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  • 1
    Electronic Resource
    Electronic Resource
    1,6;8,13-Propandiyliden-[14]annulen (1970)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 82 (1970), S. 512-513 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19700821305
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  • 2
    Electronic Resource
    Electronic Resource
    1,6:8,13-Propanediylidene[14]annulenePresented by E. Vogel in a lecture at the GDCh General Meeting at Hamburg in September 1969.Formerly named 1,6:8,13-propano[14]annulene. (1970)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 9 (1970), S. 514-516 
    Details
    ISSN: 0570-0833
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.197005141
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  • 3
    Electronic Resource
    Electronic Resource
    Das Experiment: Die Zink-Luft-Batterie (1972)
    Weinheim : Wiley-Blackwell
    Chemie in unserer Zeit 6 (1972), S. 128-131 
    Details
    ISSN: 0009-2851
    Keywords: Chemistry ; Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ciuz.19720060405
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  • 4
    Electronic Resource
    Electronic Resource
    Das Experiment: Elektrochemische Direkterzeugung pulsierender Spannungen (1974)
    Weinheim : Wiley-Blackwell
    Chemie in unserer Zeit 8 (1974), S. 173-176 
    Details
    ISSN: 0009-2851
    Keywords: Chemistry ; Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ciuz.19740080603
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  • 5
    Electronic Resource
    Electronic Resource
    Polyacetylenverbindungen, 224. Synthese des Ichthyotherol-acetats (1974)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 654-656 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Polyacetylenic Compounds, 224. Synthesis of Ichthyotherol AcetateStarting with the triyne-diene 3 the tetrahydropyran derivative 6 is obtained via the epoxide 4, which on esterification yields 7. The acetate is identical in all spectroscopic data with the natural product. The structure of the epoxide 5 has also been established by synthesis of the racemate.
    Notes: Ausgehend von dem Trindien 3 erhält man über das Epoxid 4 das Tetrahydropyranderivat 6, das nach Veresterung 7, liefert. Das Acetat ist in allen spektroskopischen Eigenschaften identisch mit dem Naturstoff. Die Struktur des Epoxids 5 wird ebenfalls durch Synthese des Racemats sichergestellt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19741070237
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  • 6
    Electronic Resource
    Electronic Resource
    Pyrazolo[3.4-c]carbazole aus Cyclohexandion-(1.4)-bis-phenylhydrazon (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 3302-3318 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Pyrazolo[3.4-c]carbazoles from 1.4-Cyclohexanedione Bis(phenylhydrazone)The products of the reaction of 1.4-cyclohexanedione bis(phenylhydrazone) in 70perc. methanol or ethanol/n)H2SO4 are, in addition to 2 and 3, Maynly 3-aminocarbazole (4) (with a little of the corresponding sec. amine 30) and the tetrahydro-pyrazolo[3.4-c]carbazoles 10 or 11, respectively. These latter compounds arise by condensation of the hypothetical 3-phenylhydrazonocarbazole 7 with formaldehyde or acetaldehyde formed by concomitant dehydrogenation of the solvent (phenylhydraziniumion as oxidant). Addition of these aldehydes to the reaction mixture raises the yields of 10 and 11 considerably. Benzaldehyde correspondingly gives rise to the formation of 12.10-12 can be dehydrogenated (16,17) and can undergo oxidation as well as degradation with ring opening (ketolactams 19-22, carboxylic acids 23 and 27, ketoester 24, lactone 25). - Permanganate in acetone transforms 11 to the dimer 28 with one pyrazole ring opened. - The spectra of the aforementioned compounds together with the Nuclear Overhauser Effect permit a decision in favor of an angular rather than a linear junction of the pyrazole and carbazole systems.
    Notes: Cyclohexandion-(1.4)-bis-phenylhydrazon (1) reagiert in 70proz. Methanol oder Äthanol/ nH2SO4 außer zu 2 und 3 zu 3-Amino-carbazol (4) und wenig sek. Amin 30 sowie zu den Tetrahydro-pyrazolo[3.4-c]carbazolen 10 bzw. 11. Diese entstehen durch Kondensation des hypothetischen 3-Phenylhydrazono-carbazols 7 mit dem aus dem Lösungsmittel durch Dehydrierung (Phenylhydrazin-Kation) gebildeten Form- und Acetaldehyd. Zusatz dieser Aldehyde zum Reaktionsgemisch erhöht die Ausbeute an 10 und 11. Benzaldehyd liefert analog 12. - 10-12 lassen sich dehydrieren (16, 17) und unter Ringspaltung oxydieren sowie abbauen (Ketolactame 19-22, Carbonsäuren 23 und 27, Ketoester 24, Lacton 25). Permanganat in Aceton führt 11 unter NN-Verknüpfung in das Dimere 28 mit geöffnetem Pyrazolring über. -Die Spektren der vorgenannten Verbindungen erlauben zusammen mit dem Nuclear-Overhauser-Effekt, zu Gunsten einer angulären statt linearen Verknüpfung von Pyrazol- und Carbazol-System zu entscheiden.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701031034
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  • 7
    Electronic Resource
    Electronic Resource
    Fragmentierungsreaktionen an Carbonylverbindungen mit β-ständigen elektronegativen substituenten, XXVI. Reaktion von 1-(Tosyloxymethyl)- und 1-(Trifluormethylsulfonyl-oxymethyl)bicyclo[3.3.1]nonan-9-on mit Nucleophilen (1974)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 2176-2185 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Fragmentation Reactions of Carbonyl Compounds with Electronegative substituents in the β-Position, XXVI. Reactions of 1-(Tosyloxymethyl)- and 1-(Trifluoromethylsulfonyloxymethyl)bicyclo[3.3.1]nonan-9-one with NucleophilesThe bicyclic ketotosylate 8 and the triflate 9 were synthesized starting from the ketoester 3. 8 and 9 react with methanolic NaOH, potassium tert-butoxide, NaNH2, NaC≡CH, and CH3Li with fragmentation to yield the 5-methylenecyclooctane derivatives 14-20. Whereas direct substitution of 8 occurs only with cyanide ions in DMSO to 10, neopentyl substitution of the triflate 9 is also possible with acetate, azide, and the dimedone anion (→11-13). NaBH4 reduction of 8 leads to the formation of the tosyloxy alcohol 25, which reacts with NaHCO3 in DMSO to give the tricyclic carbonate 26.
    Notes: Ausgehend vom Ketoester 3 wird das bicyclische Ketotosylat 8 und das Triflat 9 dargestellt. 8 und 9 reagieren mit methanolischer NaOH, Kalium-tert-butylat. NaNH2, NaC ≡ CH und CH3Li unter Fragmentierung zu den 5-Methylencyclooctan-Derivaten 14-20. Während 8 nur durch Cyanid-lonen in DMSO zu 10 substituiert wird, tritt bei 9 auch mit dem Acetat-, Azid- und Dimedon-Anion Neopentylsubstitution zu 11-13 ein. Durch NaBH4-Reduktion von 8 wird der Tosyloxyalkohol 25 erhalten, dessen Umsetzung mit NaHCO3 in DMSO zum tricyclischen Carbonat 26 führt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19741070706
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  • 8
    Electronic Resource
    Electronic Resource
    Synthese von α-Methylen-δ-lactonen (1974)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 2852-2859 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of α-Methylene-δ-lactonesReaction of enamines of alicyclic and cyclic ketones 2a-g with 2-(bromomethyl)acrylate 1 in dioxane affords α,β-unsaturated esters 3a-g. Saponification, NaBH4-reduction, and dehydration leads lead to α-methylene-δ-lactones 5a-g.
    Notes: Durch Umsetzung von Enaminen Offenkettiger und cyclischer Ketone 2a-g mit 2-(Brommethyl)acrylsäureestern 1 in Dioxan (→3a-g), Verseifung, NaBH4-Reduktion und Wasserabspaltung werden die α-Methylen-δ-lactone 5a-g dargestellt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19741070907
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  • 9
    Electronic Resource
    Electronic Resource
    Heterohelicene aus Cyclohexandion-(1.4)-bis-phenylhydrazon (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 3319-3342 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterohelicenes from 1.4-Cyclohexanedione Bis(phenylhydrazone)The helicenes 8 and 6 have been isolated from the brick-red product formed by treatment of 1.4-cyclohexanedione bis(phenylhydrazone) with alcoholic n H2SO4. 8 can be dehydrogenated (9) and acetylated to the triacetyl derivative 12 which contains the ring system 8a. Catalytic hydrogenation of 8 with deamination results in the formation of the diindolocarbazole 15, a dihydro-derivative of 6. Hydrogen peroxide in alkaline solution oxidizes 8 to the anthranilate of an indolocinnolone-propionic acid (16a; methyl ester: 16b) which is split by ethanolic hydrochloric acid to form the ester 19b. Bromination of 16a yields the tribromo derivative 20. The prim. amine 22 (or 23) is formed as a by-product of oxidation. The dehydro-compound 9 is degraded by hydrogen peroxide to give the indolocinnolone-carboxylic acid 19a. - 1.4-Cyclohexanedione reacts with 3-aminocarbazole to form the quinonediimine 11 (via 10), an isomer of 8. - The assumption of a helicene structure for 8, 9, 12, 6, and 15 is based on the n. m. r. spectra and, in the case of 8 and 12, on partial resolution of the racemate.
    Notes: Aus dem bei der Umsetzung von Cyclohexandion-(1.4)-bis-phenylhydrazon mit alkoholischer n H2SO4 gebildeten rotbraunen Hauptprodukt werden die Helicene 8 und 6 isoliert. 8 läßt sich zu 9 dehydrieren und mit Acetanhydrid zu dem von der isomeren Form 8a abgeleiteten Triacetat 12 acetylieren. Unter reduktiver Desaminierung liefert die katalytische Hydrierung von 8 das Diindolo-carbazol 15, ein Dihydroderivat von 6. Durch alkalisches Wasserstoffperoxid wird 8 unter Ringöffnung zum Anthranilat einer Indolo-cinnolon-propionsäure (16a; Methylester: 16b) oxydiert, das von äthanolischer Salzsäure zum Ester 19b gespalten wird. Bromierung von 16a liefert das Tribrom-Derivat 20. Als Nebenprodukt der Oxydation wird das prim. Amin 22 (oder 23) gefaßt. Die Dehydroverbindung 9 wird von Wasserstoffperoxid zur Indolo-cinnolon-carbonsäure 19a abgebaut. - Aus Cyclohexandion-(1.4) läßt sich mit 3-Amino-carbazol über die Zwischenstufe 10 das zu 8 isomere Chinondiimin 11 synthetisieren. - Die Annahme einer Helicen-Struktur wird bei 8, 9, 12 sowie bei 6 und 15 mit dem NMR-Spektrum begründet, bei 8 und 12 auch durch partielle Racemat-Spaltung.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701031035
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  • 10
    Electronic Resource
    Electronic Resource
    1,6;8,13-Butandiyliden-[14]annulen (1970)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 82 (1970), S. 513-514 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19700821306
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