From fullerene-mixed peroxide to open-cage oxafulleroid C 59(O)3(OH)2(OOtBu)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^tBu)₂ embedded with furan and lactone motifs

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

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

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°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.

Original language	English (US)
Pages (from-to)	1741-1743
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	9
DOIs	https://doi.org/10.1021/ol070386j
State	Published - Apr 26 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "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°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.",

author = "Fudong Wang and Zuo Xiao and Liangbing Gan and Zhenshan Jia and Zhongping Jiang and Shiwei Zhang and Bo Zheng and Yuan Gu",

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T1 - From fullerene-mixed peroxide to open-cage oxafulleroid C 59(O)3(OH)2(OOtBu)2 embedded with furan and lactone motifs

AU - Wang, Fudong

AU - Xiao, Zuo

AU - Gan, Liangbing

AU - Jia, Zhenshan

AU - Jiang, Zhongping

AU - Zhang, Shiwei

AU - Zheng, Bo

AU - Gu, Yuan

PY - 2007/4/26

Y1 - 2007/4/26

N2 - 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°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.

AB - 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°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.

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JO - Organic Letters

JF - Organic Letters

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ER -

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

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