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  • 1
    Electronic Resource
    Electronic Resource
    Hydrazin-Reaktionen, XII. Umwandlung von 4-Ulose-hydrazonen in 4-Hydroxy-pyridazine und 3-Ulose-hydrazonen in 4-Hydroxy-pyrazole (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 1846-1854 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Hydrazine Reactions, XII. Reaction of 4-Ulose hydrazones to 4-Hydroxypyridazines and of 3-Ulose hydrazones to 4-Hydroxypyrazoles2,3;5,6-Di-O-isopropylidene-D-xylo-hexos-4-ulose hydrazone dimethylacetal (2) on acid hydrolysis undergoes cyclization to derivatives of 4-hydroxypyridazine (11) and 5-hydroxypyridazine (12). Hydrolysis of the methylhydrazono compound 3 results only in the formation of 5-hydroxypyridazine 13, which can be isolated as the zwitterion 17. Acid hydrolysis of 3,5-dideoxy-3-hydrazino-1,2-O-isopropylidene-D-ribofuranose gives the pyrazole derivative 21. 1,2;5,6-Di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose hydrazone (24) on hydrochloric acid hydrolysis undergoes cyclization to the 4-hydroxypyrazole derivative 28.
    Notes: 2.3;5.6-Di-O-isopropyliden-D-xylo-hexos-4-ulose-hydrazon-dimethylaceta1 (2) cyclisiert bei Säureeinwirkung zu Derivaten des 4-Hydroxy-pyridazins (11) und 5-Hydroxy-pyridazins (12). Die entsprechende Methylhydrazon-Verbindung 3 liefert nur ein 5-Hydroxy-pyridazin 13, das als Zwitterion 17 isolierbar ist. 3.5-Didesoxy-3-hydrazino-1.2-O-isopropyliden-D-ribofuranose (19) ergibt mit Säuren das Pyrazol-Derivat 21. 1.2;5.6-Di-O-isopropyliden-α-D-ribo-hexofuranos-3-ulose-hydrazon (24) cyclisiert bei Hydrolyse mit Salzsäure zum 4-Hydroxy-pyrazol-Derivat 28.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030621
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  • 2
    Electronic Resource
    Electronic Resource
    Hydrazin-Reaktionen, XI. Cyclisierung von 4.5-Didesoxy-4-hydrazino-L-xylose zu einem Sechsring-Hydrazon (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 1834-1845 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Hydrazine Reactions, XI. Cyclization of 4,5-Dideoxy-4-hydrazino-L-xylose to a Six-membered Ring HydrazoneAlkaline treatment of bisulfite adducts 4and 5 yields free 4,5-dideoxy-4 hydrazino L - xylose and - 4 - α - methylhydrazino - L - xylose, which cyclisize in alkaline to neutral solution to give the six-membered ring hydrazones 7 and 8 possessing half - chair conformation. Hydrogenation of 7 yields the acyclic diamine 12 and the hexahydropyridazine derivative 15. The structures of the preferred rotamers of mono - and diacetylhydrazides of hexahydropyridazine derivatives are discussed on the basis of n.m.r data. Treatment of the cyclic hydrazones 7 and 8 with acid results in loss of water with formation of the pyridazines 26 and 28.
    Notes: Freie 4.5-Didesoxy-4-hydrazino- bzw. -4-[α-methyl-hydrazino]-L-xylose sind durch alkalische Spaltung aus ihren Schwefligsäure-Addukten 4 und 5 erhältlich und cyclisieren in alkalischer bis neutraler Lösung zu Sechsring - Hydrazonen 7und 8, die in der Halbsesselkonformation vorliegen. Hydrierung von 7 führt zum offenkettigen Diamin 12 und Hexahydropyridazin - derivat 15. Die Struktur der bevorzugten Rotameren von Monoacetyl- und Diacetyl-hydrazid Gruppierungen in Hexahydropyridazinderivaten wird auf Grund der NMR-Daten diskutiert. Bei Säurebehandlung der cyclischen Hydrazone 7 und 8 erfolgt Wasserabspaltung zu den Pyridazinen 26 und 28.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030620
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  • 3
    Electronic Resource
    Electronic Resource
    Monosaccharide mit stickstoffhaltigem Ring, XXVI Darstellung freier 4-Amino-4-desoxy-D-glucose und 4-Amino-4-desoxy-D-galaktose. Dimerisierung zu Bis-Pyrrolidin-Zuckern (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 1599-1620 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Monosaccharides Containing Nitrogen in the Ring, XXVI. Synthesis of free 4-Amino-4-deoxy-D-glucose and 4-Amino-4-deoxy-D-galactose. Dimerization to Bis-pyrrolidine-sugarsReaction of 2,3;5,6-di-O-isopropylidene-4-p-toluolsulfonyl-D-glucosedimethylacetal (2) with NaN3 yields preferentially the unsaturated compound 3 by elimination and only 10% of the azido-sugar 4 by substitution. Oxidation of 2,3;5,6-di-O-isopropylidene-D-glucosedimethylacetal (1) gives the keto derivative 7, the oxime 8 of which is reduced with LiAlH4 to afford equal amounts of the acyclic amino-sugars 5 + 9 having the galacto- and gluco-configuration, respectively. Separation of the isomers is possible via N-acetates 6 and 10 or bisulfite adducts 11 and 15. In alkaline solution both free 4-amino-4-deoxy-D-glucose and-D-galactose, obtained from 11 or 15, exist as an equilibrium mixture of pyrrolidine-, bis-pyrrolidine-, and pyrroline-forms, the bis-pyrrolidine-forms predominating. The dimeric structures are established by mass spectrometric analysis of the acetates and trimethylsilyl ethers of 21 and 29. In acid solution ring expansion occurs to give pyranose-hydrochlorides of 4-amino-4-deoxy-D-glucose and -D-galactose 14 and 33. 14 is also obtained by acid hydrolysis of methyl-4-amino-4-deoxy-α-D-glucopyranoside.
    Notes: 2.3;5.6-Di-O-isopropyliden-4-p-toluolsulfonyl-D-glucosedimethylacetal (2) reagiert mit NaN3 bevorzugt unter Eliminierung zu 3 und nur zu 10% unter Substitution zum Azido-zucker 4. Durch Oxydation von 2.3;5.6-Di-O-isoproypliden-D-glucosedimethylacetal (1) ist der 4-Ketozucker 7 erhältlich, dessen Oxim 8 mit LiAlH4 die offenkettigen 4-Amino-zucker der galakto und gluco-Konfiguration 5 + 9 im Verhältnis 1 : 1 liefert. Eine Trennung der Isomeren ist über die N-Acetate 6 und 10 oder Schwefligsäure-Addukte 11 und 15 möglich. Bei der freien 4-Amino-4-desoxy-D-glucose und -D-galaktose, aus 11 und 15 erhältlich, überwiegt in alkalischer Lösung die Bis-Pyrrolidin-Form 21 bzw. 29 stark im Gleichgewicht mit der Pyrrolidin- und Pyrrolin-Form. Durch massenspektroskopische Analyse der Acetate und Trimethylsilyl- äther von 21 und 29 werden die dimeren Strukturen gesichert. In saurer Lösung reagieren die Pyrrolidin-Formen unter Ringerweiterung zu Pyranose-hydrochloriden der 4-Amino-4-desoxy-D-glucose und -D-galaktose 14 und 33. 14 ist auch durch saure Hydrolyse von Methyl-4-amino-4-desoxy-α-D-glucopyranosid darstellbar.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030531
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  • 4
    Electronic Resource
    Electronic Resource
    Hydrazinreaktionen, II. Darstellung von 5-Hydrazino-5-desoxy-D-xylose. Umwandlung in N-Amino-D-xylopiperidinose und ein dimeres Hexahydrotetrazin-Derivat (1967)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 100 (1967), S. 2467-2473 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 5-Hydrazino-1.2-O-isopropyliden-5-desoxy-D-xylofuranose (2) liefert mit schwefliger Säure ein 5-Hydrazino-5-desoxy-D-xylose-Schwefligsäure-Addukt (3), das alkalisch zur freien 5-Hydrazino-5-desoxy-D-xylose spaltbar ist. Diese schließt den Halbacetalring in alkalischer Lösung zur N-Amino-D-xylopiperidinose (7). In neutraler Lösung dimerisiert 7 zum Hexahydrotetrazin-Derivat 5. Hydrierung von 7 liefert 1.5-Imino-1.5-didesoxy-D-xylit (9), Reaktion mit Blausäure das Nitril 8. In saurer Lösung in der Hitze kann 7 unter dreifacher Wasserabspaltung zum N-Amino-3-hydroxy-pyridiniumbetain-hydrat (17) reagieren.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19671000802
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  • 5
    Electronic Resource
    Electronic Resource
    Die fördernde Rolle von Phosphinoester-Liganden bei der Synthese neutraler Carben-, Vinyliden- und Allenyliden-Ruthenium(II)-KomplexeHerrn Professor Hubert Schmidbaur zum 60. Geburtstag gewidmet. (1995)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 128 (1995), S. 49-62 
    Details
    ISSN: 0009-2940
    Keywords: Ruthenium(II) complexes, octahedral ; Phosphino esters as mono- and bidentate ligands ; Fluxional behaviour ; Carbene complexes ; Vinylidene complexes ; Allenylidene complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Vinylidene Transition-Metal Complexes, XXXV[1].  -  The Supporting Role of Phosphino Ester Ligands for the Synthesis of Neutral Carbene, Vinylidene and Allenylidene Ruthenium(II) ComplexesThe reaction of [RuCl2(PPh3)3] (1) with the phosphino esters iPr2P(CH2)nCO2R (2-4) leads to complete (n = 1; R = CH3, C2H5) or partial (n = 2; R =CH3) displacement of the PPh3 ligands and formation of the octahedral ruthenium(II) complexes [RuCl2{k2(P,O)-iPr2PCH2CO2R}2] (5, 6) and [RuCl2(PPh3){k(P)-iPr2PCH2CH2CO2Me}{k2(P,O)-iPr2PCH2CH2CO2Me}] (7). Treatment of 5 with LiBr and LiI affords the dibromo- and diiodoruthenium derivatives 8 and 9. While compound 5 reacts with CO and SO2 by cleavage of one Ru - O bond to yield the 1:1 adducts [RuCl2(L){k(P)-iPr2PCH2CO2Me}{k2(P,O)-iPr2PCH2CO2Me}] (10, 11), the reaction of the dibromo derivative 8 with CO in solution gives the dicarbonyl complex [RuBr2(CO)2{k(P)-iPr2PCH2CO2Me}2](13). If CO is passed over 8 in the solid state, the corresponding monocarbonyl compound 14 is formed. The hydridoruthenium(II) complex 16, which is obtained from equimolar amounts of [RuHCl(CO)(PiPr3)2] (15) and 2, reacts with HC≡CMe by insertion to give the vinyl derivative [RuCl{E - CH=CHMe}(CO)(PiPr3){k2(P,O)-iPr2CH2CO2Me}] (17). Treatment of 5 with HC̊' (R' = H, Me, tBu, Ph) and of 6, 8, 9 with HC≡CPh affords upon photochemical activation the octahedral vinylidene complexes [RuX2-(=C=CHR){k(P)-iPr2PCH2CO2R}{k2(P,O)-iPr2PCH2CO2R}] (18-21 and 23-25) in good to excellent yield. At room temperature, these compounds (with the exception of 25) are highly fluxional in solution. From 31P-NMR measurements, the free energies of activation ΔG
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19951280108
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  • 6
    Electronic Resource
    Electronic Resource
    Stepwise Insertion of Alkylisocyanides into the Metal-Alkyne Bond of Half-Sandwich Type Rhodium Complexes: Synthesis and Structural Characterization of Metallacyclobutenes and MetallacyclopentenesDedicated to Professor Gerhard E. Herberich on the occasion of his 60th birthday. (1996)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 129 (1996), S. 903-910 
    Details
    ISSN: 0009-2940
    Keywords: Rhodium complexes ; Alkyne complexes ; Insertion reactions ; Alkyl isocyanides ; Metallacycles ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The cyclopentadienyl complexes [C5H5Rh(RC≡CR′)(SbiPr3)] (5-8), which were prepared from trans-[RhCl-(RC≡CR′)(SbiPr3)2] (1-4) and NaC5H5 and which contain a labile Rh-SbiPr3 bond, reacted with CO and CNR″ (R″ = Me, tBu) to give the carbonyl and isocyanide derivatives [C5H5Rh(RC≡CR′)(CO)] (9-11) and [C5H5Rh(RC≡CR′)-(CNR″)] (12-16), respectively. On treatment of 12 (R = R′ = Ph; R″ = Me) with SbiPr3, the metallacyclobutene complex [C5H5Rh{κ2(C,C}-C( = NMe)CPh=CPh}(SbiPr3)] (17) was formed; it reacts with excess CNMe or CNtBu to yield the metallacyclopentenes [C5H5Rh{κ2(C,C)-C(=NMe)CPh=CPhC-(=NR)}(CNR)] (18, 19). Similar compounds 20-23 containing a five-membered RhC4 metallacycle were prepared either from [C5H5Rh(RC≡CR′)(SbiPr3)] (7, 8) or [C5H5Rh-(PhC≡CPh)(CNtBu)] (14) and excess isocyanide. The crystal and molecular structures of 17 and 18 (R = Me) have been determined.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19961290805
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  • 7
    Electronic Resource
    Electronic Resource
    A Series of Carbonyl-, Olefin-, Alkyne-, Hydrido-, and Vinyliridium Complexes Containing Bulky Bifunctional Phosphanes iPr2PCH2X as LigandsDedicated to Professor Hans Bürger on the occasion of his 60th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 1591-1603 
    Details
    ISSN: 0009-2940
    Keywords: Iridium ; Hydrido complexes ; Olefin complexes ; C-H activation ; P ligands ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Etheneiridium(I) complexes of the general composition trans-[IrCl(C2H4)L2] [L = iPr2PCH2CO2Me (2a), iPr2PCH2CO2Et (2b), iPr2P(CH2)3NMe2 (2c)] have been prepared either from [IrClL2] (3) or [IrCl(C2H4)2]2 (7) as starting materials. The corresponding carbonyl derivatives trans-[IrCl(CO)L2] (6, 10, 11) are obtained along similar routes. Photolysis of trans-[IrCl(C2H4)L2] (L = 2a, 2b) leads, by intramolecular C-H activation, to the formation of the octahedral hydrido(vinyl)iridium(III) compounds [IrHCl(CH=CH2)(k-L)(k2-L)] (16, 17), which are highly fluctional in solution. Carbonyl(hydrido)(vinyl) complexes are accessible either from 16 or 17 and CO, or from trans-[IrCl(C2H4)L2] (L = 2a) and the propargylic alcohol HC≡CCH(Ph)OH, respectively. Treatment of 3 or the corresponding dihydrido compound [IrH2ClL2] (4) with methyl vinyl ketone or methyl acrylate also yields hydrido(vinyl)iridium(III) complexes [IrHCl(CH=CHX)L2] [X = C(=O)Me (18), C(=O)OMe (19)], in which instead of the C=O function of the phosphanyl ester the carbonyl group of the vinylic moiety is coordinated to the metal. The reaction of 16 (L = 2a) with terminal alkynes HC≡CR (R = Ph, CO2Me) affords the structurally related alkynyl(hydrido)iridium(III) compounds [IrHCl(C≡CR)(k-L)(k2-L)] (28, 29), while from 16 and internal alkynes RC≡CR) the iridium(I) complexes trans-[IrCl1(RC≡CR)L2] (30, 31) are obtained, Stepwise treatment of trans-[IrCl(RC≡CR)L2] (6: L = 2a) with NaN(SiMe3)2, (ii) H2O, and (iii) HCl leads, in the coordination sphere of the metal center, to a conversion of iPr2PCH2CO2Me to iPr2PCH2CO2H via the isolated phosphanylenolate and phosphanylacetate complexes 32 and 33 as intermediates.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971301107
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  • 8
    Electronic Resource
    Electronic Resource
    Über die Oxydation mit Bromamiden und Bromimiden. Reaktionsmechanismus und Methode zur Konformationsanalyse (1962)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 95 (1962), S. 1873-1880 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bei der Oxydation von Alkoholen durch N-Brom-succinimid oder N-Bromacetamid ist elementares Brom das oxydierende Agens; es entsteht in einer autokatalytischen Reaktion. - Die photometrische Verfolgung des Bromgehaltes in der Reaktionslösung ergibt gut auswertbare Extinktions-Zeit-Kurven, wenn die Reaktionen durch definierte Mengen elementaren Broms gestartet werden. In Verbindung mit der Empfindlichkeit optischer Messungen und dem bekannten Reaktionsverlauf (Ablösung eines Hydridions) ergibt sich damit eine Mikromethode zur Konformationsanalyse.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19620950806
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  • 9
    Electronic Resource
    Electronic Resource
    Hydrazin-Reaktionen, IX Cyclisierung von 5-Desoxy-5-[α-methyl-hydrazino]-D-xylose zum Siebenring-Hydrazon (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 475-485 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Hydrazine Reactions, IX Cyclisation of 5-Deoxy-5-(α-methylhydrazino)-D-xylose to a Seven-membered Ring-hydrazoneReaction of methylhydrazine with O-p-tolylsulfonyl sugars results α-methylhydrazino sugars, which can be converted to methylamino sugars by hydrogenation. In this way 5-deoxy-1,2-O-isopropylidene-5-(α-methylhydrazino)-α-D-xylofuranose (2) is synthesised from 1. By ring closure of free 5-deoxy-5-(α-methylhydrazino)-D-xylose in alkaline or neutral solution the seven-membered ring-hydrazone 9 is obtained. Acid hydrolysis of 9 gives under ring contraction a furanose form 5. The seven-membered ring 9 exists in a chair conformation based on n.m.r. data. The mass spectrum of 11 is discussed.
    Notes: Methylhydrazin reagiert mit O-Tosyl-Zuckern zu [α-Methyl-hydrazino]-Zuckern, aus denen durch Hydrierung Methylamino-Zucker zugänglich sind, Aus 1 ist auf diesem Wege 5-Desoxy-1.2-O-isopropyliden-5-[α-methyl-hydrazino]-α-D-xylofuranose (2) erhältlich. Freie 5-Desoxy-5-[α-methyl-hydrazino]-D-xylose cyclisiert in alkalischer bis neutraler Lösung zum Siebenring-Hydrazon 9. In saurer Lösung wird 9 gespalten und bildet unter Ringverengung eine Furanoseform 5 aus. Der Siebenring 9 liegt nach den NMR-Daten in einer Sesselkonformation vor. Das Massenspektrum von 11 wird diskutiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030217
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  • 10
    Electronic Resource
    Electronic Resource
    Investigations on the decomposition of lateral perester groups in maleic anhydride copolymers (1989)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 190 (1989), S. 2325-2328 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The reaction of maleic anhydride (MAn) copolymers with tert-butyl hydroperoxide results in copolymers with lateral perester and carboxyl groups. As these copolymers are of interest as initiators of free-radical polymerization, their decomposition mechanism and their decomposition constants were investigated. Surprisingly, a dependence of the decomposition constants on the comonomer of MAn was found. The interaction of the carboxyl group with the perester group is discussed as an essential reason of the comonomer influence.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1989.021900933
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