Thermal reaction of [3,4]-benzo-8-substituted-3Z,5Z,7E-octatetraenes and quantum-chemical study of the (8π,6π)-electrocyclisation (CROSBI ID 159833)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Škorić, Irena ; Pavošević, Fabijan ; Vazdar, Mario ; Marinić, Željko ; Šindler-Kulyk, Marija ; Eckert-Maksić, Mirjana ; Margetić, Davor
engleski
Thermal reaction of [3,4]-benzo-8-substituted-3Z,5Z,7E-octatetraenes and quantum-chemical study of the (8π,6π)-electrocyclisation
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.
pericyclic reactions ; electrocyclisation ; octatetraenes ; reaction mechanism ; quantumchemical
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
Podaci o izdanju
9 (19)
2011.
6771-6778
objavljeno
1477-0520
1477-0539
10.1039/c1ob05802a