Formation of perfluorinated 1,2-dialkylbenzenes from perfluoroalkylbenzocyclobutenes in the system I2-SbF5

Gold-Catalyzed Simultaneous Formation of C–C, C═O, and C–F bonds in the Presence of Selectfluor: A Synthesis of Fluoroindenes from Allene Esters

“…Besides, some fluorinated indene derivatives, e.g., 1,1,6,7-tetrafluoroindanes, can be applied in material science as liquid crystal displaying materials. Regarding their preparation, in contrast to the rich chemistry of the preparation of indenes, ,,, efficient methods for the preparation of fluorinated indene derivatives remain quite limited. − Most of the existing methods for the synthesis of fluorinated indenes ,− suffer from one or more limitations with respect to multistep procedures, not easy availability of the starting materials, harsh reaction conditions, low chemo- or regioselectivity, and lack of generality. As such, it is still desirable to develop efficient approaches for the preparation of fluoroindenes from simple and readily available substrates.…”

Opening of the four-membered ring in perfluorinated 1-alkyl-2-phenyl- and 1-aryl-1,2-dihydrocyclobutabenzenes in the system I2-SbF5

“…A probable mechanism of opening of the fourmembered ring in polyfluorinated benzocyclobutenes by the action of I 2 -SbF 5 was discussed by us previously [4,5]. It was presumed that cleavage of the C 1 -C 2 bond occurs with participation of I 2 molecule although iodine in SbF 5 exists mainly as I 2 + species [11].…”

“…In contrast, opening of the four-membered ring in compound I in the system I 2 -SbF 5 occurs at both C arom -C 2 and C 1 -C 2 bonds, leading to 1,2,3,4-tetrafluoro-5-iodo-6-(perfluoroethyl)benzene together with perfluoro(o-xylene) (IV) [4]. However, no iodo derivatives were formed in analogous reactions of cyclobutabenzenes II and III, and the major products were the corresponding perfluoro(1,2-dialkylbenzenes) [5].With a view to elucidate how the nature of perfluorinated substituents in the four-membered ring of perfluorinated 1,2-dihydrocyclobutabenzenes affects …”