Reaction of octafluorocyclopentene with various carbon nucleophiles

Mechanistic investigation of vinylic carbon–fluorine bond activation of perfluorinated cycloalkenes using Cp*2ZrH2 and Cp*2ZrHF

“…A similar mechanism has been proposed in the reactions of Cp* 2 ZrH 2 with monofluoroarenes [19]. Other nucleophiles such as aryl and heteroaryl [31], alkyl [32], alkenyl [33], alkynyl [34], alkoxides, mercaptans, and amines [35] are well known to react with perfluorinated cyclic olefins to give substitution products by the same mechanism. These perfluorocycloolefins are highly toxic (similar to phosgene) as a result of their susceptibility to reactions with biological nucleophiles [36].…”

1,2‐Disubstituted 3,3,4,4,5,5‐Hexafluorocyclopentenes as Bent Light‐Emitting π‐Conjugated Luminophores

“…Based on our preliminary theoretical calculations, we next carried out the synthesis of bent π‐conjugated molecules 1 . Among the target molecules, we have already accomplished the syntheses of 1a – c and reported the synthetic procedures (Scheme ) Based on these reported procedures, we investigated the syntheses of the other analogues 1d – i .…”

“…In conclusion, we synthesized a series of 1,2‐disubstituted 3,3,4,4,5,5‐hexafluorocyclopentenes 1d – i according to our previously reported synthetic procedures, and their photophysical properties were evaluated in detail. 1b – i bearing 2‐arylethyn‐1‐yl arms were found to display PL, for which the PL maximum wavelength ( λ PL ) and PL color changed in accordance with differences in the electronic properties of the terminal substituents.…”

Helicenes Fused with Hexafluorocyclopentene (HFCP): Synthesis, Structure, and Properties

“…Schemeà displays the synthetic route to these compounds. Treatment of OFCP with an aryllithium yields the corresponding diarylethene intermediate via an addition‐elimination reaction . A Mallory reaction of the diarylethene affords the HFCP‐PAH in moderate to good yield.…”