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  • 1
    Electronic Resource
    Electronic Resource
    Einige neue 3.4-disubstituierte Indolderivate (1960)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 93 (1960), S. 2024-2028 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ausgehend von 4-Cyanmethyl-indol wurde eine Reihe 3.4-disubstituierter Indolderivate hergestellt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19600930917
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  • 2
    Electronic Resource
    Electronic Resource
    Benz[cd]indolderivate (1960)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 93 (1960), S. 2029-2034 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Durch Dieckmann-Kondensation des Indol-diessigsäure-(3.4)-diäthylesters und des N-Benzoyl-2.3-dihydro-indol-diessigsäure-(3.4)-diäthylesters werden die entsprechenden Benz[cd]indolderivate dargestellt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19600930918
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  • 3
    Electronic Resource
    Electronic Resource
    Reaktionen an Indolderivaten, XXXIII. Eine einfache und biogeneseorientierte Totalsynthese von Brevicollin und Brevicarin (1977)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 110 (1977), S. 2424-2432 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions with Indole Derivatives, XXXIII. A Simple and Biogenetically Orientated Total Synthesis of Brevicolline and BrevicarineA simple synthesis of a pyrrolidine-substituted tryptamine (6) is reported which is serving as a starting material for brevicolline (1) as well as brevicarine (2). The biogenetical interrelations are discussed.
    Notes: Es wird eine einfache Synthese für ein pyrrolidinsubstituiertes Tryptamin (6) beschrieben, das als Ausgangsmaterial zur Synthese für sowohl Brevicollin (1) als auch Brevicarin (2) dienen kann. Die biogenetischen Zusammenhänge werden diskutiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19771100703
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  • 4
    Electronic Resource
    Electronic Resource
    On the identification numbers for chemical structures (1986)
    New York, NY : Wiley-Blackwell
    International Journal of Quantum Chemistry 30 (1986), S. 173-183 
    Details
    ISSN: 0020-7608
    Keywords: Computational Chemistry and Molecular Modeling ; Atomic, Molecular and Optical Physics
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Several identification (ID) numbers for chemical structures (connectivity ID number, prime ID number, weighted ID number) are analyzed and tested until a counterexample (a pair of structures with the same ID number) is found. The analysis is carried out for acyclic structures with up to 20 atoms, trees with up to 20 points, benzenoid graphs and polyhexes with up to 10 hexagons, and all connected graphs with up to 6 points.Although all the (chemical) ID numbers studied are highly selective for many families of (molecular) graphs, none of them are unique: in all three cases the counterexamples are found. However, the greatest discriminative power is shown by the weighted ID number.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/qua.560300718
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  • 5
    Electronic Resource
    Electronic Resource
    Aminosäuren, 10 Zur Reaktion von Pyroglutaminsäure-Derivaten mit Thionyl- und Oxalylchlorid (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 55-59 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of N-methyl- and N-benzyl-substituted 5-oxoproline methylesters (1a, b) with thionyl or oxalyl chloride yield N-substituted 5-chloro-2,3-dihydro-1H-pyrrole-2-carboxylic esters. These esters, as α-chloro enamines, undergo further electrophilic reaction in the ß-position by thionyl or oxalyl chloride. Thus, N-substituted bis(pyrrolyl) thioethers 2, bis(pyrrolyl) disulfides 3, and their oxidation products 4,5, and 6 are formed with excess thionyl chloride. N-substituted 5-chloro-4-[chloro(chlorocarbonyl)methyl]-1H-pyrrole-2-carboxylic esters 12 are obtained with oxalyl chloride. Reaction of L-1-benzhydryl-5-oxoproline methylester (L-1c) with thionyl chloride results in the formation of N-unsubstituted bis(pyrrolyl) thioether 9 under comparable conditions.
    Notes: N-Methyl- und N-Benzyl-substituierte 5-Oxoprolin-methylester (1a, b) bilden mit Thionyl- bzw. Oxalychlorid N-substituierte 5-Chlor-2,3-dihydro-1H-pyrrolcarbonsäureester, die als α-Chlor-enamine in ß-Position elektrophil mit Thionylchlorid bzw. Oxalylchlorid weiterreagieren: mit Thionylchlorid zu N-substituierten Bis(pyrrolyl)thioethern 2 und Bis(pyrrolyl)disulfiden 3 sowie deren Oxidationsprodukten 4, 5 und 6, mit Oxalylchlorid zu N-substituierten 5-Chlor-4-[chlor(chlorcarbonyl)methyl]-1H-pyrrol-2-carbonsäureestern 12. Die Umsetzung von L-1-Benzhydryl-5-oxo-prolin-methylester (L-1c) mit Thionylchlorid führt unter vergleichbaren Bedingungen zum N-unsubstituierten Bis(pyrrolyl)thioether 9.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871200110
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  • 6
    Electronic Resource
    Electronic Resource
    Photoreaktionen mit Fulleren-C60 [3 + 2]-Photocycloaddition von 2,3-Diphenyl-2H-azirin (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 787-789 
    Details
    ISSN: 0009-2940
    Keywords: Fullerenes ; Azirines ; Photochemistry ; [3 + 2] Cycloadditions ; Electron transfer reactions ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Photoreactions with C60-Fullerene. [3 + 2] Photocycloaddition of 2,3-Diphenyl-2H-azirineUpon irradiation 2,3-Diphenyl-2H-azirine (2) is added to C60 1 with formation of mono and oligo adducts. 1,9-(3,4-Dihydro-2,5-diphenyl-2H-pyrrolo)fulleren-60 (3) has been isolated and identified by standard spectroscopic methods. Mechanistic studies revealed two reaction paths leading to 3, i.e. the classic 1,3-dipolar cycloaddition via the nitrile ylide 4 (direct irradiation) or a route via 2-azaallenyl radical cations 5 (sensitization by photoinduced electron transfer).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270431
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  • 7
    Electronic Resource
    Electronic Resource
    Chemistry of the Higher Fullerenes: Preparative isolation of C76 by HPLC and synthesis, separation, and characterization of Diels-Alder monoadducts of C70 and C76 (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1689-1706 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: HPLC Separation of higher fullerenes was compared on two different stationary phases, and the preparative isolation of pure C76 is described. Higher-fullerene derivatives 1 and 2 were prepared by Diels-Alder reaction of C70 and C76 with an ortho-quinodimethane intermediate generated in situ. Three out of four possible isomeric C70 monoadducts, i.e. 1a-c, and, for the first time, one isomeric C76 monoadduct, i.e. 2c, could be isolated in pure form and characterized by 1H-NMR, 13C-NMR, UV/VIS, and mass spectrometry. Five other C76 isomers i.e., 2a,b,d-f were obtained in partially separated product fractions. Coalescence temperatures and energy barriers were determined for the cyclohexene-ring inversion in two of the isomeric C70 derivatives. The structure of the C70 adducts could be deduced unambiguously from symmetry considerations based on high- and low-temperature 1H-NMR spectroscopy. A simple model for the qualitative evaluation of the local curvature of fullerene surfaces is presented and used for the prediction of addition sites in higher fullerenes. These predictions are compared to the experimental results mentioned above as well as to predictions resulting from π-bond-order considerations and from calculated pyramidalization angles.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770703
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  • 8
    Electronic Resource
    Electronic Resource
    An analysis of the electronic structure of 6,7-dimethyl-3-oxabicyclo[3.2.0]hepta-1,4,6-triene (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 3939-3943 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Analyse der elektronischen Struktur von 6,7-Dimethyl-3-oxabicyclo[3.2.0]hepta-1,4,6-trienDie Geometrie und π-Elektronenstruktur von 6,7-Dimethyl-3-oxabicyclo[3.2.0]hepta-1,4,6-trien (4) wurde mittels MNDO-Rechnungen und des He(I)-Photoelektronenspektrums analysiert. Auf Grund der Alternanz der Bindungslängen kommt dem Molekül olefinischer bzw. antiaromatischer Charakter zu. HOMO und LUMO sind im wesentlichen in der Doppelbindung des Vierrings lokalisiert. Die HOMO-Energie von 7.82 eV deutet auf einen hohen nucleophilen Charakter für 4.
    Notes: The geometry and the π-electronic structure of 6,7-dimethyl-3-oxabicyclo[3.2.0]hepta-1,4,6-triene (4) is analyzed by MNDO calculations and by the interpretation of the He-I-photo-electron spectrum. The calculated bond length alternations in 4 indicate olefinic resp. antiaromatic character. As HOMO and LUMO of 4 are mainly localized in the double bond of the cyclobutene subunit, electrophilic and nucleophilic reactions should occur at this bond. From the HOMO IP of 7.82 eV a high degree of nucleophilic character is to be expected.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181007
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  • 9
    Electronic Resource
    Electronic Resource
    Chemospezifität und Regioselektivität bei der Cycloaddition von Diazoalkanen an 1H-1,2-Diazepine (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 4682-4706 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chemospecificity and Regioselectivity during Cycloaddition Reactions of Diazoalkanes with 1H-1,2-Diazepines1H-1,2-Diazepines 1 react in a chemospecific way, but only regioselectively, at the 4-double bond with diazoalkanes to form “direct” and “inverse” pyrazolinodiazepines (3,4,6-21). A dramatic rate increase is observed when going from diazomethane to diazoethane and to diazoisopropane, a result which agrees quite well with MNDO calculations. Considering the AO coefficients of the frontier MO's which come into interaction during these concerted cycloadditions, the cyclo-additions are unlikely to occur in a regiospecific manner; only a slight regioselectivity is predicted and found in most of the cases. 1-Benzoyldiazepines 1e and f proved to be the fastest reacting educts with no formation of the “inverse” adducts with 1e and only in poor yield with 1f. Diazepines bearing a 3-methyl group have a more pronounced boat-shaped conformation than their non-alkylated homologues. As a consequence, the regioselectivity of the 1,3-dipolar cyclo-additions is decreasing.
    Notes: 1H-1,2-Diazepine 1 reagieren mit Diazoalkanen chemospezifisch, jedoch nur regioselektiv, an der 4-Doppelbildung zu „direkten“ und „inversen“ Pyrazolinodiazepinen (3,4,6-21). Dabei nimmt die Reaktivität von Diazomethan (DAM) über Diazoethan (DAE) zu Diazoisopropan (DAP) deutlich zu, was mit MNDO-Rechnungen in guter Übereinstimmung steht. Nach den AO-Ko-effizienten der Grenzorbitale sollten diese konzertierten Cycloadditionen keine Regiospezifität, sondern nur eine gewisse Regioselektivität aufweisen, was wiederum durch das Experiment bewiesen wurde. Von allen Edukten reagieren die beiden 1-Benzoyldiazepine 1e und f am besten, wobei die „inversen“ Addukte für 1e überhaupt nicht und für 1f nur in geringem Ausmaße auftreten. Eine Methylgruppe in 3-Stellung der Diazepine 1 hat allgemein zur Folge, daß die Wannenkonformation der entsprechenden Diazepine stärker ausgeprägt ist, wobei die Regioselektivität noch abnimmt.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181205
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  • 10
    Electronic Resource
    Electronic Resource
    Aminosäuren, 9 Zur Reaktion von Pyroglutaminsäure-Derivaten mit Phosphorpentachlorid - Darstellung chlorierter Pyrrol-2-carbonsäure-Derivate (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 45-54 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: N-Benzyl-4,5-dichloro-1H-pyrrole-2-carboxylic esters 6 are formed from N-benzyl-5-oxoproline esters 5 and PCl5 via differently chlorinated intermediates. The N-benzhydryl- L-3 and N-acyl-5-oxoproline esters L-4, on the other hand, suffer cleavage of the N-substituent in the course of this reaction sequence to give L-4,4,5-trichloro-3,4-dihydro-2H-pyrrole-2-carboxylic esters 18, which are dehydrohalogenated in the presence of base, yielding 4,5-dichloro-1H-pyrrole-2-carboxylic esters 20. These reactions provide the best access to 4,5-dichloro-1H-pyrrole-2-carboxylic acid derivatives which, in turn, can serve as precursors in the synthesis of pyoluteorin type compounds.
    Notes: N-Benzyl-5-oxoprolinester 5 werden mit PCl5 über verschiedene chlorierte Zwischenstufen zu N-Benzyl-4,5-dichlor-1H-pyrrol-2-carbonsäureestern 6 chloriert, während N-Benzhydryl- L-3 und N-Acyl-5-oxoprolinester L-4 mit PCl5 unter Abspaltung des N-Substituenten L-4,4,5-Trichlor-3,4-dihydro-2H-pyrrol-2-carbon-säureester 18 bilden, die mit Base in die 4,5-Dichlor-1H-pyrrol-2-carbonsäureester 20 übergehen. Diese Umsetzungen stellen die beste Methode zur Herstellung von 4,5-Dichlor-1H-pyrrol-2-carbonsäure-Derivaten, die zur Gewinnung von Verbindungen des Pyoluteorin-Typs dienen können, dar.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871200109
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