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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)


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


Projekt / tema
098-0982929-2917 - Spektroskopija NMR i modeliranje bioaktivnih molekula (Dejan Plavšić, )
098-0982933-2920 - Organski i bioorganski procesi u osnovnom i elektronski pobuđenim stanjima (Mirjana Maksić, )
098-0982933-3218 - 'Host-guest' međudjelovanja u policikličkim sustavima (Davor Margetić, )
125-0982933-2926 - Heteropolicikli, strukturne osnove za bioaktivne spojeve. Sinteza i fotokemija (Irena Škorić, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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