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  • Chemistry  (174)
  • Diels-Alder reactions  (4)
  • Olefins, bis(trifluoromethyl)-substituted  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Fragmentation of vinyl triflates by electron impact. Mechanism of an unusual double hydrogen atom transfer reaction (1994)
    New York, NY : Wiley-Blackwell
    Rapid Communications in Mass Spectrometry 8 (1994), S. 427-431 
    Details
    ISSN: 0951-4198
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Physics
    Notes: The main fragmentation pathway of vinyl triflates in mass spectra involves the loss of CF3SO2·, followed by the loss of olefin and/or CO. The loss of TfOH takes place with fragmentation of a vinylic C—H bond. TfOH2+ ions are formed via regiospecific double hydrogen transfer from five- and six-membered cyclic triflates.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/rcm.1290080517
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis, Separation and Characterization of the Structural Isomers of Octa-tert-Butylphthalocyanines and Dienophilic Phthalocyanine Derivatives (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1042-1051 
    Details
    ISSN: 0947-6539
    Keywords: dienophiles ; isomer separation ; macrocyclic ligands ; monomers ; phthalocyanines ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Octa-tert-butylphthalocyanina-tonickel(II) (4) was synthesized from 3,5-di-tert-butylphthalonitrile (1) and nickel acetate. A nonstatistical mixture of the four structural isomers 4a-d was obtained. The isolation of the structural isomers 4a-d by preparative HPLC (MPLC) allowed their unequivocal identification and characterization by spectroscopic techniques. Moreover, a new family of tert-butyl-substituted phthalocya-nines 6-10 containing dienophilic functionalities were prepared by condensation of 3,5-di-tert-butylphthalonitrile (1) with 6,7-dicyano-1,4-epoxy-1,4-dihydronaphthalene (5). The separation of the phthalocyanines 6-10 and of some of their structural isomers was accomplished by normal column chromatography. The structural isomers were characterized by spectroscopic methods in terms of their symmetry.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030710
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Studies on Phosphorus Phthalocyanines and Triazatetrabenzcorroles (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 2759-2767 
    Details
    ISSN: 1434-193X
    Keywords: Phosphorus phthalocyanines ; Triazatetrabenzcorroles ; Dihydroxyphosphorus(V) phthalocyanine hydroxides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The previously reported reaction of phthalocyanines [H2(pc)] with PBr3, which was claimed to give a phosphorus(III) phthalocyanine “(PcPIII)”, has been reinvestigated in detail with both unsubstituted and alkyl-substituted phthalocyanines, 1-4. The products exhibit unusual electronic and mass spectra compared to normal phthalocyanines and have been identified as oxophosphorus(V) triazatetrabenzcorroles 5-8. The corresponding dihydroxyphosphorus(V) phthalocyanine hydroxides 9-12 have also been synthesized for the first time by insertion of phosphorus(V) into phthalocyanines and have been characterized in detail. The different reactivities of PBr3 and POX3 (X = Cl, Br) toward phthalocyanines are discussed.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of Novel Functionalised Zinc Phthalocyanines Applicable in Photodynamic Therapy (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 3441-3453 
    Details
    ISSN: 1434-193X
    Keywords: Zinc phthalocyanines ; Tetra- and octa(carboxyalkyl)phthalocyaninatozinc compounds ; Water soluble ; Photodynamic therapy ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of several new phthalonitriles 3, 9, 14, 25, 33, and 36, functionalised with carboxyl groups, including two examples of amino acid derivatives is described. All new phthalonitriles were converted into their corresponding phthalocyaninatozinc compounds. The phthalocyanines, 2,3,9,10,16,17,23,24-octa(1-carboxyethyloxy)phthalocyaninatozinc (5), 2,9,16,23-tetra(2-amino-2-carboxyethyl)phthalocyaninatozinc (11), 2,9,16,23-tetra(1-carboxy-2-hydroxyethylaminocarbonyl)phthalocyaninatozinc (16), 1,8,15,22-tetra(carboxybutyl)phthalocyaninatozinc (27), 2,3,9,10,16,17,23,24-octa(carboxyalkyl)phthalocyaninatozinc (39), and the nonidentically substituted 9,10,16,17,23,24-hexa(carboxyalkyl)-2-[4-(N-succinimidyloxycarbonyl)butyl]phthaloyaninatozinc (41) are all sufficiently soluble in water. The nonidentically-substituted compounds are important due to their selective binding to tumor-selective antibodies. UV/Vis-spectroscopy was used to investigate the effect of more or less sterically-demanding substituents in the periphery of the phthalocyanines towards aggregation. The phototoxicity towards cancer cells of some of the new compounds was investigated in several in-vitro experiments.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis and Investigations on Nitrido(phthalocyaninato)rhenium Complexes (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 1309-1313 
    Details
    ISSN: 1434-1948
    Keywords: Phthalocyanines ; Rhenium ; Nitrido(octa-n-alkylphthalocyaninato)rhenium compounds ; Nucleophilic additions ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reactions of nitrido(tetra-tert-butylphthalocyaninato)rhenium (1) with boron tribromide leading to (tBu4Pc)ReNBBr3 (4) and with acetone to give the imido complex (tBu4Pc)Re[NC(CH3)2CH2C(O)CH3]OH (2b) and its μ-oxo dimer 3 are reported. Starting from the corresponding 4,5-di-n-alkylphthalonitriles and ammonium perrhenate four soluble nitrido(octa-n-alkylphthalocyaninato)rhenium complexes 5-8 were synthesized. Nitrido(octa-n-pentylphthalocyaninato)rhenium (6) was treated with boron tribromide to afford [(C5H11)8Pc]ReNBBr3 (9).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Novel Nitrido- and Oxo(phthalocyaninato) Complexes of Molybdenum, Tungsten and Rhenium (2000)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 2000 (2000), S. 1025-1030 
    Details
    ISSN: 1434-1948
    Keywords: Phthalocyanines ; Nitrides ; Oxo complexes ; Rhenium ; Molybdenum ; Tungsten ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of new nitrido(phthalocyaninato)molybdenum (1-4) and -tungsten complexes (5-7) starting from the corresponding phthalonitriles and MNCl3 (M = Mo, W) is reported. In addition, the reaction of (tBu4Pc)WN (6) with PPh3 leading, after several steps, to the diamagnetic compound (tBu4Pc)WO (7) is described. The reaction of (tBu4Pc)ReN (9) with PPh3 leads to [(tBu4Pc)ReO]2 (12), and of [(C5H11)8Pc]ReN (10) with PPh3 leads, under different conditions, to {[(C5H11)8Pc]ReO}2O (11).
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of Ladder-Type Oligomers Incorporating Phthalocyanine Units (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 303-311 
    Details
    ISSN: 1434-193X
    Keywords: Phthalocyanines ; Cycloadditions ; Ladder Oligomers ; Macrocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The condensation of substituted diiminoisoindolines with alkyl-substituted 1,3,3-trichloroisoindolines results in the formation of the highly soluble metal-free phthalocyanines 9, 15. By the same methodology, metal-containing phthalocyanines such as 16, 18 are accessible from suitable metal salts. The precursors 24 and26 were obtained from the phthalocyanine 9 and tetracyclone. The generation of the phthalocyanines 23 and 25 possessing isobenzofuran moieties as diene subunits was accomplished; in the presence of excess 28, the tetracyclone-bisadducts 22 and 24 were transformed into the model compounds 29 and 30, while an excess of 20 or 9 leads to the appropriate trimer-oligomers 31 and 32.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    Oligo-2,6-naphthylenevinylenes - New Building Blocks for the Preparation of Photoluminescent Polymeric Materials (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 643-651 
    Details
    ISSN: 1434-193X
    Keywords: Oligomers ; Synthesis design ; Substituent effects ; Luminescence ; Cyclic voltammetry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Synthetic strategies towards appropriate symmetric and unsymmetric functionalization of the naphthalene ring are presented. By means of Knoevenagel and Wittig condensation reactions new fluorescent, differently functionalized oligo(2,6-naphthylenevinylene)s have been synthesized, the presence of terminal aldehyde or bromine substitution opening the way to the incorporation of the fluorescent trimers in a variety of polymeric materials. The effect of substituting the phenylene ring by the more bulky dialkoxynaphthalene system in arylenevinylene-type materials is studied from the structural point of view and the possibility to tune the emission color and the electron affinity through the introduction of naphthylenevinylene and cyano-substituted naphthylenevinylene units is also investigated.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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  • 9
    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.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    Soluble Chloro- and Aryl(phthalocyaninato)indium(III) Complexes: Synthesis and Characterization (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 367-373 
    Details
    ISSN: 1434-1948
    Keywords: Phthalocyanines ; Indium ; Indium-carbon bond ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of highly soluble chloro(phthalocyaninato)indium(III) complexes RxPcInCl (3a: R1 = tert-butyl, R2 = H, x = 4 and 4a: R1 = R2 = n-pentyl, x = 8), and their reactions with R′MgBr [R′ = p-trifluoromethylphenyl- (b), m-trifluoromethylphenyl- (c), p-fluorophenyl- (d), perfluorophenyl- (e)] leading to the stable σ-bonded aryl(phthalocyaninato)indium(III) complexes 3b-e, 4b-e are described. All compounds were characterized by IR, UV/Vis, MS, 1H, 13C and 19F NMR as well as elemental analyses. Phenyl(phthalocyaninato)indium(III) (4f) was prepared by the reaction of (n-C5H11)8PcInCl (4a) with PhLi. The high solubility of the complexes 3a-e and 4a-f is, aside from the influence of the peripheral substituents, considered to be derived from the large dipole moments present which are due to the strongly electron withdrawing axial ligands, and from the lower tendency of axially substituted phthalocyaninato metal complexes to form aggregates.
    Type of Medium: Electronic Resource
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