Synthesis of oxazolidinofullerenes/thiazolidinofullerenes: novel reaction of [60]fullerene with isocyanates/isothiocyanates promoted by ferric perchlorate

Abstract

The facile one-step reaction of [60]fullerene with isocyanates/isothiocyanates in the presence of ferric perchlorate generates a series of novel oxazolidinofullerenes/thiazolidinofullerenes.

Synthesis of Fullerene-Fused Dioxanes/Dioxepanes: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Diols

“…Recently, transition-metal-salt-mediated radical reactions of fullerenes have attracted tremendous attention . Diverse types of transition metal salts such as those of Mn, Fe, ,,, W, Cu, Pb, Co, and Ag have been utilized as the promoters to functionalize fullerenes. Compared with the traditional peroxide- or light-initiated processes, the radical reactions of fullerenes promoted by transition metal salts could proceed well under mild conditions and tend to give a monoaddition product that is relatively easy to isolate and purify, through which numerous novel monoaddition fullerene derivatives have been prepared.…”

Dithiolation of [70]Fullerene with Aliphatic Primary Thiols in the Presence of n-Butylamine via Aerobic Oxidation Reaction

“…Notably, thiolation of fullerenes have shown some important impacts on the derivatives such as the case of open-cage fullerenes, where an expansion of the orifices and thiafullerenes with one sulfur atom incorporated into the carbon skeleton are resulted . Currently, the formation of the C 2 n –S ( n = 30, 35) bonds is mainly achieved with reagents including thioacrylamides, benzothiet, thiadiazolidinones, dendrimer disulfide, 1,4-dithiane-2,5-diol, aryl isothiocyanates, , sulfur, and CS 2 , where an intramolecular nucleophilic addition of the in situ generated thiols to C 60 is observed during the reaction of C 60 with 1,4-dithiane-2,5-diol and N -methylglycine, affording the cis -1 bicyclic-fused fullerene derivative . As for thiolation with thiols, it is typically achieved via an indirect manner by reacting with multiple chlorinated fullerenes (C 60 Cl 6 or C 70 Cl 10 ) rather than pristine fullerenes, with the production of pentathiolated fullerene derivatives (C 2 n (SR) 5 H, n = 30 or 35) .…”

Copper-Catalyzed Aerobic Oxidative Reaction of C60 with Aliphatic Primary Amines and CS2

“…Because of the unique electronic and three-dimensional structure of fullerenes, the chemistry of fullerenes has attracted great interest during the last several decades, with the development of a great number of reactions and fullerene derivatives, , which have shown potentials in areas such as materials science and medicinal chemistry . However, progress on fullerene thiolation is rather slow, where sophisticated reagents such as isothiocyanate and thiadiazolidinone are usually required, − whereas the simple and common reagent of CS 2 is rarely used . It is noteworthy that CS 2 is an excellent solvent for fullerenes, which has strong interaction with fullerenes as shown in the crystalline fullerene/CS 2 solvates …”