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  • 1
    ISSN: 1434-193X
    Keywords: Cycloadditions ; Photochemistry ; Cage compounds ; Quinones ; Density functional calculations ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Thermal addition of o-benzoquinones to barrelenes (bicyclo[2.2.2]octatrienes) produces tetracyclic trienediones of type 1. These multichromophoric molecules offer a plethora of photochemical reactions of which the most interesting are (1) rearrangement and bisdecarbonylation of the enedione chromophore and (2) [2π + 2π] intramolecular cycloaddition of the face-to-face double bonds. Theoretical methods (semiempirical as well as density functional) were also used to investigate the spin multiplicity diversity of these reactions. The diketone 7 (bicyclo[2.2.2]octa-5,7-diene-2,3-dione) was investigated using He(I) photoelectron spectroscopy.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1471-1477 
    ISSN: 1434-193X
    Keywords: Cyclophanes ; Dilution principle ; Heterocycles ; Medium membered rings ; Ring strain ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The N-protected 1,10-diaza[2.2]metacyclo- and 1,10-diaza-[2]metacyclo[2](2,6)-pyridinophanes 4 and 5 have been synthesized for the first time using high dilution conditions. The free secondary diamine 7 was obtained from 4 by alkaline hydrolysis. - Quantum chemical calculations support the hypothesis that 7 is one of the most strained anti-hetera[2.2]metacyclophanes known. This is also evident from the 1H-NMR spectrum of 7, which shows one of the strongest high field shifts for the intraannular protons in comparison to other anti-[2.2]metacyclophanes.
    Type of Medium: Electronic Resource
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