Organic Letters 2018-04-10

Controlled Synthesis of C70 Equatorial Multiadducts with Mixed Addends from an Equatorial Diadduct: Evidence for an Electrophilic Carbanion

Shu-Hui Li, Zong-Jun Li, Wei-Wei Yang, Xiang Gao

Index: 10.1021/acs.orglett.8b00672

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Abstract

Controlled synthesis of the equatorial tetra-, hexa-, and octaorgano[70]fullerenes with mixed addends was achieved via the reaction of equatorial 7,23-Bn2C70 with MeO– and ArCH2Br. The products were structurally characterized by single crystal X-ray diffraction. The regioselectivity of the reaction was studied by in situ vis–NIR and Fukui function analysis. A surprising electrophilic triorgano[70]fullerene carbanion was shown, and an enhanced fluorescence was observed for the mixed octaadducts.