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  • 1
    Electronic Resource
    Electronic Resource
    9,10-Phenanthrenocyaninatoeisen(II) (PhcFe) und axial koordinierte Isocyanid-Komplexe (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 1105-1110 
    Details
    ISSN: 0009-2940
    Keywords: 9,10-Phenanthrenocyaninatoiron(II) ; Isocyanide complexes ; Porphyrin derivatives ; Semiconductors, organic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 9,10-Phenanthrenocyaninatoiron(II) (PhcFe) and Axially Coordinated Isocyanide Complexes9,10-Phenanthrenocyaninatoiron(II) (PhcFe) is synthesized from 9,10-dicyanophenanthrene (3) and pentacarbonyliron. PhcFe exhibits similar spectroscopic properties (UV/VIS and Mößbauer spectra) and similar oxidation potentials as 1,2-Naphthalocyaninatoiron(II) (1,2-NcFe) and Phthalocyaninatoiron(II) (PcFe). Isocyanides RNC (R = tBu, cHx, Bzl, Me2Ph) react with PhcFe to form the corresponding bisaxially substituted 9,10-phenanthrenocyaninatoiron(II) compounds 4-7. Reaction of PhcFe with 1,4-diisocyanobenzene (dib) yields the bridged complex [PhcFe(dib)]n.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230525
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  • 2
    Electronic Resource
    Electronic Resource
    Lösliche (Tetraethylphthalocyaninato)eisen(II)- und -cobalt(II)-Verbindungen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 2315-2321 
    Details
    ISSN: 0009-2940
    Keywords: Tetraethylphthalocyanine, metal complexes of ; Isocyanide complexes, bridged ; Porphyrines ; Semiconductors, organic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Soluble (Tetraethylphthalocyaninato)iron(II) and -cobalt(II) CompoundsThe (tetraethylphthalocyaninato)iron and -cobalt compounds Et4PcFe (9), Et4PcCo (8), and Et4PcH2 (7) have been synthesized starting from 3,4-dibromoacetophenone (1) via the corresponding dinitrile 5 or isoindolenine 6, respectively. Et4PcFe (9) reacts with tBuNC, p-diisocyanobenzene (dib), and me4dib to form the bisaxially coordinated compound Et4PcFe(tBuNc)2 (10) and the oligomers [Et4PcFe(dib)]n (11) and [Et4PcFe- (me4dib)]n (12). All of the synthesized compounds, except the oligomers with a chain length of more than 8 - 14 units, are soluble in organic solvents such as chloroform or toluene. The new compounds were characterized by 1H-, 13C-NMR, 13C-CP/NMR, UV/Vis, and IR spectra. In addition the redox properties of Et4PcCo (8) were studied by cyclic voltammetry and spectroelectrochemical methods. The Mößbauer spectra of the (phthalocyaninato)iron compounds 9, 11, and 12 demonstrate the bridged structure of [Et4PcFe(L)]n (L = dib, me4dib) (11, 12). The powder conductivity of [Et4PcFe(dib)]n (11) (σRT = 5·10-6 S/cm) is ca. 106 times higher than that of Et4PcFe (9) (σRT = 9·10-12 S/cm). After doping with iodine the oligomers 11 and 12 show an increase in conductivity of 105 and 104, respectively (σRT ≍ 10-2 S/cm for [Et4PcFe(dib)I0.85]n).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911241026
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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
    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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  • 5
    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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  • 6
    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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  • 7
    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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  • 8
    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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  • 9
    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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  • 10
    Electronic Resource
    Electronic Resource
    Synthese und Struktur von Cyano(dihydrodibenzo[b,i]-[1,4,8,11]tetraazacyclotetradecinato)cobalt(III) (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1791-1797 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Structure of Cyano(dihydrodibenzo[b,i][1,4,8,11]tetraazacyclotetradecinato)-cobalt(III)Cyano(dihydrodibenzo[b,i][1,4,8,11]tetraazacyclotetradecinato)cobalt(III) (CotaaCN) is formed by reaction of Cotaa with sodium cyanide and oxygen. CotaaCN crystallizes orthorhombic, space group P212121 with the cell dimensions a = 698.6 pm, b = 1466.2 pm, and c = 1553.7 pm, Z = 4. The compound is a pentacoordinated monomer with a Co—C distance of 182 pm. The IR spectrum of this monomeric compound exhibits a CN-valence frequency at 2116 cm-1.
    Notes: Cyano(dihydrodibenzo[b,i][1,4,8,11]tetraazacyclotetradecinato)cobalt(III) (CotaaCN) wird durch Umsetzung von Cotaa mit NaCN und Sauerstoff dargestellt. CotaaCN kristallisiert orthorhombisch in der Raumgruppe P212121 mit den Gitterkonstanten a = 698.6 pm, b = 1466.2 pm und c = 1553.7 pm, Z = 4. Die Verbindung liegt als pentakoordiniertes Monomer vor. Der Co—C-Abstand beträgt 182 pm. Die CN-Valenzschwingung im IR-Spektrum dieser monomeren Verbindung liegt bei 2116 cm-1.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419841105
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