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Issue 19, 2011
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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

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Abstract

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-benzobicyclo[4.2.0]octa-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.

Graphical abstract: Thermal reaction of [3,4]-benzo-8-substituted-3Z,5Z,7E-octatetraenes and quantum-chemical study of the (8π,6π)-electrocyclisation

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Article information


Submitted
23 May 2011
Accepted
30 Jun 2011
First published
01 Jul 2011

Org. Biomol. Chem., 2011,9, 6771-6778
Article type
Paper

Thermal reaction of [3,4]-benzo-8-substituted-3Z,5Z,7E-octatetraenes and quantum-chemical study of the (8π,6π)-electrocyclisation

I. Škorić, F. Pavošević, M. Vazdar, Ž. Marinić, M. Šindler-Kulyk, M. Eckert-Maksić and D. Margetić, Org. Biomol. Chem., 2011, 9, 6771
DOI: 10.1039/C1OB05802A

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