Synthesis and reactivity of tetraalkoxyl[60]fullerene epoxides, C₆₀(O)(OR)₄

Abstract

Hexachloro[60]fullerene, C60Cl6, was reacted with a mixture of ROH/H2O (R = Me, Et, n-Pr, (CH2)2C≡CH) to form both C60Cl(OH)(OR)4 and C60Cl(OR)5. Only the C60Cl(OH)(OR)4 were isolated with bulky alcohols, ROH (R = (CH2)3C≡CH, (CH2)4C≡CH). Tetrahydro[60]fullerene epoxides, C60(O)(OR)4, were prepared by treating C60Cl(OH)(OR)4 with CuI. The epoxy moiety could be hydrolyzed to the vicinal diol derivatives, C60(OH)2(OR)4, and then oxidized to form dicarbonyl open-cage fullerenes, C60O2(OR)4. CuI was found to convert the terminal alkynyl addends into iodoalkynyl addends on the C60 cage.

Fullerene Stabilizer 4,11,15,30-Tetraarylamino Fullerenoarylaziridine: Regioselective Synthesis, Crystallographic Characterization Derivatives, and Potential Application as Propellant Stabilizer

“…Although the complete fullerene molecular structure is relatively stable with strong capacity for absorbing free radicals, the rate of “capture” to free radicals is low. − Functional fullerene derivative can substantially increase the rate of “capture” to free radicals, which ascribed to the modification of functional groups to destroy the conjugated structure of fullerenes. − C 60 Cl 6 is a widespread precursor for the synthesis of highly functionalized fullerene derivatives. − Many different nucleophiles can replace the chlorine atoms in C 60 Cl 6 to form multifunctional fullerene derivatives. − In this study, C 60 Cl 6 as a precursor was applied to synthesize multifunctional fullerene derivatives via the reaction with aromatic amines (Scheme ), and its possibility as a propellant stabilizer was studied. We first explored the reactions of C 60 Cl 6 and aniline 1a .…”

[60]Fullerene‐Based Macrocycle Ligands

“…Insertion of sulfur, oxygen and nitrogen has been achieved on the rim of the orifice as in compounds 19 – 23 (Scheme ) . We have reported a number of open‐cage fullerene derivatives . Most of the known open‐cage fullerene derivatives are not suitable ligands for metal ions due to the unfavorable orientation and arrangement of the functional groups on the rim of their orifices.…”

“…[20][21] We have reported anumber of open-cage fullerene derivatives. [22] Most of the known open-cage fullerene derivatives are not suitable ligandsf or metal ions due to the Scheme6.Selectivep entasubstitution of corannulene reported by Scott.…”