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  • Articles  (37)
  • Organic Chemistry  (31)
  • Diels-Alder reactions  (4)
  • Isocyanide complexes  (2)
  • Wiley-Blackwell  (37)
  • 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
    Synthesis of a Bisdienophilic Phthalocyanine and of Precursors for Repetitive Diels-Alder Reactions Based on Hemiporphyrazines and Phthalocyanines (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 801-806 
    Details
    ISSN: 0009-2940
    Keywords: Unsymmetrical phthalocyanines ; Hemiporphyrazines ; Macrocyclic bisdienes and bisdienophiles ; Diels-Alder reactions ; Ladder polymers ; Cycloaddition ; Macrocycles ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The specific synthesis of a metal-free bisdienophilic phthalocyanine 193, suitable for repetitive Diels-Alder reactions, is reported. This was achieved by condensation of 191,3,3-trichloro-6/7-nitroioindolenine (191) and 4,9-dibutoxy-2,3,5,8-tetrahydro-1,3-diimino-1H-5,8-epoxybenz[f]isoindoline (2). The ability of 3 to undergo Diels-Alder reactions was tested by reaction with an excess of 1,2,3,4-tetraphenylcyclopentadienone (5). Experimental data of the hemiporphyrazines 9, 10, and 11, which can be used as precursors for the synthesis of ladder polymers, are also given in the Experimental Section.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971300620
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  • 3
    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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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis and Electrochemistry of Diels-Alder Adducts of [60] Fullerene with a Phthalocyanine and a Hemiporphyrazine (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 1375-1378 
    Details
    ISSN: 0009-2940
    Keywords: Phthalocyanines ; Hemiporphyrazines ; Fullerenes ; Diels-Alder reactions ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of a new Diels-Alder adduct 7 of [60]fullerene and a phthalocyaninenickel compound containing a longer spacer than the originally reported Diels-Alder adduct 1 is described. The bisenophilic hemiporphyrazinenickel compound 11 reacts with [60]fullerene to form a Diels-Alder adduct 12 containing two fullerene units. Spectroelectrochemical investigations of 7 and 12 reveal multiple reductions, which are attributed to the corresponding subunits of the molecules. In contrast to 1, the election acceptor properties of the [60]fullerene unit in both molecules have no influence on the electronic properties of the phthalocyanine and hemiporphyrazine, respectively.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971301005
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis and Diels-Alder Reactions of Some New (Phthalocyanine)nickel Complexes (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 693-703 
    Details
    ISSN: 1434-1948
    Keywords: (Phthalocyanine)nickel complexes ; Unsymmetrical phthalocyanines ; Isobenzofurans ; Diels-Alder reactions ; Ladder-type molecules ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The octasubstituted (phthalocyanine)nickel complexes 4a,b, soluble in common organic solvents, bearing four dienophilic functionalities were synthesized from the corresponding phthalodinitriles 3a,b and nickel(II) acetate. Reaction of 4a with tetracyclone 5 led to the phthalocyanine-tetracyclone adduct 6 which is a precursor for an intermediate phthalocyanine 7 containing four isobenzofuran moieties. The capability of 7 to react as tetrakis(diene) was demonstrated by its reaction with naphthoquinone. Furthermore, the unsymmetrical phthalocyanines 13 and 16a,b,c containing one dienophilic functionality were synthesized using a statistical approach. Their tetracyclone adducts 17, 18a,b,c can be used for the synthesis of ladder-type phthalocyanine dimers. The dimer 22 was synthesized from 18c and p-benzoquinone via the isobenzofuran intermediate 19 and the benzoquinone adduct 21. For dehydration experiments the naphthoquinone monoadduct 23 was synthesized from 18c. Dehydration of 22 and 23 was carried out successfully with p-toluenesulfonic acid. The Diels-Alder reactions are discussed with respect to the occurring exo/endo ratio.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis of an Oligo(phenylenevinylene)-Bridged Phthalocyanine Dimer (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1687-1691 
    Details
    ISSN: 1434-193X
    Keywords: Nickel phthalocyanines ; Phthalocyanines ; Diels-Alder reactions ; Polymers ; Wittig reactions ; Cycloadditions ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The nickel phthalocyanine 4, which is soluble in common organic solvents, has been synthesized from the corresponding tetracyclone monoadduct 1 and acrolein (3). Reaction of 4 with p-toluenesulfonic acid leads to the modified phthalocyanine monoaldehyde 5. The capability of 5 to undergo a Wittig reaction has been demonstrated with benzyltriphenylphosphonium bromide (6). Furthermore, a dimer 9 has been synthesized by treating 5 with 0.5 equiv. of xylylenebis(triphenylphosphonium bromide) (8). Dimer 9 constitutes a model compound for corresponding PPV polymers containing phthalocyanine subunits.
    Additional Material: 1 Ill.
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  • 7
    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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  • 8
    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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  • 9
    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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  • 10
    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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