87771-75-3Relevant academic research and scientific papers
Fluorinated Phenanthrenes as Aryne Precursors: PAH Synthesis Based on Domino Ring Assembly Using 1,1-Difluoroallenes
Abe, Masashi,Fuchibe, Kohei,Ichikawa, Junji,Idate, Hiroto
, (2020)
On treatment with the catalyst InBr3, 1,1-difluoroallenes that bear a cyclopentene moiety and an aryl group underwent domino ring assembly in the presence or absence of N-bromosuccinimide or N-iodosuccinimide to afford aryne precursors such as three-ringed ortho-fluoro(halo)phenanthrenes, four-ringed ortho-fluoro(halo)tetraphenes, ortho-fluoro(halo)chrysenes and fluoro[4]helicenes. Metalation of the aryne precursors followed by elimination of the fluoride resulted in the unprecedented systematic generation of arynes bearing π-extended systems. Diels?Alder reactions of these arynes with isobenzofurans afforded the corresponding cycloadducts whose reductive aromatisation in an SnCl2/HBr system furnished fully aromatised benzotriphenylenes. In addition, oxidative aryl?aryl coupling (the Scholl reaction) of these benzotriphenylenes facilitated the synthesis of ‘half HBCs’ (hexabenzocoronenes).
Polycyclic Aromatic Compounds: Part VIII - A New Synthesis of Polycyclics Containing Phenanthrene Nucleus
Mondal, S.,Bandyopadhyay, T. K.,Bhattacharya, A. J.
, p. 448 - 452 (2007/10/02)
A new series of polycyclic aromatic compounds with phenanthrene nucleus have been prepared.The method involves Diels Alder cycloaddition reaction of 1,3-diaryl-2H-cyclopentaphenanthren-2-one (I) with various dienophiles, viz. bicyclohepta-2,5-di
