Preparation of fullerendione through oxidation of vicinal fullerendiol and intramolecular coupling of the dione to form hemiketal/ketal moieties.
[reaction: see text] Vicinal fullerendiol is oxidized to fullerendione in good yield by (diacetoxy)iodobenzene. The resulting cage-opened fullerendione reacts with oxygen nucleophiles in the presence of BF(3).Et(2)O to form fullerene hemiketal/ketal derivatives through coupling of the two carbonyl groups. Fullerene-mixed peroxide derivatives are involved in all these reactions. The compounds are characterized by spectroscopic data and single-crystal X-ray analysis.
Huang
Shaohua
S
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, China.
Wang
Fudong
F
Gan
Liangbing
L
Yuan
Gu
G
Zhou
Jiang
J
Zhang
Shiwei
S