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  • Thermal reaction of [3,4]-benzo-8-substituted-3Z,5Z,7E-octatetraenes and quantum-chemical study of the (8π,6π)-electrocyclisation
    Škorić, Irena; Pavošević, Fabijan; Vazdar, Mario; Marinić, Željko; Šindler-Kulyk, Marija; Eckert-Maksić, Mirjana; Margetić, Davor

    Organic & biomolecular chemistry, 10/2011, Letnik: 9, Številka: 19
    Journal Article

    The first example of thermal (8π,6π)-electrocyclisation of 1,3,5,7-octatetraene with one double bond embedded in an aromatic moiety is described. By this process, 3,4-benzo-8-substituted octatetraene derivatives, the cis,trans-1-(o-vinylphenyl)-4-(R = Me, Ph, 2-furyl)buta-1,3-dienes were transformed to a new endo-7-(R = Me, Ph, 2-furyl) and exo-7-(R = Me)-2,3-benzobicyclo4.2.0octa-2,4-dienes. Mechanism of reaction was also studied by DFT quantum-chemical calculations. The M06/6-311+G(d,p)//M06/6-31+G(d,p) calculations indicate that formation of the single endo-isomer in the case of phenyl and 2-furyl substituents is determined by higher activation barriers for exo-6π-electrocyclisation than for 8π-cycloreversion.

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