Carving two adjacent holes on [60]fullerene through two consecutive epoxide to diol to dione transformations

Abstract

Repeated acid catalyzed epoxide opening and oxidation of the resulting diol with diacetoxyiodobenzene led to two 10-membered orifices on C(60) cage.

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

“…Presence of the hemiketal hydroxyl group has little effect judging from the comparable yields of 3 and 5 . But the B(C 6 F 5 ) 3 catalyzed hydrolysis of compound 4 followed a S N 2′ type mechanism to form compound 6 as shown previously . The color of 6 is dark brown, whereas the color of both 4 and 5 is orange.…”

Peroxide‐Mediated Selective Cleavage of [60]Fullerene Skeleton Bonds: Towards the Synthesis of Open‐Cage Fulleroid C55O5

“…The distances between the two carbonyl oxygen atoms and the two carbon atoms are 2.581 and 2.636 Å, respectively. The DIB oxidation could be extended to analogous fullerene derivatives with a diol moiety to form open‐cage compounds such as 7 , 8 and 9 . Treatment of 1 with PPh 3 /I 2 gave the ketolactone compound 9 in one step.…”

Double-Holed Fullerenes

“…Before our trials, the groups of Rubin and Gan independently reported two examples characterized spectroscopically that were obtained via multiple reactions using well-designed precursors, albeit low yielding. Our synthetic strategy is a one-pot two-fold cage-opening process that commences with the Diels–Alder reaction of C 60 and azine derivatives to afford cage-opened derivative 1 , (Figure a).…”