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  • 1
    ISSN: 0009-2940
    Keywords: Oxanorbornadiene → oxepine isomerization, limitations ; [6 + 4] Tropone dimerization ; Diene enone [4 + 2] photocycloaddition, intramolecular ; Oxaquadricyclanes, X-ray structure, thermolysis ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Photochemical Transformations, 761). - Studies in the Area of the Oxanorbornadiene → Oxepine Isomerization. An Intramolecular Diene/Enone [4 + 2] PhotocycloadditionAt room temperature, the “tropone-annulated” oxanorborna diene 2b dimerizes regio- and stereospecifically to give a [6 + 4] adduct (5). Direct photoexcitation of this adduct induces intramolecular diene/enone [4 + 2] addition to 16 followed by a [2 + 2] cycloaddition to provide the dodecacycle 17. An X- ray crystal structure analysis of 17 documents the influence of the heteroatom and of the quasi-bisected ester functions on the length of the three types of oxaquadricyclane - three-membered ring bonds. Direct and sensitized excitation of 2b, c produces polymers; yet, after changing the troponoid chromophor (9, 10) oxaquadricyclane formation takes place (13, 14). In the thermolysis of the annulated oxaquadricyclanes (13, 14) the different cyclopropane C - C bonds are cleaved at a comparable rate.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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