Pentafluorophenyl Transfer Reaction: Preparation of Pentafluorophenyl [60]Fullerene Adducts through Opening of Fullerene Epoxide Moiety with Trispentafluorophenylborane

Abstract

Unlike the extensively studied perfluoroalkyl fullerene adducts, perfluorophenyl fullerene adducts are quite difficult to prepare by known methods. Trispentafluorophenylborane was found to react with fullerene epoxide to form the 1,2-perfluorophenylfullerenol. The method can be applied to both the simple epoxide C60(O) and fullerene multiadducts containing an epoxide moiety. Single crystal X-ray structure analysis confirmed the addition of the pentafluorophenyl group.

Hypervalent Iodine Reagent Mediated Diamination of [60]Fullerene with Sulfamides or Phosphoryl Diamides

“…Chemical modification on the sphere of C 60 allows the preparation of large quantities of fullerene derivatives with different structures and properties for the investigation of their application in biological and material science. Until now, a variety of methods for chemical functionalization of fullerenes have been explored involving various [2 + n ] ( n = 1–4) reactions, redox reactions, cycloadditions, radical additions, nuclophilic additions, and multiadditions . Free-radical reactions were one of the most investigated reactions in fullerene chemistry and continue to be an effective strategy for the functionalization of fullerenes.…”

Synthesis and Chemical Reactivity of Tetrahydro[60]fullerene Epoxides with Both Amino and Aryl Addends

“…Treatment of 6 with ferric chloride in toluene afforded the hexaadduct 7 with the addition of another tolyl addend. 15b, 17 Hydroxyl and alkoxyl groups were added by using ptoluenesulfonic acid as the catalyst. The epoxide opening reactions are highly regioselective, producing only the product with the hydroxyl group on the central pentagon.…”

“…Indeed, introduction of aryl groups improves the selectivity and results in reactions analogous to those for the tetraperoxo C 60 epoxide C 60 (O)­(OO t Bu) 4 . Treatment of 6 with ferric chloride in toluene afforded the hexaadduct 7 with the addition of another tolyl addend. , Hydroxyl and alkoxyl groups were added by using p -toluenesulfonic acid as the catalyst. The epoxide opening reactions are highly regioselective, producing only the product with the hydroxyl group on the central pentagon .…”

Highly efficient synthesis of [60]fullerene oxides by plasma jet

“…In addition, the formation of C 60 O and C 60 O n (n ≥ 2) was identified by mass spectroscopy or high-performance liquid chromatography (HPLC), yet no isolated yields were reported in the oxidation of electrochemically generated anionic C 60 [15] and ozonolysis of C 60 [16][17][18]. Interestingly, C 60 O has been employed as the precursor for further functionalizations, leading to the formation of C 120 O [19], 1,3-dioxolane derivatives of C 60 [20], indoline derivatives of C 60 [21], and 1,2-perfluorophenylfullerenol [22]. Similarly, the cis-1 isomer of C 60 O 2 has been used as the precursor for bis-1,3-dioxolane derivatives of C 60 [20].…”