Formation of Singly Bonded PhCH<sub>2</sub>C<sub>60</sub>–C<sub>60</sub>CH<sub>2</sub>Ph Dimers from 1,2-(PhCH<sub>2</sub>)HC<sub>60</sub> via Electroreductive C<sub>60</sub>–H Activation
Wei-Wei Yang (1533976)Zong-Jun Li (1430323)Xiang Gao (4077)
Abstract
Singly bonded PhCH<sub>2</sub>C<sub>60</sub>–C<sub>60</sub>CH<sub>2</sub>Ph dimers are generated via controlled-potential bulk electroreduction and electrooxidation of 1,2-(PhCH<sub>2</sub>)HC<sub>60</sub>. The reaction mixture was purified by HPLC, and the isolated fraction was characterized with single-crystal X-ray diffractions, <sup>1</sup>H and <sup>13</sup>NMR, MS, elemental analysis, and cyclic voltammetry. It was shown that the fraction consists of two HPLC-inseparable PhCH<sub>2</sub>C<sub>60</sub>–C<sub>60</sub>CH<sub>2</sub>Ph regioisomers, which are assigned as the meso and racemic regioisomers. The bulk electrolysis processes for the formation of the dimers were followed by in situ cyclic voltammetry and were further corroborated with an in situ voltammetric titration of 1,2-(PhCH<sub>2</sub>)HC<sub>60</sub> with tetra-<i>n</i>-butylammonium hydroxide (TBAOH), on the basis of which a reaction mechanism is proposed.
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