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Unexpected Reactions of [60]Fullerene Involving Tertiary Amines and Insight into the Reaction Mechanisms
Author(s) -
Wang GuanWu,
Chen XiaoPing,
Cheng Xin
Publication year - 2006
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.200600575
Subject(s) - triethylamine , chemistry , moiety , tertiary amine , bond cleavage , cleavage (geology) , stereoselectivity , fullerene , tertiary alcohols , medicinal chemistry , organic chemistry , catalysis , materials science , fracture (geology) , composite material
Thermal reactions of [60]fullerene with amino acid ester hydrochlorides and triethylamine in o ‐dichlorobenzene at reflux afforded pyrrolidinofullerene derivatives containing the CH 3 CH moiety and originating from triethylamine through an unusual CN bond cleavage. Detailed investigation of these thermal reactions resulted in the discovery of unprecedented reactions between C 60 and tertiary amines and of reactions of C 60 with tertiary amines and aldehydes, giving cyclopentafullerene derivatives with high stereoselectivity. Plausible reaction mechanisms for the product formation involving the uncommon CN bond cleavage of tertiary amines were proposed on the basis of extensive experimental results.