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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1759-1762 
    ISSN: 1434-193X
    Keywords: Alkenes ; Cycloadditions ; Cage compounds ; Ab initio calculations ; Double-bond pyramidalization ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The twofold bridged sesquinorbornenes 2 and 6 were prepared using sequential [4 + 2] cycloadditions of benzoquinone with 1,5-dihydropentalenes 1 and 5. These syntheses were improved using dilution conditions or a more reactive substituted benzoquinone. Results from semiempirical and ab initio DFT calculations indicated remarkably high pyramidalization angles (φ = 46-47°) for the central C-C double-bond atoms. The chemical reactivity with triplet and singlet oxygen, dimethyldioxirane and N-methyl-1,2,4-triazoline-3,5-dione supports these structural assignments.
    Type of Medium: Electronic Resource
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