Abstract
AbstractThermally‐induced CF2 addition to Cs‐C70(CF3)8 upon reaction with sodium chlorodifluoroacetate is found to proceed via the nucleophilic cyclopropanation pathway, possibly with a certain involvement of the alternative singlet carbene pathway. Of the two major isomers of C70(CF3)8(CF2) characterized by X‐ray diffraction and spectroscopically, the less abundant one has a [6,6]‐open structure whereas the more abundant product is a [5,6]‐open isomer with highly reactive bridgehead sites. Under ambient conditions, its rapid oxidation and hydration produce C70(CF3)8[CF2](OH)2 and C70(CF3)8[CF2](OH)H, respectively, in which the π‐system is split in two disjoint caps and the HOMO–LUMO gap is considerably increased, as evidenced by the blue‐shifted fluorescence.
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