Facile Multiple Alkylations of C60 Fullerene

Abstract

The reduction of fullerene (C60) with sodium dispersion in the presence of an excess amount of dipropyl sulfate was found to yield highly propylated fullerene, C60(nC3H7)n (max. n = 24), and C60(nC3H7)20 was predominantly generated as determined by mass spectroscopy.

Multiply exo‐Methylated Corannulenes

“…[33] This reductive transformation was then used for multiple alkylations of spherical C 60 fullerene using dialkyl sulfate. [36] Our reductive alkylation is distinct from the conventional method which involves multi-reduction of C 60 to yield high-energy multi-anions of C 60 (C 60 nÀ ) followed by an addition of alkyl halide. [37][38][39][40] Instead, we reduced C 60 and its alkylated derivatives with sodium dispersion, [35] followed by insitu efficient and rapid trapping with the co-existing reductionresistant dialkyl sulfate.…”

“…Recently, we reported a sodium‐promoted reductive boration of planar PAHs using trialkoxyborane as an electrophile [33] . This reductive transformation was then used for multiple alkylations of spherical C 60 fullerene using dialkyl sulfate [36] . Our reductive alkylation is distinct from the conventional method which involves multi‐reduction of C 60 to yield high‐energy multi‐anions of C 60 (C 60 n − ) followed by an addition of alkyl halide [37–40] .…”