From fullerene-mixed peroxide to open-cage oxafulleroid C(59)(O)(3)(OH)(2)(OO(t)()Bu)(2) embedded with furan and lactone motifs

Fudong Wang; Zuo Xiao; Liangbing Gan; Zhenshan Jia; Zhongping Jiang; Shiwei Zhang; Bo Zheng; Yuan Gu

doi:10.1021/ol070386j

From fullerene-mixed peroxide to open-cage oxafulleroid C(59)(O)(3)(OH)(2)(OO(t)()Bu)(2) embedded with furan and lactone motifs

Org Lett. 2007 Apr 26;9(9):1741-3. doi: 10.1021/ol070386j. Epub 2007 Mar 31.

Authors

Fudong Wang¹, Zuo Xiao, Liangbing Gan, Zhenshan Jia, Zhongping Jiang, Shiwei Zhang, Bo Zheng, Yuan Gu

Affiliation

¹ 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.

PMID: 17397174
DOI: 10.1021/ol070386j

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Fullerenes / chemistry*
Furans / chemistry*
Lactones / chemistry*
Models, Molecular
Molecular Structure
Peroxides / chemistry*

Substances

Fullerenes
Furans
Lactones
Peroxides
oxafulleroid
furan