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  • 1
    Electronic Resource
    Electronic Resource
    (Tetracyannaphthalocyaninato)eisen(II) mit Isocyaniden als axialen LigandenHerrn Professor Dr. Horst Prinzbach zum 60. Geburtstag gewidmet. (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1243-1247 
    Details
    ISSN: 0009-2940
    Keywords: (Tetracyanonaphthalocyaninato)iron(II) ; Isocyanide complexes ; Semiconductors ; organic ; Iron complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (Tetracyanonaphthalocyaninato)iron(II) with Isocyanides as Axial Ligands(Tetracyanonaphthalocyaninato)iron(II) [(CN)4-2,3-NcFe; 6] is obtained by treating 2,3,6-tricyanonaphthalene (5) with iron(II) acetate. Compound 5 is synthesized according to the route given in Scheme 1. The mononuclear bisaxial isocyanide complexes (CN)4-2,3-NcFeL2 7-9 with L = tBuNC, cHxNC and AdNC as well as the bridged complex [(CN)4-2,3-NcFe(dib)]n (10) are formed as stable compounds by treating 6 with the neat ligands L. The spectroscopic properties of the complexes are described and compared with the analogous compounds (CN)4PcFeL2, 2,3-NcFeL2, 1,2-NcFeL2, and with PcFeL2. The bridged complex [(CN)4-2,3-NcFe(dib)]n (10) exhibits only poor semiconducting properties as compared to [2,3-NcFe(dib)]n. The oligomer 10 can be doped with iodine, and the resulting product [(CN)4-2,3-NcFe(dib)I1.4]n shows a powder conductivity s̰RT = 2 × 10-5 S/cm at room temperature.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250534
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  • 2
    Electronic Resource
    Electronic Resource
    Soluble Substituted μ-Oxo(phthalocyaninato)iron(III) Dimers (1995)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 128 (1995), S. 589-598 
    Details
    ISSN: 0009-2940
    Keywords: μ-Oxobis(phthalocyaninato)iron ; μ-Oxo dimers ; Mössbauer spectroscopy ; Iron complexes ; Phthalocyanines ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Attempts to prepare various peripheral tetra- and octasubstituted (phthalocyaninato)iron derivatives RnPcFe [n = 4: R = CH2OEt (6e), CO2Et (6h), CO2-n-C6H13 (6l), O(2-Et-n-C6H13) (6j), OCH2C(CH3)3 (6k), OCH2C(CH3)2CH2Ph (6l); n = 8: R = CH2CH(CO2Me)CH(CO2Me)CH2 (6f), CH2CH(CO2Et)-CH(CO2Et)CH2 (6g), O-n-C8H17 (6m), O(2-Et-n-C6H13) (6n)] by starting from the corresponding substituted phthalonitriles led to substituted (μ-oxo)bis[(phthalocyaninato)iron(III)] compounds [RnPcFe]2O. The tert-butyl- and ethyl-substituted systems [tBu4PcFe]2O (6c) and [Et4PcFe]2O (6d) were reinve-stigated. UV/Vis, FD mass, Mössbauer, NMR as well as ESR spectroscopy was used to characterize the complexes [RnPcFe]2O to furnish evidence for the presence of Fe-O-Fe moieties in [RnPcFe]2O. The UV/Vis data reported for [RnPcFe]2O as well as their spectral behavior in pyridine correspond to unsubstituted [PcFe]2O. Mössbauer spectra of [RnPcFe]2O show that the complexes were obtained as a mixture of two isomeric μ-oxo compounds A (δFe = 0.22 mm s-1, ΔEQ = 1.33-1.39 mm s-1) and B (ΔFe = 0.33-0.36 mm s-1, ΔEQ = 0.39-0.53 mm s-1), whose Mössbauer parameters are comparable to [PcFe]2O μ-oxo(2) and μ-oxo(1), respectively. Mössbauer spectral data of [RnPcFe]2O indicate high-spin (S = 5/2) FeIII centers. NMR-spectra of [RnPcFe]2O (n = 4: R = tBu, Et, O(2-Et-n-C6H13), OCH2C(CH3)2CH2Ph; n = 8: R = O-n-C8H17, O(2-Et-n-C6H13) give further evidence for μ-oxo bridged structures.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19951280611
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  • 3
    Electronic Resource
    Electronic Resource
    Monomere und überbrückte oligomere (Tetrasulfophthalocyaninato)eisen(II)-Komplexe mit Isocyaniden und N-Donoren als axialen Liganden (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 833-839 
    Details
    ISSN: 0009-2940
    Keywords: Tetrasulfophthalocyaninato ligand ; Iron complexes ; Isocyanide ligands ; Mößbauer spectroscopy, 57Fe ; Semiconductors, organic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Monomeric and Bridged Oligomeric (Tetrasulfophthalocyaninato)iron(II) Complexes with Isocyanides and N-Donors as Axial Ligands(Tetrasulfophthalocyaninato)iron(II) (TsPcFe) (1) is treated with the isocyanides tert-butyl isocyanide (tBuNC), 1,4-diisocyanobenzene (dib), 2,3,5,6-tetramethyl-1,4-diisocyanobenzene (me4dib), and 4-isocyano-3,5-dimethylpyridine (me2pyNC), and also with pyrazine (pyz) leading to bisaxially coordinated monomers TsPcFe(L)2 (L=tBuNC, dib, me4dib) and the bridged oligomers [TsPcFe(L)]n (L=dib, me4dib, me2pyNC, and pyz). All these complexes are soluble in methanol or water. The spectroscopic properties of the complexes are described, and the average chain lengths of the bridged oligomers are determined by 1H-NMR spectroscopy. The bridged stacked systems exhibit semiconducting properties with and without iodine doping.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240425
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  • 4
    Electronic Resource
    Electronic Resource
    Bisaxial koordinierte (Tetraphenylporphinato)eisen(II)-Komplexe (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 841-847 
    Details
    ISSN: 0009-2940
    Keywords: Tetraphenylporphinato ligand ; Iron complexes ; Mößbauer spectroscopy ; 57Fe / Semiconductors, organic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bisaxially Coordinated (Tetraphenylporphinato)iron(II) ComplexesThe coordination behavior of (tetraphenylporphinato)iron(II) (TPPFe) has been studied with the preparation of the monomeric complexes TPPFe(L)2 with L=py (pyridine), pyz (pyrazine), 2,6-dimepyz (2,6-dimethylpyrazine), bpy (4,4′-bipyridine), bpyac [1,2-bis(4-pyridyl)acetylene], dabco (1,4-diazabicyclo [2.2.2]octane), and BzINC (benzyl isocyanide). Pure TPPFe has been obtained by thermal decomposition of TPPFe(py)2. The monomeric complexes TPPFe(L)2 with L=pyz, bpy, bpyac, and dabco can be transformed into the bridged systems [TPPFe(L)]n by heating them in toluene or chlorobenzene. The bridged structure of the complexes [TPPFe(L)]n has been confirmed by IR and TG/DTA investigations and especially by Mößbauer spectroscopy. In comparison with the corresponding (phthalocyaninato)iron compounds the bridged TPPFe complexes exhibit lower semi conducting properties even after doping with iodine.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240426
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  • 5
    Electronic Resource
    Electronic Resource
    Generation of vinyl cations by nitrosation of N-silylated imines and enaminesPresented as a poster at the 10th IUPAC Conference on Physical Organic Chemistry at Technion, Haifa, Israel, August 5-10, 1990. (1993)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 6 (1993), S. 44-46 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The reaction of monosilylated imines and a disilylated enamine with nitrosyl salts in dichloromethane at -78°C is shown to proceed via intermediate vinyl diazonium salts and vinyl cations.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610060107
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  • 6
    Electronic Resource
    Electronic Resource
    The search for the ethynylcation: Nitrosation of N,N-bis(trimethylsilyl)ynamines (1995)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 8 (1995), S. 191-194 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The reaction of bis-silylated ynamines with different nitrosyl reagents affords products derived from an electrophilic attack at the β-carbon atom and not the expected alkynyldiazonium salts.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610080310
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  • 7
    Electronic Resource
    Electronic Resource
    Umsetzung von Allyl(nonafluorbutyl)sulfonen mit Michael-Akzeptoren, Synthese von Chrysanthemumsäurederivaten (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 853-858 
    Details
    ISSN: 0170-2041
    Keywords: Sulfones, allyl nonafluorobutyl ; Chrysanthemic acid ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reaction of Allyl Nonafluorobutyl Sulfones with Michael Acceptors, Synthesis of Chrysanthemic Acid Derivatives3-Methyl-2-butenyl nonafluorobutyl sulfone (4) reacts with ethyl 3-methyl-2-butenoate (ethyl senecioate, 2) to form ethyl chrysanthemate (3) 5-Methyl-1-(2-methyl-1-propenyl)-3-pentenyl nonafluorobutyl sulfone (5) is formed as a byproduct. The nonaflone 4 is prepared by reaction of 3-methyl-2-butenyl bromide (9) with sodium nonafluorobutanesulfinate or by treating isoprene with nonafluorobutanesulfinic acid. Reaction of 3,3-dichloro-2-propenyl nonafluorobutyl sulfone (12) with ethyl senecioate (2) does not lead to ethyl permethrinate (13), instead self-condensation products of 12, the cyclopropyl sulfone 15 and the disulfone 16 are obtained.
    Notes: (3-Methyl-2-butenyl)nonafluorbutyl)sulfon (4) reagiert mit 3-Methyl-2-butensäure-ethylester (2) (Seneciosäure-ethylester) unter Bildung von Chrysanthemumsäure-ethylester (3). Als Nebenprodukt wird [5-Methyl-1-(2-methyl-1-propenyl)-3-pentenyl]-[nonafluorbutyl)sulfon (5) erhalten. Das Nonaflon 4 ist durch Umsetzung von 3-Methyl-2-butenylbromid (9) mit Natriumnonafluorbutansulfinat oder durch Umsetzung von Isopren mit Nonafluorbutansulfinsäure zugänglich. (3,3-Dichlor-2-propenyl)(nonafluorbutyl)sulfon (12) reagiert mit Seneciosäure-ethylester (2) nicht unter Bildung von Permethrinsäure-ethylester (13), sondern unter Selbstkondensation zu dem Cyclopropylsulfon 15 und dem Disulfon 16.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890236
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  • 8
    Electronic Resource
    Electronic Resource
    Alkoholyse von Toluolsulfonsäureestern IV.III. Mitteilung: voranstehend. Die Solvolyse Der Toluolsulfonate Der Beiden cis-α-Hydrindanole Eine als Abspaltungsreaktion verlaufende Solvolyse in Alkohol (1957)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 610 (1957), S. 106-115 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Die Bildungsbedingungen der beiden isomeren cis-α-Hydrindanole I und II werden studiert; die Konfiguration der Isomeren ergibt sich im Sinne der bisherigen Zuordnung  -  I = 1c 8c 9c und II = 1t 8c 9c  -  aus den Solvolysegeschwindigkeiten ihrer Toluolsulfonate. Für II ergibt sich eine Konstante, die nahe bei der des trans-o-Methylcyclopentanols liegt. Für I läßt sich wie für das cis-o-Methylcyclopentanol keine Konstante 1. Ordnung errechnen; die Geschwindigkeits-Intervall-„Konstante“ nimmt während der Reaktion ab. Eine Umlagerung I → II erfolgt dabei nicht. Als Reaktionsprodukt entsteht aus I wie aus II nur Hexahydroinden; für den aus I entstehenden Kohlenwasserstoff wurde die Δ1,2-Lage der Doppelbindung  -  Abspaltung im Sinne der HOFMANNschen Regel  -  erwiesen.  -  Eine verbesserte, potentiometrische Methode zur Ermittlung der Geschwindigkeitskonstanten wird mitgeteilt.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19576100110
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  • 9
    Electronic Resource
    Electronic Resource
    Synthese von bis(trifluormethyl)substituierten Pyrethroiden (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 833-845 
    Details
    ISSN: 0170-2041
    Keywords: Pyrethroids ; Olefins, bis(trifluoromethyl)-substituted ; Caronaldehydic acid ethyl ester, hexafluoro- ; Fenvalerate, hexafluoro- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Bis(trifluoromethyl)-Substituted PyrethroidsA method for the preparation of 1,1-bis(trifluoromethyl)-substituted pyrethroids is described. For this purpose, 1,1-bis(trifluoromethyl)-substituted olefins 9 are prepared by an easy method from the aldehydes 17 with 2,2-dichlorohexafluoropropane (16) and triphenylphosphine and converted into 2,2-bis(trifluoromethyl)cyclopropanecarboxylates 5a, g, h, i by reacting with (ethoxy-carbonylmethylene)dimethylsulfurane (10). Ethyl 3-formyl-2,2-bis(trifluoromethyl)cyclopropanecarboxylate (hexafluorocaronaldehydic acid ethyl ester) (5c) is obtained from 4,4,4-trifluoro-3-(trifluoromethyl)-2-butenal diethyl acetal (9c) and the sulfurane 10. Compound 5c is an important intermediate in the preparation of the bis(trifluoromethyl)-substituted pyrethroid esters 5d-f. The hydrolysis of the esters 5a, h affords the corresponding carboxylic acids 6a, b which are converted into the pyrethroid esters 7a, b via the acyl chlorides 38 by treating with α-cyano-3-phen-oxybenzyl alcohol (39). 1-(4-Chlorophenyl)-3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (9g) reacts with acetone cyanohydrin to the nitrile 47. The acyl chloride 49 obtained from the nitrile 47 via the carboxylic acid 48 is treated with α-cyano-3-phenoxybenzyl alcohol (39) to form hexafluorofenvalerate (8).
    Notes: Es wird über eine Methode zur Darstellung von 1,1-bis(trifluor-methyl)substituierten Pyrethroiden berichtet. Dazu werden 1,1-bis(trifluormethyl)substituierte Olefine 9 auf einfache Weise durch Reaktion der Aldehyde 17 mit 2,2-Dichlorhexafluorpropan (16) und Triphenylphosphan dargestellt und mit (Ethoxycarbonylmethylen)dimethylsulfuran (10) in die 2,2-Bis(trifluormethyl)cyclo-propancarbonsäureester (5a, g, h, i) übergeführt. Ausgehend von 4,4,4-Trifluor-3-(trifluormethyl)-2-butenal-diethylacetal (9c) wird durch Umsetzung mit dem Sulfuran 10 der 3-Formyl-2,2-bis(trifluormethyl)cyclopropancarbonsäure-ethylester (Hexafluorcaronaldehydsäure-ethylester) (5c) erhalten. 5c stellt eine wichtige Zwischenstufe zur Darstellung der bis(trifluormethyl)substituierten Pyrethroidester 5d-f dar. Die Hydrolyse der Esterfunktion in den Pyrethroidestern 5a, h liefert die Carbonsäuren 6a, b, die über die Säurechloride 38 und Umsetzung mit α-Cyan-3-phenoxy-benzylalkohol (39) in die entsprechenden Pyrethroidester 7a, b übergeführt werden. 1-(4-Chlorphenyl)-3,3,3-trifluor-2-(trifluor-methyl)-1-propen (9g) reagiert mit Aceton-cyanhydrin zum Nitril 47. Nach Überführung in die Carbonsäure 48 und das Säurechlorid 49 wird dieses mit α-Cyan-3-phenoxybenzylalkohol (39) zum Hexafluorfenvalerat (8) umgesetzt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890234
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  • 10
    Electronic Resource
    Electronic Resource
    Die Kristallstruktur eines bisaxial mit tert-Butylacetylen substituierter GermaniumhemiporphyrazinsHerrn Professor Harry Hahn zum 65. Geburtstag gewidmet. (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1946-1951 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Crystal Structure of a Bisaxial with tert-Butylacetylene Substituted Germanium Hemiporphyracinetrans-Bis(3,3-dimethyl-1-butyneyl) hemiporphyracine germanium crystallizes by sublimin furane in triclinic crystals with the space group P1 and the lattice constants a = 860.4, b = 960.7, c = 1141.6 pm; α = 74.01, β = 113.62, γ = 108.50°. The unit cell contains one centrosymmetric molecule, in which the germanium atom is surrounded in a distorted octahedral coordination by four nitrogen atoms of the hemiporphyracine ligand (Ge - N: 195.6 and 217.2 pm) and two carbon atoms of the tert-butylacetylene group (Ge - C: 193.8 pm). The germanium hemiporphyracine moiety is mostly planar.
    Notes: trans-Bis(3,3-dimethyl-1-butinyl)hemiporphyrazin-germanium kristallisiert beim Sublimieren in triklinen Kristallen, mit der Raumgruppe P1 und den Gitterkonstanten a = 860.4, b = 960.7, c = 1141.6 pm; α = 74.01, β = 113.62, γ = 108.50°. Die Elementarzelle enthält ein zentrosymmetrisches Molekül, in dem das Germaniumatom verzerrt oktaedrisch von 4 Stickstoffatomen des Hemiporphyrazinliganden (Ge - N: 195.6 und 217.2 pm) und 2 Kohlenstoffatomen der tert-Butylacetylengruppen (Ge - C: 193.8 pm) umgeben ist. Der Germaniumhemiporphyrazin-Teil ist weitgehend eben gebaut.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019801204
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