Switch of electronic reactivity in fullerene C60: Activation of three trans-4 positions via temporary saturation of the cis-1 positions

Shih-Ching Chuang; Saeed I. Khan; Yves Rubin

doi:10.1021/ol0625637

Switch of electronic reactivity in fullerene C₆₀: Activation of three trans-4 positions via temporary saturation of the cis-1 positions

Shih-Ching Chuang, Saeed I. Khan, Yves Rubin^*

^*Corresponding author for this work

Department of Applied Chemistry

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

7 Scopus citations

Abstract

(Chemical Equation Presented) The regioselective functionalization of C₆₀ with a trans-4,trans-4,trans-4 trisaddition pattern is not feasible directly. We have found an indirect approach taking advantage of the modified electronic reactivity of cis-1 bisadducts. The cis-1 addition pattern electronically activates three trans-4 C=C bonds on the opposite hemisphere of C₆₀, allowing further highly regioselective additions at these positions. Thermal removal of the cis-1 blocking unit results in a trans-4,trans-4,trans-4 trisadduct with C_3v symmetry.

Original language	English
Pages (from-to)	6075-6078
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	26
DOIs	https://doi.org/10.1021/ol0625637
State	Published - 1 Dec 2006

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abstract = "(Chemical Equation Presented) The regioselective functionalization of C60 with a trans-4,trans-4,trans-4 trisaddition pattern is not feasible directly. We have found an indirect approach taking advantage of the modified electronic reactivity of cis-1 bisadducts. The cis-1 addition pattern electronically activates three trans-4 C=C bonds on the opposite hemisphere of C60, allowing further highly regioselective additions at these positions. Thermal removal of the cis-1 blocking unit results in a trans-4,trans-4,trans-4 trisadduct with C3v symmetry.",

author = "Shih-Ching Chuang and Khan, {Saeed I.} and Yves Rubin",

year = "2006",

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T2 - Activation of three trans-4 positions via temporary saturation of the cis-1 positions

AU - Chuang, Shih-Ching

AU - Khan, Saeed I.

AU - Rubin, Yves

PY - 2006/12/1

Y1 - 2006/12/1

N2 - (Chemical Equation Presented) The regioselective functionalization of C60 with a trans-4,trans-4,trans-4 trisaddition pattern is not feasible directly. We have found an indirect approach taking advantage of the modified electronic reactivity of cis-1 bisadducts. The cis-1 addition pattern electronically activates three trans-4 C=C bonds on the opposite hemisphere of C60, allowing further highly regioselective additions at these positions. Thermal removal of the cis-1 blocking unit results in a trans-4,trans-4,trans-4 trisadduct with C3v symmetry.

AB - (Chemical Equation Presented) The regioselective functionalization of C60 with a trans-4,trans-4,trans-4 trisaddition pattern is not feasible directly. We have found an indirect approach taking advantage of the modified electronic reactivity of cis-1 bisadducts. The cis-1 addition pattern electronically activates three trans-4 C=C bonds on the opposite hemisphere of C60, allowing further highly regioselective additions at these positions. Thermal removal of the cis-1 blocking unit results in a trans-4,trans-4,trans-4 trisadduct with C3v symmetry.

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 26

ER -

Switch of electronic reactivity in fullerene C₆₀: Activation of three trans-4 positions via temporary saturation of the cis-1 positions

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