Oxidative Photocyclization of Tethered Bifluorenylidenes and Related Compounds

Abstract

Recent advances in fullerene chemistry have provoked an ever burgeoning interest in bowl-like polycyclic aromatic hydrocarbons.1-4 The key step used in the synthesis of these compounds involves either a pyrolytic or a photocatalyzed pericyclic process. Various circulenes are prepared by these methods.* 1 More recently, the

Photochemical Oxidative Cyclisation of Stilbenes and Stilbenoids—The Mallory-Reaction

“…I 2 , Methanol, hν = 21 h [ 70 ] 2 eq. I 2 , Benzene, hν = 8 h [ 71 ] Cat. I 2 , Benzene, hν = 24 h [ 72 ] 0.5 eq.…”

Facile Aromatization Reactions of Overcrowded Polycyclic Aromatic Enes Leading to Fullerene Fragments

“…The oxidative photocyclization of 1 to give 3 has also been claimed . However, the 1 H NMR data of the product was not consistent with those of 3 ( vide infra) . The synthesis of bridged derivatives of 3 by oxidative photocyclization reactions of ( Z )-2,2‘-tethered bifluorenylidenes have been reported by Luh et al .…”

An Efficient and Convenient Protocol for the Synthesis of 1,1-Difluoro-6-nitro-2,3-dihydro-1H-indene Derivatives

“…This method was more efficient than those described in the literature, which usually employed boron trifluoride-diethyl ether complex or aluminum trichloride. [20][21][22][23][24] To our surprise, treatment of dithioketal 9 with 1,3-dibromo-5,5-dimethylhydantoin and hydrogen fluoride-pyridine afforded only a trace amount of 13. Instead, the brominated derivative 10 was obtained as the major product in 88% yield.…”