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  • 1
    Electronic Resource
    Electronic Resource
    Vinylkationen, 26: Synthese und Solvolyse von Vinylfluoriden (1978)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 111 (1978), S. 1253-1263 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Vinyl Cations, 26: Syntheses and Solvolyses of Vinyl FluoridesThe vinyl fluorides 5-8 were prepared by treatment of the corresponding olefins with BrF and subsequent dehydrobromination. The solvolysis reactions in various solvents were studied. The products and their rates of solvolysis measured under different conditions point to a vinyl cation mechanism of the solvolysis reactions.
    Notes: Die Vinylfluoride 5-8 wurden durch Umsetzung der entsprechenden Olefine mit BrF und sich anschließende Dehydrobromierung dargestellt und die Solvolysereaktionen in mehreren Lösungsmitteln untersucht. Die Reaktionsprodukte sowie die unter verschiedenen Bedingungen gemessenen Solvolysegeschwindigkeiten deuten auf einen Verlauf der Solvolyse über Vinylkationen.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19781110405
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  • 2
    Electronic Resource
    Electronic Resource
    Vinyl-Kationen, 20. Synthese und Solvolyse von Bicyclo[5.3.0]dec-1-en-2-yl-triflat (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 2212-2218 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Vinyl Cations, 20. Synthesis and Solvolysis of Bicyclo[5.3.0]dec-l-ene-2-yl TriflateBicyclo[5.3.0]dec-1-ene-2-yl triflate (6) and Δ1(8a)-octalinyl triflate (7) were synthesized and the solvolyses of both compounds were investigated in different solvents. 6 reacts in 50% aqueous ethanol and in 70% trifluoroethanol mostly with rearrangement to 1-decalone (3). Similarly, a rearrangement to the octalinyl system occurs in absol. TFE, in which the enol ether 11 is formed. In contrast, 7 solvolyses in the same solvents mostly with retention of structure. A rearrangement to the bicyclo[5.3.0]decane system was observed only in small amounts. - The triflate 6 solvolyses in 50% aqueous ethanol 343 times faster than 7. The product analyses as well as the kinetics show that the solvolyses occur via vinyl cation intermediates. The octalinyl cation 2 would appear to have a higher stability than the bicyclic vinyl cation 4.
    Notes: Bicyclo[5.3.0]dec-1-en-2-yl-triflat (6) und Δ1(8a)-Octalin-1-yl-triflat (7) wurden synthetisiert und ihre Solvolysereaktionen in verschiedenen Lösungsmitteln untersucht. 6 reagiert in 50proz. wäßr. Äthanol und in 70proz. Trifluoräthanol weitgehend unter Umlagerung zum 1-Decalon (3). In absol. Trifluoräthanol tritt ebenfalls Umlagerung in das Octalinylsystem ein, wobei der Enoläther 11 erhalten wird. 7 solvolysiert in den gleichen Lösungsmitteln weitgehend unter Strukturerhaltung, eine Umlagerung in das Bicyclo[5.3.0]decan-System wird nur in untergeordnetem Maße beobachtet. - Das Triflat 6 solvolysiert in 50proz. wäßr. Äthanol 343 mal schneller als 7. - Die Produktanalysen sowie die Kinetik zeigen, daß die Solvolysen über Vinyl-Kationen ablaufen, wobei das Octalinyl-Kation 2 sich durch eine höhere Stabilität gegenüber dem bicyclischen Vinyl-Kation 4 auszeichnet.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751080707
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  • 3
    Electronic Resource
    Electronic Resource
    Vinylkationen, 24. Eine [1,2]-Hydridwanderung bei der Solvolyse von Phenylvinyl-trifluormethansulfonaten (1977)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 110 (1977), S. 199-207 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Vinyl Cations, 24. A [1,2]-Hydride Shift in the Solvolysis of Phenylvinyl Trifluoromethanesulfonates(E)- and (Z)-1-methyl-2-phenylvinyl trifluoromethanesulfonate (3E, 3Z) and 1-benzylvinyl trifluoromethanesulfonate (4) have been synthesized. Their products of solvolysis were identified and their rates of solvolysis determined in various 2,2,2-trifluoroethanol/water mixtures. Solvolysis of 3E and 3Z leads, besides other products, to ethyl phenyl ketone (9), demonstrating a [1,2]-hydride shift across the double bond in the initially formed vinyl cation 10. In the solvolysis of 4, a [1,2]-hydride shift towards the double bond has not been found.
    Notes: (E)- und (Z)-1-Methyl-2-phenylvinyl-trifluormethansulfonat (3E, 3Z) und 1-Benzylvinyl-trifluormethansulfonat (4) wurden dargestellt, ihre Solvolyseprodukte aufgeklärt und die Solvolyse-geschwindigkeiten in verschiedenen 2,2,2-Trifluorethanol/Wasser-Gemischen bestimmt. Bei der Solvolyse von 3E und 3Z entstand neben anderen Produkten Ethylphenylketon (9), wodurch im zunächst entstehenden Vinylkation 10 eine [1,2]-Hydridwanderung über die Doppelbindung hinweg nachgewiesen wurde. Eine [1,2]-Hydridverschiebung in Richtung auf die Doppelbindung konnte bei der Solvolyse von 4 nicht gefunden werden.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19771100119
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  • 4
    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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  • 5
    Electronic Resource
    Electronic Resource
    Lösliche bisaxial substituierte (Phthalocyaninato)ruthenium-Komplexe (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1733-1738 
    Details
    ISSN: 0009-2940
    Keywords: Phthalocyanine ; Ruthenium complexes ; Pyridines ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Soluble Bisaxially Substituted (Phthalocyaninato)ruthenium ComplexesSeveral attempts to prepare (tBu4Pc)Ru only led to an impure product (tBu4Pc)RuLx. This reacts quantitatively with pyridine to form (tBu4Pc)Ru(py)2, easily purified by chromatography. In addition the preparation of (tBu4Pc)RuL2 with L = pyridine, 2-picoline (2-pic), 3-picoline (3-pic), 4-picoline (4-pic), 2,5-lutidine (2,5-lut), and 2,6-lutidine (2,6-lut), respectively, is described. All complexes are characterized by spectroscopic methods including 1H-NMR spectroscopy. Not even in the cases of (tBu4Pc)RuL2 with L = 2-pic and 2,5-lut, a careful removal of the ligands L by thermogravimetric methods (TG/DTA) leads to pure (tBu4Pc)Ru. For comparison, the bisadducts PcRuL2 with L = pyridine, picolines (2-pic, 3-pic, 4-pic), lutidines (2,3-lut, 2,5-lut, 2,6-lut), and chloropyridines (2-Clpy and 3-Clpy), respectively, are prepared by treatment of PcRu with an excess of the ligand. For the first time (phthalocyaninato)iron complexes PcFeL2 with sterically hindered axial ligands, e.g. PcFe(2-pic)2, are prepared and characterized by 57Fe Mößbauer spectroscopy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240811
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis, Separation and Characterization of Unsymmetrically Substituted PhthalocyaninesDedicated to Professor E. Lindner on the occasion of his 60th birthday. (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 2051-2057 
    Details
    ISSN: 0009-2940
    Keywords: Phthalocyanines, unsymmetrically substituted, chromatographic separation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Unsymmetrically substituted (phthalocyaninato)nickel(II) complexes -7 were synthesized by statistical condensation of 4,5-dipentoxy- (2a), 4,5-diheptyl- (2b), 3,6-dihexoxy- (2c), and 3,6-diheptylphthalonitrile (2d) with 3,4,5,6-tetraphenylphthalonitrile (1) and separated by column chromatography. The obtained phthalocyanines 3-7 were characterized by UV-, IR-, and 1H-NMR spectroscopy.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941271030
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  • 7
    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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  • 8
    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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  • 9
    Electronic Resource
    Electronic Resource
    Soluble (Phthalocyaninato)ruthenium(II) Phosphane Complexes (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 2565-2566 
    Details
    ISSN: 0009-2940
    Keywords: Phthalocyaninato complexes ; Ruthenium complexes ; Phosphanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Hitherto unknown ruthenium phthalocyanine complexes with phosphane ligands - PcRu(PEt2Ph)2 (1) and PcRu(PPh3)2 (2) - soluble in common organic solvents were prepared. Two methods were used for their synthesis: 1) Reaction of phthalonitrile with [Ru2Cl3(PEt2Ph)6]Cl in n-pentanol in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 2) reaction of PcRu with the corresponding phosphanes. The products 1 and 2 were characterized by their IR, UV/Vis, FD-MS, and 1H-NMR data.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931261136
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis of μ-Cyano(2,3-naphthalocyaninato)iron(III) and Comparison to μ-Cyano(phthalocyaninato)iron(III) (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 2559-2563 
    Details
    ISSN: 0009-2940
    Keywords: μ-Cyano(2,3-naphthalocyaninato)iron(III) ; Potassium dicyano(2,3-naphthalocyaninato)ferrate(III) ; Dichloro(2,3-naphthalocyaninato)iron(III) ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Potassium dicyano(2,3-naphthalocyaninato)ferrate(III), K[2,3-NcFe(CN)2] (2), reacts in water with elimination of KCN to form μ-cyano(2,3-naphthalocyaninato)iron(III), [2,3-NcFe(CN)]n (4a). Dichloro(2,3-naphthalocyaninato)iron(III), 2,3-NcFeCl2 (3), reacts with KCN to yield also [2,3-NcFe(CN)]n (4b). Both compounds 4a and 4b show similar IR spectra with a typical blue-shifted CN valence frequency caused by a bridging function of CN-. Compounds 4a and 4b also show almost identical 57Fe-Mössbauer spectra which, however, might be interpreted with a Fe(+II) oxidation state of the iron. The measured magnetic moment of 4 however clearly proves the expected oxidation state +III of the iron in [2,3-NcFe(CN)]n (4). Compounds 4a and 4b both exhibit good semiconducting properties (σRT ∼ 10-3 S/cm) without additional external oxidative doping. The property is quite similar to that of the known μ-cyano(phthalocyaninato)iron [PcFe(CN)]n (σRT ∼ 10-2 S/cm).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931261135
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