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  • 1
    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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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Nickel Hemiporphyrazines as Bisdienes and Bisdienophiles: Synthesis and Characterization (1996)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 129 (1996), S. 237-242 
    Details
    ISSN: 0009-2940
    Keywords: Hemiporphyrazines ; Macrocyclic bisdienes and bisdienophiles ; Nickel complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The bisdienophilic (hemiporphyrazinato)nickel complexes 1a-d bearing various alkoxy groups were synthesized from diiminoisoindoles 9a-d, diaminopyridines 10a, d, and nickel acetate. Reaction of 1a-d with an excess of pentaene 3 delivered the macrocyclic bisdienes 2a-d. The hemiporphyrezines were characterized by 1H- and 13C-NMR spectroscopy. The NMR spectra of the 1,6,16,21-tetrabutoxy-substituted compounds 1b and 2b are discussed with respect to the presence of syn/anti isomers.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19961290220
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    Paper (German National Licenses)
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  • 3
    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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    Paper (German National Licenses)
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