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  • Cyclophanes  (21)
  • Template synthesis  (5)
  • Helical molecules  (4)
  • 1
    Electronic Resource
    Electronic Resource
    Intra- und extraannular funktionalisierte [2.2.2]Phane mit Dreifachbindung: Synthese und Eigenschaften (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1223-1227 
    Details
    ISSN: 0009-2940
    Keywords: Cesium effect ; Clathrate ; Cyclophanes ; Acetylene, diphenyl ; Rigid-group principle ; Tolane ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Intra- and Extraannularly Functionalized [2.2.2]Phanes: Syntheses and PropertiesThe severely strained new cyclophanes 7b-f, consisting of bridged tolane subunits and bearing intraannular substituents R, were prepared mainly to study steric interactions of R with the “π cloud” of the triple bond. These compounds exist in a rigid twisted conformation, whereas the unsubstituted reference compound 7a and the extraannularly functionalized azo compound 9 show C2 symmetry. 9 forms a 1 : 1 clathrate with toluene.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240540
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  • 2
    Electronic Resource
    Electronic Resource
    Konkave Makroheterocyclen (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 1713-1721 
    Details
    ISSN: 0009-2940
    Keywords: Concave molecules ; Cyclophanes ; High-dilution principle ; Macrocycles ; Spheriphanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Concave MacroheterocyclesMacrocyclic compounds of the general type 2 having a spherical shape and a molecular cavity have been synthesized. A „fold and paste“-type cyclization step generates the macroheterocycles 4, 10, 11, 14, and 21. Since this approach is difficult to apply for O-substituted derivatives, the „spheriphane“ 24 was synthesized by intermolecular cyclizaiton. The X-ray structure analysis of 11 shows intermolecular interactions („dimer formation“) in the crystal.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260731
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  • 3
    Electronic Resource
    Electronic Resource
    Auf dem Weg zu makrocyclischen para-Phenylenen (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 1723-1732 
    Details
    ISSN: 0009-2940
    Keywords: Cyclohexanes ; Cyclohexanones ; Cyclophanes ; Macrocycles ; Paracyclophanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On the Way to Macrocyclic para-PhenylenesStrategies are presented to synthesize the hitherto unknown [On]Paracyclophanes 1. Open chain belt-type molecules based on 1,4-connected carbocyclic six-membered rings were prepared. Functionalization of the outer rings in 4-position is the prerequisite for cyclization or lengthening of the molecular belts. In order to obtain the macrocyclic target molecules 1, well preorganized cis-isomers of 1,4-disubstituted cyclohexanes were prepared. X-ray structural analyses reveal the static stereochemistry of the intermediates 8, 9, 17, 18, and 24. The macrocyclic hydrocarbon 29 containing five cyclohexylidene units was detected.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260732
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  • 4
    Electronic Resource
    Electronic Resource
    A Chiral Adamantanophane: Preparation, Enantiomer Separation, Theoretical and Experimental Circular Dichroism and Absolute Configuration (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 2081-2088 
    Details
    ISSN: 0009-2940
    Keywords: Adamantanophanes ; Calculations, CI ; Circular dichroism ; Cyclophanes ; Strain energy ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Exchange of aromatic units (e.g. benzene) for aliphatic/ali-cyclic building blocks (e.g. adamantane) in cyclophanes leads to molecules of the “araliphane” type. The synthesis of the highly strained [2.2](1,3)adamantanometacyclophanes 5a-c is described. The cyclophane skeletons of these molecules are conformationally rigid and therefore 5a-c are planar-chiral. The circular dichroism of 5c has been calculated theoretically with NDDO/MRD-CI methods and was measured. Agreement of theory and experiment is good, a comparison of both allows the assignment of the absolute configuration of the two enantiomers of 5c with high probability. Furthermore, analysis of the nπ* band in the CD spectrum yields a, simple general rule to determine the conformation of the carboxyl group in phenyl ester substructures. Theoretical calculations of the strain energy (Es) of 5c reveal the distribution of strain within the molecule.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941271034
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  • 5
    Electronic Resource
    Electronic Resource
    Ein neues, Deltaphan und bandförmige Cyclophane (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 2089-2096 
    Details
    ISSN: 0009-2940
    Keywords: Aza-phanes ; Cyclophanes ; Molecular belts ; Macrocycles ; CH-π interaction ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A New Deltaphane and Ribbon-Shaped CyclophanesThe reaction of the fourfold functionalized [3.3][3.3]metacyclophane 8 with tosylamide monosodium salt leads to a new deltaphane in quantitative yield. An X-ray analysis confirms the belt-shaped structure of 3. Moreover, a series 10-15 of well-soluble belt-shaped macrocycles with up to 21 interconnected benzene rings were detected. The intermediate [3.3][3.3]metacyclophane 4 shows remarkably short distances to enclosed toluene, one toluene molecule acting twice as a π acceptor and once as a π donor. Competition experiments with benzene demonstrate the dependence of conformational behaviour on the solvent.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941271035
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  • 6
    Electronic Resource
    Electronic Resource
    Templat-Synthese makrobicyclischer Großhohlräume vom Tris(bipyridin)-Typ (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 1725-1727 
    Details
    ISSN: 0009-2940
    Keywords: Cryptands ; Macrobicyclic ligands ; Template synthesis ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Template Synthesis of Macrobicyclic Large Cavities of the Tris-(bipyridine)-TypeThe synthesis of the ligands 2 and 3 has been performed in a one-step procedure starting with the triamines 11 and 12 and 5,5′-bis(bromomethyl)-2,2′-bipyridine (6). The new macrobicyclic compounds were isolated and characterized as their sodium complexes. Dynamic 1H-NMR investigations reveal the conformational flexibility of the complex 2 · Na⊕.
    Notes: Die Liganden 2 und 3 wurden in einer Eintopf-Synthese ausgehend von den Triaminen 11 und 12 sowie 5,5′-Bis(brommethyl-2,2′-bipyridin (6) erhalten und als Natrium-Komplexe isoliert und charakterisiert. Die dynamische 1H-NMR-Spektroskopie des Komplexes 2 · Na⊕ belegt seine konformative Beweglichkeit.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891220920
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  • 7
    Electronic Resource
    Electronic Resource
    Ketonpyrolyse: Darstellung und Röntgen-Kristallstruktur eines Oxa[3.2.1]cyclophans (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1283-1285 
    Details
    ISSN: 0009-2940
    Keywords: Cyclophanes ; Flash pyrolysis ; Ketone pyrolysis ; [3.3]Metacyclophanes ; Oxacyclophanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ketone Pyrolysis: Preparation and X-ray Structure Analysis of an Oxa[3.2.1]cyclophaneThe oxa[3.2.1]cyclophane 2 was obtained for the first time in the course of the thermal extrusion of carbon monoxide from the dimethoxy[3.3]metacyclophanedione 1. The X-ray structure analyses of 1 and 2 are reported. 1 shows a syn-type conformation.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250539
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  • 8
    Electronic Resource
    Electronic Resource
    Von vierfach funktionalisierten Cyclophanen zu rohrförmigen Molekülen (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1881-1887 
    Details
    ISSN: 0009-2940
    Keywords: Heteraphanes ; Cyclophanes ; Macrocycles ; Tube-shaped molecules ; Phanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From Fourfold Functionalized Cyclophanes to Tube-Shaped MoleculesA series of fourfold functionalized 2,11-dithia- and 2,11-diaza[3.3]cyclophanes 15-17 and 18-22, resp., is prepared by using a new multistep-strategy starting from 7 or m-xylene, respectively. The cyclophanes are used to construct tube-shaped molecules of type 24 by macrocyclization reactions of e. g. 21 and 22. Macrocycle 24 turns out to be conformationally flexible.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250815
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  • 9
    Electronic Resource
    Electronic Resource
    Gürtelförmige Moleküle mittels repetitiver Synthesestrategie (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 767-777 
    Details
    ISSN: 0009-2940
    Keywords: Azaphanes ; Cyclophanes ; Macrocycles ; Molecular belts ; Multistep strategy ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Belt-Shaped Molecules by a Repetitive Synthetic StrategyBelt-shaped molecules of the general type 2 containing up to five benzene ring units (cf. 37) have been synthesized by macrocyclisation reactions of ribbon-shaped precursors. An intermolecular cyclization step generates the macroheterocycles 38 and 40. The fourfold-bridged cyclophane 36 are prepared by intra-and intermolecular cyclization reactions. The X-ray structure analyses of 14, 16, 22, 23, 28, and 36 show S-shaped conformations of the molecules.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270428
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  • 10
    Electronic Resource
    Electronic Resource
    Chiral Metal Carbene Modified [2.2]Metacyclophanes: Synthesis, Structure, and Chiroptic Properties (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 1105-1111 
    Details
    ISSN: 0009-2940
    Keywords: Carbene complexes ; Chromium ; Cyclophanes ; Chirality ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pentacarbonyl(4-[2.2]metacyclophanyl(methoxy)carbene)-chromium(0) (6) was prepared according to the Fischer route from 4-bromo[2.2]metacyclophane. Aminolysis with non-chiral and chiral amines affords aminocarbene complexes 7-12. X-Ray structure analyses for 6 and its aminocarbene analogs 7 and 8 indicate that the incorporation of the chromium-carbene fragment has no significant influence on the deformation of the [2.2]metacyclophane skeleton.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971300812
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