Xiao, Zuo Yao, Jiayao Yang, Dazhi Wang, Fudong Huang, Shaohua Gan, Liangbing Jia, Zhenshan Jiang, Zhongping Yang, Xiaobing Zheng, Bo Yuan, Gu Zhang, Shiwei Wang, Zheming Synthesis of [59]Fullerenones through Peroxide-Mediated Stepwise Cleavage of Fullerene Skeleton Bonds and X-ray Structures of Their Water-Encapsulated Open-Cage Complexes Fullerene skeleton modification has been investigated through selective cleavage of the fullerene carbon−carbon bonds under mild conditions. Several cage-opened fullerene derivatives including three [59]fullerenones with an 18-membered-ring orifice and one [59]fullerenone with a 19-membered-ring orifice have been prepared starting from the fullerene mixed peroxide <b>1</b>, C<sub>60</sub>(OO<sup>t</sup>Bu)<sub>6</sub>. The prepositioned <i>tert</i>-butyl peroxy groups in <b>1</b> serve as excellent oxygen sources for formation of hydroxyl and carbonyl groups. The cage-opening reactions were initiated by photoinduced homolysis of the <sup>t</sup>Bu−O bond, followed by sequential ring expansion steps. A key step of the ring expansion reactions is the oxidation of adjacent fullerene hydroxyl and amino groups by diacetoxyliodobenzene (DIB). Aminolysis of a cage-opened fullerene derivative containing an anhydride moiety resulted in multiple bond cleavage in one step. A domino mechanism was proposed for this reaction. Decarboxylation led to elimination of one carbon atom from the C<sub>60</sub> cage and formation of [59]fullerenones. The cage-opened [59]fullerenones were found to encapsulate water under mild conditions. All compounds were characterized by spectroscopic data. Single-crystal structures were also obtained for five skeleton-modified derivatives including two water-encapsulated fulleroids. sequential ring expansion steps;anhydride moiety;orifice;photoinduced homolysis;carbon atom;oxygen sources;ring expansion reactions;fullerenone;formation;domino mechanism;bond cleavage;spectroscopic data;fullerene hydroxyl;C 60 cage;derivative;carbonyl groups;DIB;Fullerene Skeleton Bonds 2007-12-26
    https://acs.figshare.com/articles/dataset/Synthesis_of_59_Fullerenones_through_Peroxide_Mediated_Stepwise_Cleavage_of_Fullerene_Skeleton_Bonds_and_X_ray_Structures_of_Their_Water_Encapsulated_Open_Cage_Complexes/2966503
10.1021/ja0763798.s004