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Chlorination‐Promoted Cage Transformation of IPR C 92 Discovered via Trifluoromethylation under Formation of Non‐classical C 92 ( NC )(CF 3 ) 22
Author(s) -
Tamm Nadezhda B.,
Guan Runnan,
Yang Shangfeng,
Kemnitz Erhard,
Troyanov Sergey I.
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900469
Subject(s) - trifluoromethylation , chemistry , fullerene , derivative (finance) , medicinal chemistry , cage , chloride , stereochemistry , organic chemistry , financial economics , alkyl , trifluoromethyl , economics , mathematics , combinatorics
High‐temperature trifluoromethylation of isolated‐pentagon‐rule (IPR) fullerene C 92 chlorination products followed by HPLC separation of C 92 (CF 3 ) n derivatives resulted in the isolation and X‐ray structural characterization of IPR C 92 (38)(CF 3 ) 18 and non‐classical C 92 ( NC )(CF 3 ) 22 . The formation of C 92 (38)(CF 3 ) 18 as the highest CF 3 derivative of the known isomer C 92 (38) can be expected. The formation of C 92 ( NC )(CF 3 ) 22 was interpreted as chlorination‐promoted cage transformation of C 92 (38) followed by trifluoromethylation of non‐classical C 92 ( NC ) chloride. Noticeably, C 92 ( NC )(CF 3 ) 22 shows the highest degree of trifluoromethylation among all known CF 3 derivatives of fullerenes. The addition patterns of C 92 (38)(CF 3 ) 18 and C 92 ( NC )(CF 3 ) 22 are discussed and compared to the chlorination patterns of C 92 (38)Cl n compounds.