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Preparation of Ketolactone and Bislactone [60]Fullerene Derivatives and Their Conversion into Open‐Cage Fullerenes with a 12‐ or 15‐Membered Orifice
Author(s) -
Zhang Jianxin,
Wang Fudong,
Xin Nana,
Yang Dazhi,
Gan Liangbing
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100777
Subject(s) - chemistry , moiety , fullerene , epoxide , stereochemistry , lactone , thermal decomposition , medicinal chemistry , catalysis , organic chemistry
Selective cleavage of the peroxo group in the fullerene mixed peroxide C 60 (O)(OO t Bu) 6 1 produces open‐cage fullerenes with ketone and lactone moieties on the rim of the orifice. Photolysis of 1 results in the ketolactone derivative 2 C 58 (CO)‐(COO)(O)(OO t Bu) 4 with an epoxide moiety. Thermolysis of 1 results in the formation of two other isomers, the bislactone 3 C 58 (COO) 2 (OO t Bu) 4 and the ketolactone 4 C 58 (CO)(COO)(O)(OO t Bu) 4 with a 1,4‐dioxepin‐5‐one moiety. Both alcohols and amines react with one of the lactone moieties of 3 and expand the 12‐membered orifice into a 15‐membered orifice. Only amines react with the lactone moiety of 4 and expand the 11‐membered orifice into a 12‐membered orifice. Total yield of the 15‐membered open‐cage compound can reach 8.9 % in three steps starting from C 60 . The products were characterized by spectroscopic data and X‐ray diffraction data.