《Fluorinated Phenanthrenes as Aryne Precursors: PAH Synthesis Based on Domino Ring Assembly Using 1,1-Difluoroallenes》 was written by Fuchibe, Kohei; Abe, Masashi; Idate, Hiroto; Ichikawa, Junji. Synthetic Route of C20H14O And the article was included in Chemistry – An Asian Journal in 2020. The article conveys some information:
On treatment with the catalyst InBr3, 1,1-difluoroallenes e.g., [1-(3,3-difluoropropa-1,2-dien-1-yl)cyclopent-3-en-1-yl]benzene 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 6-fluoro-benzo[c]phenanthrene. Metalation of the aryne precursors followed by elimination of the fluoride resulted in the unprecedented systematic generation of arynes bearing π-extended systems e.g., 9,14-dihydro-9,14-diphenyl-9,14-epoxybenzo[b]triphenylene. Diels-Alder reactions of these arynes with isobenzofurans afforded the corresponding cycloadducts e.g., I, whose reductive aromatization in an SnCl2/HBr system furnished fully aromatized benzotriphenylenes e.g., 9,14-diphenylbenzo[b]triphenylene. In addition, oxidative aryl-aryl coupling (Scholl reaction) of these benzotriphenylenes facilitated the synthesis of ‘half HBCs’ (hexabenzocoronenes) II (R1 = H, n-Hex, t-Bu). In addition to this study using 1,3-Diphenylisobenzofuran, there are many other studies that have used 1,3-Diphenylisobenzofuran(cas: 5471-63-6Synthetic Route of C20H14O) was used in this study.
1,3-Diphenylisobenzofuran(cas: 5471-63-6) can be used as a fluorescent probe for detection of superoxide anion radical (O2−) inside the membrane lipid layer by DPBF fluorescence quenching method. 1,3-Diphenylisobenzofuran(DPBF) can be used as quencher during the photoinactivation of TA-3 mouse mammary carcinoma cells containing hematoporphyrin.Synthetic Route of C20H14O
Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem