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  • 1
    Electronic Resource
    Electronic Resource
    New Synthesis of trans-Disubstituted Cyclam Macrocycles - Elucidation of the Disubstitution Mechanism on the Basis of X-ray Data and Molecular Modeling (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1971-1975 
    Details
    ISSN: 1434-193X
    Keywords: Cyclam ; Substitution ; Reaction ; Molecular modeling ; Electrostatic potential ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new way to synthesize trans-disubstituted cyclam tetraazamacrocycles 1 is reported. The synthesis proceeds in three steps via the tricyclic 1,4,8,11-tetraazatricyclo[9.3.1.14,8]hexadecane system 2, which can be selectively dialkylated and hydrolyzed under basic conditions to give the final product 1. An understanding of the reactivity, based on the X-ray experimental electrostatic potential and molecular modeling of the 1,4,8,11-tetraazatricyclo[9.3.1.14,8]hexadecane macrotricycle, has permitted the elucidation of a new reaction pathway leading to the trans-disubstituted cyclam.Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2046/1998/97294_s.pdf or from the author.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Syntheses, Structures, and Reactivity of 2,5-Diboryl-1-alkylpyrroles and Di(1-alkyl-2-pyrrolyl)boranes (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 399-404 
    Details
    ISSN: 1434-1948
    Keywords: Boranes ; 1-Alkylpyrroles ; Porphyrinogenes ; Lithiation ; Tin-boron exchange ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of 2,5-dilithiated 1-methylpyrrole (1a) with ClB(NR2)2 lead to the novel 2,5-diboryl-1-methylpyrroles 2a and 2b. Accordingly, 2,5-diboryl-1-benzylpyrrole 2d is obtained. 1a and Cl2BNiPr2 form the aminochloroboryl-substituted derivative 2c and the di(5-boryl-2-pyrrolyl)borane 4 in 29% and 15% yield, respectively. The 2,5-distannyl-1-methylpyrrole 1c is used for the synthesis of the aryloxy-boryl derivative 2e. Reacting monolithiated 1-methyl- and 1-benzylpyrroles with Cl2BNiPr2 yields the di(2-pyrrolyl)boranes 3e and 3f, respectively. NMR and MS data are in agreement with the compositions of the compounds, which are confirmed by X-ray structure analyses for 2a, 2b, 2d, und 3e.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
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