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

doi:10.1039/c1ob05802a

Pregled bibliografske jedinice broj: 448896

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

Thermal reaction of [3,4]-benzo-8-substituted-3Z,5Z,7E-octatetraenes and quantum-chemical study of the (8π,6π)-electrocyclisation // Organic & biomolecular chemistry, 9 (2011), 19; 6771-6778 doi:10.1039/c1ob05802a (međunarodna recenzija, članak, znanstveni)

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

Autori
Škorić, Irena ; Pavošević, Fabijan ; Vazdar, Mario ; Marinić, Željko ; Šindler-Kulyk, Marija ; Eckert-Maksić, Mirjana ; Margetić, Davor

Izvornik
Organic & biomolecular chemistry (1477-0520) 9 (2011), 19; 6771-6778

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
pericyclic reactions ; electrocyclisation ; octatetraenes ; reaction mechanism ; quantumchemical

Sažetak
The first example of thermal (8π, 6π)- electrocyclisation of 1, 3, 5, 7-octatetraene with one double bond embedded in 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 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA

Projekti:
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MZOS-098-0982933-3218 - Host-guest međudjelovanja u policikličkim sustavima (Margetić, Davor, MZOS ) ( CroRIS)
MZOS-125-0982933-2926 - Heteropolicikli, strukturne osnove za bioaktivne spojeve. Sinteza i fotokemija (Škorić, Irena, MZOS ) ( CroRIS)