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  • 1
    Electronic Resource
    Electronic Resource
    Zur Konjugation in makrocyclischen Bindungssystemen, XIX. Benzo[12]annulene: Darstellung, Stereochemie und transannulare Reaktionen von Tribenzol[a.e.i]cyclododecenen (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 1159-1169 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Conjugation in Macrocyclic Systems, XIX. Benzo[12]annulenes: Syntheses, Stereochemistry and Transannular Reactions of Tribenzo[a.e.i]cyclododecenesTribenzo[a.e.i]cyclododecene (tribenzo[12]annulene, 2) was prepared by a double Wittig reaction from phthalaldehyde and the diylide from 2.2′-bis(bromomethyl)-trans-stilbene and triphenylphosphine. The structure of 4, a side-product of this reaction, has been established. The formation of 4 by [2+2+2]-cycloaddition from 5 is discussed. Attempts to prepare 5 by partial hydrogenation of 6 and 1 resulted also in the formation of 4 together with other hydrogenation products, the structures of which have been partly established. 1H n.m.r, i.r. and u.v. spectra of the compounds obtained are discussed with regard to structure and stereochemistry.
    Notes: Durch doppelte Wittig-Reaktion von Phthaldialdehyd mit dem aus 2.2′-Bis-brommethyl-trans-stilben und Triphenylphosphin erhaltenen Diylid wird Tribenzo[a.e.i]cyclododecen (Tribenzo[12]annulen, 2) dargestellt. Die Struktur der als Nebenprodukt bei der 2-Synthese erhaltenen Verbindung 4 wurde aufgeklärt. Die Bildung von 4 durch transannulare [2+2+2]-Cycloaddition aus 5 wird diskutiert. Versuche zur Darstellung von 5, durch partielle Hydrierung von 6 und 1 ergaben ebenfalls 4 neben anderen Hydrierungsprodukten, deren Struktur teilweise aufgeklärt wurde. 1H-NMR-, IR- und UV-Spektren der erhaltenen Verbindungen werden im Hinblick auf Struktur und Stereochemie diskutiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040420
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  • 2
    Electronic Resource
    Electronic Resource
    Intramolekulare Wechselwirkungen zwischen Dreifachbindungen, VI Parallele Dreifachbindungen: Versuche zur Synthese des 7.8.15.16-Tetradehydro-cyclodeca[1.2.3-de: 6.7.8-d′ e′]-dinaphthalins (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 1182-1190 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Interactions of Triple Bonds, VI. Parallel Triple Bonds: Attempted Synthesis of 7.8.15.16-Tetradehydrocyclodecal[1.2.3-de:6.7.8-d′ e′] dinaphthalene1-Ethynyl-8-iodonaphthalene (4) and 1.8-diethynylnaphthalene (5) were prepared. Coupling of 4 in pyridine as the copper acetylide did not yield 2 but dibenzo [de, mn]naphthacene (13) and the diacenaphtho-fluoranthene 14, the formation of which is discussed. 13 was also formed in the reaction of 5 with 1.8-diiodonaphthalene. - Spectra and reactivity of 5 were investigated with regard to triple bond interactions. Lindlar hydrogenation of 5 yielded the abnormal hydrogenation product 10 via 11, which could be trapped in the presence of maleic anhydride.
    Notes: 8-Jod-l-äthinyl-naphthalin (4) und 1.8-Diäthinyl-naphthalin (5) wurden dargestellt. Kupplung von 4 als Kupferacetylid in Pyridin ergab nicht das erwartete 2, sondern Dibenzo[de, mn] - naphthacen (13) und das Diacenaphtho-fluoranthen 14, deren Bildungsweise diskutiert wird. 13 wurde auch bei der entsprechend durchgeführten Reaktion von 5 mit 1.8-Dijod-naphthalin nachgewiesen. - Die Wechselwirkung zwischen den Dreifachbindungen in 5 wurde an Hand der Spektren und der Reaktivität untersucht. Bei der Lindlar-Hydrierung von 5 entstand das anormale Hydrierungsprodukt 10 über 11, das mit Maleinsäureanhydrid als 12 abgefangen werden konnte.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040422
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  • 3
    Electronic Resource
    Electronic Resource
    Intramolekulare Wechselwirkungen zwischen Dreifachbindungen, VII. Parallele Dreifachbindungen: 1.8-Bis-[alkin-(1)-yl]-naphthaline (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 1191-1198 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Interactions of Triple Bonds, VII. Parallel Triple Bonds: 1.8-Bis(1-alkynyl)naphthalenesThe dilithium acetylide 2 of 1.8-diethynylnaphthalene reacted with methyl iodide to yield 3 (R = CH3) and with 1.3-diiodopropane and 1.4-diiodobutane to afford the cyclic diacetylenes 4 (n = 1 and 2, resp.). Oxygen and nitrogen analogues to 4 (n = 1) were also prepared starting from 2 (5, 8). Transannular triple bond interactions in these compounds are discussed based on i.r., u. v., and 1H n.m.r. spectra. Unsuccessful attempts to prepare 9 are reported.
    Notes: Das Dilithiumacetylid 2 des 1.8-Diäthinyl-naphthalins wurde mit Methyljodid zu 3 (R = CH3) und mit 1.3-Dijod-propan bzw. 1.4-Dijod-butan zu den cyclischen Diacetylenen 4 (n = 1 bzw. 2) umgesetzt. Sauerstoff- und Stickstoff-Analoga zu 4 (n = 1) wurden ebenfalls ausgehend von 2 synthetisiert (5, 8). Die transannulare Wechselwirkung zwischen den Dreifach bindungen in den erhaltenen Verbindungen wird an Hand von IR-, UV- und 1H-NMR-Spektren diskutiert. Über negative Versuche zur Darstellung von 9 wird berichtet.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040423
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  • 4
    Electronic Resource
    Electronic Resource
    Intramolekulare Wechselwirkungen zwischen Dreifachbindungen, XII. 2.2′-Bis-[alkin-(1)-yl]-biphenyle (1972)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 105 (1972), S. 2310-2319 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Interactions of Triple Bonds, XII. 2.2′-Bis(1-alkynyl)biphenylsThe preparation of 2.2′-diethynylbiphenyl (2, R = H) was achieved by double Wittig reaction from 2.2′-bis(bromomethyl)biphenyl via 2.2′-divinylbiphenyl which by bromine addition and elimination of hydrogen bromide yielded 2 (R = H). Two other syntheses of 2 (R = H) are reported. 2 (R = H) reacted with hydrogen bromide under cross-linkage of the triple bonds to 9.10-bis(bromomethyl)phenanthrene (6). By catalytic hydrogenation 9.10-dimethylphenanthrene (5) was obtained in small yields in addition to the normal hydrogenation product 4.2.2′-Bis(1-propynyl)biphenyl (2, R = CH3) and the cyclic diacetylenes 3 (n = 2, 3 and 4) were obtained from 2 (R = H) via the dilithium acetylide by alkylation with the corresponding alkyl iodides.For 3 (n = 2) the potential barrier for the ring inversion was determined from temperature dependent 1H n.m.r. to be 17.9 ± 0.2 kcal/mole at TC = 87° (in 1-chloronaphthalene). The conformational stability of 3 (n = 2) is discussed in comparison to 1.
    Notes: Zur Darstellung von 2.2′-Diäthinyl-biphenyl (2, R = H) wurde durch doppelte Wittig-Reaktion aus 2.2′-Bis-brommethyl-biphenyl und Formaldehyd 2.2′-Divinyl-biphenyl dargestellt, das durch Brom-Addition und Bromwasserstoff-Eliminierung 2 (R = H) ergab. Zwei weitere Synthesen von 2 (R = H) werden angegeben. 2 (R = H) reagierte bei der Bromwasserstoff-Addition unter Wechselwirkung der Dreifachbindungen zu 9.10-Bis-brommethyl-phenanthren (6). Ebenso entstand bei der katalytischen Hydrierung neben dem normalen Hydrierungsprodukt 4 in geringer Ausbeute 9.10-Dimethyl-phenanthren (5).Aus 2 (R = H) wurden über das Dilithiumacetylid durch Alkylierung mit den betreffenden Alkyljodiden 2.2′-Bis-[propin-(1)-yl]-biphenyl (2, R = CH3) und die cyclischen Diacetylene 3 (n = 2, 3 und 4) erhalten.Aus der Temperaturabhängigkeit des 1H-NMR-Spektrums wurde für 3 (n = 2) die Potentialbarriere für die Ringinversion zu 17.9 ± 0.2 kcal/Mol bei TC = 87° (in 1-Chlor-naphthalin) bestimmt. Die konformative Stabilität von 3 (n = 2) im Vergleich zu 1 wird diskutiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19721050724
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  • 5
    Electronic Resource
    Electronic Resource
    Aromatic Radical Anions with Parallel or Crossed Triple Bonds (1977)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 60 (1977), S. 2530-2538 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Proton hyperfine data are reported for the radical anions of 1,8-di (propyn-1-yl)-naphthalene (I), 7,8,12,13-tetradehydro-10,11-dihydro-9H-cyclodeca[d,e]naphthalene (II) and 2,2′-di(propyn-1-yl)-biphenyl (III), as well as of 5,6,11,12-tetradehydro-7,8,9,10-tetrahydro-dibenzo[a,c]cyclodecene (IV) and its 8,8,9,9-tetradeuterio-derivative (IV-d4). The triple bonds in I and II can be regarded as roughly parallel, while those in IV (and IV-d4) may be considered as crossed. The π-spin distributions in I⊖ to IV⊖ are discussed in terms of simple MO models which suggest a weekly bonding interaction between the acetylenic fragments in IV⊖, in contrast to III⊖ where such an effect appears to be negligible. The importance of an analogous interaction in I⊖ and II⊖ is difficult to deduce, since its inclusion into a MO model does not substantially affect the π-spin distribution in these radical anions.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19770600806
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  • 6
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    Aromatic Radical Anions with Parallel or Crossed Triple Bonds (1977)
    Wiley
    Details
    Publication Date: 1977-12-14
    Print ISSN: 0018-019X
    Electronic ISSN: 1522-2675
    Topics: Chemistry and Pharmacology
    Published by Wiley
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