Fused-Pentagon Carbon Cages in Chloro and Trifluoromethyl Derivatives of C 60 : Non-IPR 1809 C 60 Cl 8 , 1806 C 60 (CF 3 ) 14 , and Nonclassical C 60 ( NC )Cl 14 .

High-temperature chlorination of conventional IPR C 60 can produce chloro derivatives of non-IPR C 60 by skeletal transformations via Stone-Wales rearrangements (SWRs) of the carbon cage. We report the synthesis and structure elucidation of non-IPR 1809 C 60 Cl 8 and nonclassical C 60 ( NC )Cl 14 . The present isolation of 1809 C 60 Cl 8 hints at the possibility that the same product in the previously reported chlorine-doped arc-discharge synthesis could have, likewise, resulted from the initially formed IPR C 60 . C 60 ( NC )Cl 14 is the first chloride containing a nonclassical carbon cage with one heptagon and 13 pentagons known previously only in a CF 3 derivative. Additionally, trifluoromethylation of non-IPR chlorides revealed the formation of 1806 C 60 (CF 3 ) 14 with a new non-IPR carbon cage and unusual trifluoromethylation pattern. Thereby, the number of different, structurally confirmed non-IPR carbon cages of C 60 now reaches eight.