From fullerene-mixed peroxide to open-cage oxafulleroid C(59)(O)(3)(OH)(2)(OO(t)()Bu)(2) embedded with furan and lactone motifs.
[reaction: see text] Removal of one carbon atom from the C60 cage is achieved under mild conditions. The process involves the formation of fullerene-mixed peroxide, subsequent Lewis acid induced cleavage of O-O and C-O bonds, and thermolysis at 75 degrees C. In the proposed mechanism, the carbon atom is deleted as CO and an oxygen atom occupies the vacancy to form a furan ring. Single-crystal X-ray analysis confirmed the results.
Wang
Fudong
F
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Xiao
Zuo
Z
Gan
Liangbing
L
Jia
Zhenshan
Z
Jiang
Zhongping
Z
Zhang
Shiwei
S
Zheng
Bo
B
Gu
Yuan
Y
D018360:Crystallography, X-Ray; D037741:Fullerenes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010545:Peroxides / Q000737:chemistry*
D037741:Fullerenes; D005663:Furans; D007783:Lactones; D010545:Peroxides; C520148:oxafulleroid; C039281:furan