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  • 1
    Electronic Resource
    Electronic Resource
    Crystallization of Large Planar Polycyclic Aromatic Hydrocarbons: The Molecular and Crystal Structures of Hexabenzo[bc,ef,hi,kl,no,qr]coronene and Benzo[1,2,3-bc:4,5,6-b'c']dicoronene (1995)
    s.l. : American Chemical Society
    Journal of the American Chemical Society 117 (1995), S. 30-41 
    Details
    ISSN: 1520-5126
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/ja00106a004
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  • 2
    Electronic Resource
    Electronic Resource
    Transanulare Wechselwirkungen bei [3.3]Phanen, III. [3.3]Paracyclophan, neue Synthesen, Sessel- und Wannen-Konformation (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 249-259 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Transanular Interactions in [3.3]Phanes, III. [3.3]Paracyclophane, New Syntheses, Chair and Boat Conformation[3.3]Paracyclophane (1) was synthesized via the 2,13-dithia[4.4]paracyclophane (2) by vapor phase pyrolysis of the disulfone 3 obtained from 2. Reaction of 2 with benzyne gave trans- and cis-2,1 l-bis(phenylthio)[3.3]paracyclophane (4 and 5) by Stevens rearrangement. Oxidation to the sulfoxides 6 and 7 and pyrolysis yielded the [3.3]paracyclophanedienes (12/13) giving 1 on catalytic hydrogenation. Large substituents in the 2,11-positions of the bridges stabilize the two conformers of 1, based on 1H-NMR spectra the trans-isomer 4 has the chair, the cis-isomer 5 the boat conformation.
    Notes: [3.3]Paracyclophan (1) wurde über 2,13-Dithia[4.4]paracyclophan (2) durch Gasphasen-Pyrolyse des aus 2 erhaltenen Disulfons 3 synthetisiert. Reaktion von Dehydrobenzol mit 2 ergab durch Stevens-Umlagerung trans- und cis-2,11-Bis(phenylthio)[3.3]paracyclophan (4 und 5); durch Oxidation zu den Sulfoxiden 6 und 7 und Pyrolyse wurden die [3.3]Paracyclophandiene (12/13) erhalten, die bei katalytischer Hydrierung 1 ergaben. Große Substituenten in den 2,11-Positionen der Brücken stabilisieren die beiden Konformere von 1, laut 1H-NMR-Spektren liegt das trans-Isomere 4 in der Sessel-, das cis-Isomere 5 in der Wannen-Konformation vor.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791120122
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  • 3
    Electronic Resource
    Electronic Resource
    Transanulare Wechselwirkung bei [m. n]Phanen, 27. Modelle für Excimere und Exciplexe: [2.2]Phane des Fluorens, 9-Fluorenons und 9-Fluorenyl-Anions (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 144-162 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Transanular Interaction in [m. n]Phanes, 27. Models for Excimers and Exciplexes: [2.2]Phanes of Fluorene, 9-Fluorenone, and 9-Fluorenyl Anionanti- and syn-[2.2](2,7)-fluorenophane (1, 2) as well as their 5,16-dioxo and 5-oxo derivatives 3, 5, and 6 containing two or one 9-fluorenone units were synthesized: Cyclisation of the bis(bromomethyl) compounds 7 and 10 with the bis(mercaptomethyl) compounds 9 and 12 gave the dithia[3.3]phanes 14, 16, and 18 containing fluorene and 9-fluorenone units bridged at the 2,7-positions. Oxidation to the disulfones 15, 17, and 18 and vapour phase pyrolysis (500°C, 0.1 Torr) led to 1/2, 3, and 5/6, respectively. The molecular geometry of 1 was determined by X-ray structure analysis. On treatment of suspensions of 1 and 2 in hexamethylphosphoric triamide with n-butyllithium in n-hexane red solutions of the dianions 21 and 22 were generated, which were characterized by 1H NMR spectroscopy. With deuterium oxide the dianion 22 yielded [exo-5, exo-16-D2]-anti-[2.2](2,7)fluorenophane (24), with methyl iodide exo-5, exo-16-dimethyl-anti-[2.2](2,7)fluorenophane (26). Multiple metalation with n-butyllithium and reaction with methyl iodide led to 5,5,16,16-tetramethyl-anti-[2.2](2,7)fluorenophane (27).
    Notes: anti- und syn-[2,2](2,7)Fluorenophan (1, 2) sowie ihre 5,16-Dioxo- und 5-Oxoverbindungen 3, 5 und 6 mit zwei bzw. einer 9-Fluorenon-Einheit wurden synthetisiert: Cyclisierung der Bis(brommethyl)-Verbindungen 7 und 10 mit den Bis(mercaptomethyl)-Verbindungen 9 und 12 ergab die Dithia[3.3]phane 14, 16 und 18 mit in 2,7-Position verbrückten Fluoren- und 9-Fluorenon-Einheiten. Oxidation zu den Disulfonen 15, 17 und 18 und Gasphasen-Pyrolyse (500°C, 0.1 Torr) führte zu 1/2, 3 bzw. 5/6. Die Molekülgeometrie von 1 wurde durch Röntgenstrukturanalyse bestimmt. Suspensonen von 1 und 2 in Hexamethylphosphorsäuretriamid ergaben mit n-Butyllithium in n-Hexan rote Lösungen der Dianionen 21 und 22, die durch 1H-NMR-Spektroskopie charakterisiert wurden. Aus dem Dianion 22 erhielt man mit Deuteriumoxid [exo-5, exo-16-D2]-anti-[2.2](2,7)Fluorenophan (24), mit Methyliodid exo-5, exo-16-Dimethyl-anti-[2.2](2,7)fluorenophan (26). Mehrfache Metallierung mit n-Butyllithium und Reaktion mit Methyliodid führte zu 5,5,16,16-Tetramethyl-anti-[2.2](2,7)fluorenophan (27).
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180115
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  • 4
    Electronic Resource
    Electronic Resource
    Transanulare Wechselwirkung bei [m. n]Phanen, 28. Modelle für Excimere und Exciplexe: Absorptions- und Emissionsspektren von [2.2]Phanen des Fluorens und 9-Fluorenons (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 163-175 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Transanular Interaction in [m. n]Phanes, 28 Models for Excimers and Exciplexes: Absorption and Emission Spectra of [2.2]Phanes of Fluorene and 9-FluorenoneThe absorption, fluorescene, and phosphorescence spectra of anti- and syn-[2.2](2,7)fluorenophane (1 and 2) as well as their zero field splitting parameters | D | of the excited triplet state determined by ODMR measurements are discussed with regard to the electronic interactions in dependence of the mutual orientation of the fluorene units. As 9-fluorenone, the corresponding [2.2]phanes 3, 5, and 6 which contain 9-fluorenone units do not show emission from the excited triplet state. From the two pairs of syn-anti-isomers 2/1 and 6/5 the syn-isomers 2 and 6 having “eclipsed” fluorene carbon atoms show the stronger electronic interactions.
    Notes: Die Absorptions-, Fluoreszenz- und Phosphoreszenzspektren von anti- und syn-[2.2](2,7)Fluorenophan (1 und 2) sowie ihre durch ODMR-Messungen bestimmten Nullfeldaufspaltungsparameter | D | des angeregten Triplettzustandes werden im Hinblick auf die Elektronenwechselwirkung und deren Orientierungsabhängigkeit diskutiert. Die entsprechenden [2.2]Phane 3, 5 und 6, die 9-Fluorenon-Einheiten enthalten, zeigen wie 9-Fluorenon keine Emission aus dem angeregten Triplettzustand. Von beiden syn-anti-Isomerenpaaren 2/1 und 6/5 zeigen jeweils die syn-Isomeren 2 und 6 mit „ekliptischer“ Anordnung der Fluoren-Kohlenstoffatome die stärkere Elektronenwechselwirkung.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180116
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  • 5
    Electronic Resource
    Electronic Resource
    Transanulare Wechselwirkung bei [m.n]Phanen, 29. Modelle für Amin-Aromaten-Exciplexe: π-π- versus n-π-Wechselwirkung bei isomeren [2]Naphthalino[2](2,6)pyridinophanen und [2]Naphthalino[2](2,6)pyridinophan-1,11-dienen (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 4884-4906 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Transanular Interaction in [m.n]Phanes, 29. Models for Amine-Arene-Exciplexes: π-π versus n-π Interaction in Isomeric [2]Naphthalino[2](2,6)pyridinophanes and [2]Naphthalino[2](2,6)pyridinophane-1,11-dienesThe [2.2]naphthalinopyridinophanes 5, 6 and the corresponding dienes 3, 4 were synthesized as models for exciplexes. From the dithia[3.3]phanes 10 and 12, prepared by cyclisation of 7 with 9 and 8 with 9, the [2.2]phanes 5 and 6 were obtained by oxidation to the disulfones 11, 13 followed by vapour phase pyrolysis. Ring contraction of 10, 12 by S-analogous Wittig ether rearrangement led to 14/15 and 17/18, respectively. 14 and 17 were converted into the dienes 3 and 4 via oxidation to the sulfoxides 16, 19 and pyrolytic elimination of methanesulfenic acid. The 1H NMR data correspond to the perpendicular orientation of pyridine and naphthalene in 3, 4 and to more parallel arrangements of the aromatic units in 5, 6. For the conformational flipping of the pyridine ring in 5 an energy barrier of ΔH± = 11.84 ± 0.15 kcal/mol and ΔS± = -1.70 ± 0.58 cal K-1 mol-1 was obtained by temperature dependent 1H NMR and line shape analysis. The molecular structures of 3, 5, and 6 were determined by X-ray analysis. Absorption spectra and especially the red-shifted structureless fluorescence emissions typical for exciplexes show orientational dependencies and are discussed in terms of n-π interaction between pyridine nitrogen and naphthalene in 3, 4 and π-π interaction between the aromatic units in 5, 6.
    Notes: Als Exciplex-Modelle wurden die [2.2]Naphthalinopyridinophane 5, 6 und die entsprechenden Diene 3, 4 synthetisiert: Aus den Dithia[3.3]phanen 10 und 12, dargestellt durch Cyclisierung von 7 mit 9 und 8 mit 9, wurden die [2.2]Phane 5 und 6 durch Oxidation zu den Disulfonen 11, 13 und deren Pyrolyse in der Gasphase erhalten. Ringverengung von 10, 12 durch S-analoge Wittig-Etherumlagerung ergab 14/15 bzw. 17/18. 14 und 17 wurden durch Oxidation zu den Sulfoxiden 16, 19 und pyrolytische Eliminierung von Methansulfensäure in die Diene 3 und 4 übergeführt. Die 1H-NMR-Daten entsprechen der senkrechten Anordnung von Pyridin und Naphthalin in 3, 4 und mehr parallelen Orientierungen der Aromaten-Einheiten in 5, 6. Temperaturabhängige 1H-NMR und Linienformanalyse ergaben für das Umklappen des Pyridin-Ringes in 5 eine Energiebarriere von ΔH± = 11.84 ± 0.15 kcal/mol und ΔS± = -1.70 ± 0.58 cal K-1 mol-1. Die Molekülstrukturen von 3, 5 und 6 wurden durch Röntgenstrukturanalyse bestimmt. Absorptionsspektren und vor allem die für Exciplexe typisch rotverschobenen und strukturlosen Fluoreszenz-Emissionen von 3-6 zeigen Orientierungsabhängigkeiten und werden mit n-π-Wechselwirkung zwischen dem Pyridin-Stickstoff und Naphthalin in 3, 4 und π-π-Wechselwirkung zwischen den Aromaten-Einheiten in 5, 6 interpretiert.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181223
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  • 6
    Electronic Resource
    Electronic Resource
    Bidentate Phosphines of Heteroarenes: 4,6-Bis(diphenylphosphino)dibenzofuran and 4,6-Bis(diphenylphosphino)dibenzothiophene (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1705-1710 
    Details
    ISSN: 0009-2940
    Keywords: Phosphine ligands ; Dibenzofuran ; Dibenzothiophene ; Lithium compounds ; Multiple lithiation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Twofold lithiation of dibenzofuran (6) and dibenzothiophene (12) with n-butyllithium/N,N,N′,N′-tetramethylethylenediamine (TMEDA) in n-hexane or n-pentane followed by the reaction with chlorodiphenylphosphine yielded the title compounds 4 and 5, respectively, The monophosphines 4-(diphenylphosphino)dibenzofuran (11) and 4-(diphenylphosphino)dibenzothiophene (15) were obtained analogously via the monolithium compounds 9 and 14 of the heteroarenes. In the case of dibenzofuran (6), it was shown that mono- and dilithiation is controlled by temperature.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240806
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  • 7
    Electronic Resource
    Electronic Resource
    Transanulare Wechselwirkung bei [m. n]Phanen, 26. Modelle für Excimere: Achirales und chirales [2.2](2,6)Naphthalinophan (1983)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 116 (1983), S. 827-832 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Transanular Interactions in [m. n]Phanes, 26. Models for Excimers: Achiral and Chiral [2.2](2,6)NaphthalinophaneThe achiral [2.2](2,6)naphthalenophane diastereomer 1 which was not obtained previously, was synthesized by using dibromo-substitution to force the formation of 3 besides 4 in the vacuum pyrolysis of the disulfone 12. Debromination of 3/4 via halogen-metal-exchange followed by hydrolysis gave a mixture of 1/2 from which 1 could be isolated and characterized.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19831160240
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  • 8
    Electronic Resource
    Electronic Resource
    Transanulare Wechselwirkung bei [m.n.]Phanen, 31. S-Analoge Wittig-Etherumlagerung von Thioethern in Dithia[3.3]phanen mit Alkalimetall-bis(trimethylsilyl)amiden (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 4922-4933 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Transanular Interaction in [m.n]Phanes, 31. S-Analogous Wittig-Ether Rearrangement of Thioethers in Dithia[3.3]phanes by means of Alkali Metal Bis(trimethylsilyl)amidesThe dithia[3.3]phanes 5-8 containing naphthalene and pyridine or pyrazine units were ring-contracted by reaction with alkali metal bis(trimethylsilyl)amides and subsequent methylation of the thiolate anions giving the bis(methylthio) substituted [2.2]phanes 9-12 in high yields. With lithium bis(trimethylsilyl)amide in tetrahydrofuran the stereoisomers 9a-12a were obtained as the main products whereas the sodium base in toluene yielded mainly 9b-11b and 12b/c.
    Notes: Die Dithia[3.3]phane 5-8 mit Naphthalin und Pyridin- bzw. Pyrazin-Einheiten ließen sich durch Reaktion mit Alkalimetall-bis(trimethylsilyl)amiden und Methylierung der Thiolat-Anionen in guten Ausbeuten zu den bis(methylthio)substituierten [2.2]Phanen 9-12 ringverengen. Mit Lithium-bis(trimethylsilyl)amid in Tetrahydrofuran wurden als Hauptprodukte die Stereoisomeren 9a-12a erhalten, während die Natrium-Base in Toluol überwiegend zu 9b-11b und 12b/c führte.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181225
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  • 9
    Electronic Resource
    Electronic Resource
    Transanulare Wechselwirkung bei [m.n]Phanen, 30. Modelle für Amin-Aromaten-Exciplexe: Isomere [2]Naphthalino[2](2,6)pyrazinophane und [2]Naphthalino[2](2,6)pyrazinophan-1,11-diene (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 4907-4921 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Transanular Interaction in [m.n]Phanes, 30. Models for Amine-Arene-Exciplexes: Isomeric [2]Naphthalino[2](2,6)pyrazinophanes and [2]Naphthalino[2](2,6)pyrazinophane-1,11-dienesThe [2.2]naphthalinopyrazinophanes 7, 8 and the corresponding dienes 3, 4 were synthesized as models for exciplexes. The dithia[3.3]phanes 20 and 22, prepared by cyclisation of 11 with 12 and 11 with 16, were oxidized to the disulfones 21, 23 which on vapour phase pyrolysis gave 7, 8. Ring contraction of 20, 22 by S-analogous Wittig ether rearrangement led to 24 and 26 which were converted to the dienes 3 and 4 via oxidation to the sulfoxides 25, 27 and pyrolytic elimination of methane sulfenic acid. Absorption and fluorescence spectra of 3, 4, 7, 8 as well as phosphorescence emission, observed for 7 and 8, are discussed in terms of n-π interaction between one pyrazine nitrogen and naphthalene in 3, 4 and π-π interaction between the aromatic units in 7, 8. For 7 and 8 the zero field splitting parameters |D| and |E| of the excited triplet state are determined by ODMR measurements.
    Notes: Als Exciplex-Modelle wurden die [2.2]Naphthalinopyrazinophane 7, 8 und die entsprechenden Diene 3, 4 synthetisiert: Die Dithia[3.3]phane 20 und 22, dargestellt durch Cyclisierung von 11 mit 12 und 11 mit 16, wurden zu den Disulfonen 21, 23 oxidiert, deren Pyrolyse in der Gasphase 7, 8 ergab. Ringverengung von 20, 22 durch S-analoge Wittig-Etherumlagerung ergab 24 bzw. 26, deren Oxidation zu den Sulfoxiden 25, 27 und pyrolytische Eliminierung von Methansulfensäure zu den Dienen 3 und 4 führte. Absorptions- und Fluoreszenzspektren von 3, 4, 7, 8 sowie die für 7 und 8 beobachtete Phosphoreszenz-Emission werden im Hinblick auf n-π-Wechselwirkung zwischen einem Pyrazin-Stickstoff und Naphthalin in 3, 4 und π-π-Wechselwirkung zwischen den Aromaten-Einheiten in 7, 8 diskutiert. Von 7 und 8 wurden die Nullfeld-Aufspaltungsparameter |D| und |E| des angeregten Triplettzustandes über ODMR-Messungen bestimmt.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181224
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  • 10
    Electronic Resource
    Electronic Resource
    1,8-Bis(diphenylphosphino)anthracene and Metal Complexes1) (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 333-336 
    Details
    ISSN: 0009-2940
    Keywords: Phosphine ligand ; Anthracene ; Nickel(II) complexes ; Palladium(II) complexes ; Cyclometallated chelate complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The title compound 4 was synthesized from dipotassium 1,8-anthracenedisulfonate (9) and potassium diphenylphosphide (Ph2PK). On reaction of 4 with nickel(II) chloride and bis-(benzonitrile)palladium(II) chloride, cyclometallation of the C - H bond in anthracene 9-position led to the square-planar chelate complexes 11 and 13, respectively. In the case of the palladium complex 13, the cyclometallated structure was proved by X-ray structure analysis. Treatment with aqueous potassium cyanide did not remove nickel from 11, but converted 11 into 12 by substitution of chloride with cyanide, demonstrating the high stability of these cyclometallated chelate complexes.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240214
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