1233344-84-7Relevant academic research and scientific papers
Thermal reaction of [3,4]-benzo-8-substituted-3Z,5Z,7E-octatetraenes and quantum-chemical study of the (8π,6π)-electrocyclisation
Skoric, Irena,Pavosevic, Fabijan,Vazdar, Mario,Marinic, Zeljko,Sindler-Kulyk, Marija,Eckert-Maksic, Mirjana,Margetic, Davor
, p. 6771 - 6778 (2011)
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.
Flow-photochemical synthesis of the functionalized benzobicyclo[3.2.1]octadiene skeleton
Ratkovi?, Ana,Marini?, ?eljko,?kori?, Irena
, p. 165 - 174 (2018/06/08)
A convenient practical home-made continuous flow-photochemistry setup was evaluated with the aim to enable a more efficient protocol for the synthesis of functionalized benzobicyclo[3.2.l]octadiene skeleton by intramolecular [2+2]-photocycloaddition react
