan (5) is presented and the reaction with 4-dicyanomethylene-3-methyl-1-phenyl-2-pyrazolin-5-on to the colorless adduct6 described. By heating or photolysis6 can be converted to the deeply colored polymethine7. Complex formation constants with potassium ion by1H-NMR-measurements have been determined.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00816852
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  • 6
    Electronic Resource
    Electronic Resource
    Cyanoacetaldehyde — New synthetic applications of an old compound syntheses with nitriles, XCI (1993)
    Springer
    Monatshefte für Chemie 124 (1993), S. 199-207 
    Details
    ISSN: 1434-4475
    Keywords: Cyanoacetaldehyde ; Hydrazones ; Cyanopyrazoles ; Aminopyrazoles
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Verschiedene Umsetzungen mit Cyanacetaldehyd (1), welcher durch Ozonolyse von (E)-1,4-Dicyanbuten oder Allylcyanid hergestellt wurde, werden beschrieben. Reaktion von1 mit Anilinen führt zu den β-Phenylaminoacrylnitrilen2a–e. Umsetzungen von1 mit Hydrazinen ergeben die entsprechenden Hydrazonderivate3a–e, welche unter alkalischen Bedingungen zu den 5-Aminopyrazolen4a–d cyclisiert werden können. Ein Aldol-ähnliches Kondensationsprodukt5a wird durch Reaktion von1 mit Natriumphenolat erhalten. Erhitzen von1 in Dimethylformamiddimethylacetal führt zur Bildung von (E)-3-Dimethylamino-2-formylpropennitril (6), ein wichtiges Zwischenprodukt für organische Synthesen. Die Struktur kann mit NOE-Experimenten geklärt werden. Reaktion von6 mit Hydrazinen führt zu 1-substituierten 4-Cyanpyrazolen7a–k.
    Notes: Summary Various reactions of cyanoacetaldehyde (1), freshly prepared by ozonization of (E)-1,4-dicyano-2-butene or allylcyanide, are described. Thus, conversion of1 with anilines gave β-phenylaminoacrylonitriles2a–e. Reaction of1 with hydrazines led to the corresponding hydrazones3a–e, which could be cyclized under alkaline conditions to 5-aminopyrazoles4a–d. An aldol-type condensation product5a could be obtained by reaction of1 with sodiumphenoxide. Treatment of1 with dimethylformamide-dimethylacetal led to the formation of (E)-3-dimethylamino-2-formylpropenenitrile (6), a very useful synthon in synthetic chemistry. For the determination of the structure of6 the method of steady state differential NOEs was used. Reaction of6 with hydrazines gave 1-substituted-4-cyanopyrazoles7a–k.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00808679
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  • 7
    Electronic Resource
    Electronic Resource
    Synthese und Fluoreszenzeigenschaften von cyansubstituierten 2-Aminopyridinen (1981)
    Springer
    Monatshefte für Chemie 112 (1981), S. 973-985 
    Details
    ISSN: 1434-4475
    Keywords: 3,5-Dicyanopyridines ; 3,4,5-Tricyanopyridines
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The synthesis of several 2-aminopyridines is described. The reaction of tetracyanoethylene with 3-imino-propane-carbonitrile gives 2-amino-3,4,5-tricyano-pyridines with alkyl and aryl-substituents, resp., in position 6. Nucleophilic substitution of 2-amino-6-chloro-3,5-dicyanopyridines and 2-amino-6-chloro-3,4,5-tricyano-pyridines with phenolates leads to a variety of pyridines. Spectroscopical data of absorption and fluorescence are presented and the influence of the cyano groups is discussed. The results are in good agreement with quantum chemical calculations (PPP).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00905068
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  • 8
    Electronic Resource
    Electronic Resource
    Chelatbildende Enaminoketone I. Synthese von unsymmetrischen Liganden (1984)
    Springer
    Monatshefte für Chemie 115 (1984), S. 1353-1368 
    Details
    ISSN: 1434-4475
    Keywords: Chelating agents ; Chelating polymers ; Tridentate ligands
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Syntheses of chelating enaminoketones for a potential use in enrichment or recovery of metals from their aqueous solutions are described. Tridentate ligands were prepared either from aromatic amines, triethoxymethane and cyclic 1,3-dicarbonyl compounds in a one-step synthesis, or from the anilinomethylene compounds obtained by this approach and aliphatic amines. Polymerizable ligands have also been synthesized by reaction with (meth)acryloyl chloride and copolymerized with styrene to yield a chelating polymer.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00798314
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  • 9
    Electronic Resource
    Electronic Resource
    Ricinin — einfach synthetisiert (1984)
    Springer
    Monatshefte für Chemie 115 (1984), S. 1467-1470 
    Details
    ISSN: 1434-4475
    Keywords: 4-Methoxy-1-methyl-2(1H)-pyridone-3-carbonitrile ; Alkaloid synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Cyclization of 1,1-dicyano-4-(N,N-dimethylamino)-2-methoxy-1,3-butadiene leads to 4-methoxy-2(1H)-pyridone-3-carbonitrile and 2,4-dimethoxy-pyridine-3-carbonitrile. Methylation of both products yields ricinine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00816346
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, 85. Mitt.: Über 4-Dicyanmethylen-und 4-Tricyanpropyliden-homophthalimide (1990)
    Springer
    Monatshefte für Chemie 121 (1990), S. 189-193 
    Details
    ISSN: 1434-4475
    Keywords: Cyanomethylene compounds ; Retro Michael addition ; Tetracyanoethylene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary Addition of tetracyanoethylene to the 1,2,3,4-tetrahydro-isoquinoline-1,3-diones1 a–d yields 4-(dicyanomethylene)-1,2,3,4-tetrahydro-isoquinoline-1,3-diones3 or 4-(2-amino-1,1,3-tricyano-3-propylidene)-1,2,3,4-tetrahydro-1,3-diones4 depending on the substituent in position 2. Spectra of both types of derivatives are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809531
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