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

Research output: Contribution to journalArticle

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 C3v symmetry.

Original languageEnglish
Pages (from-to)6075-6078
Number of pages4
JournalOrganic Letters
Volume8
Issue number26
DOIs
StatePublished - 21 Dec 2006

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