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PCy 3 ‐Catalyzed Ring Expansion of Aziridinofullerenes with CO 2 and Aryl Isocyanates: Evidence for a Two Consecutive Nucleophilic Substitution Pathway on the Fullerene Cage
Author(s) -
Takeda Youhei,
Kawai Hajime,
Minakata Satoshi
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301617
Subject(s) - fullerene , aryl , aziridine , chemistry , ring (chemistry) , catalysis , salt (chemistry) , combinatorial chemistry , phosphonium , medicinal chemistry , nucleophile , nucleophilic substitution , polymer chemistry , organic chemistry , alkyl
A PCy 3 ‐catalyzed ring‐expansion reaction of aziridine‐fused fullerenes (aziridinofullerenes) through the insertion of CO 2 and aryl isocyanates is disclosed. The reaction allows for CO 2 fixation by aziridinofullerenes, producing oxazolidinone‐fused fullerenes (oxazolidinofullerenes) in high yields, whereas treatment with aryl isocyanates led to a new fullerene family—imidazolidinone‐fused fullerenes (imidazolidinofullerenes)—in good to high yields. Furthermore, a mechanistically related unprecedented fullerenyl phosphonium salt was successfully isolated. Using the isolated salt, mechanistic studies were also investigated.