Unexpected reactions of [60]fullerene involving tertiary amines and insight into the reaction mechanisms.
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 C-N 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 C-N bond cleavage of tertiary amines were proposed on the basis of extensive experimental results.
Wang
Guan-Wu
GW
Hefei National Laboratory for Physical Sciences at Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China. gwang@ustc.edu.cn
Chen
Xiao-Ping
XP
Cheng
Xin
X
D000588:Amines / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry; D037741:Fullerenes / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry
D000588:Amines; D005021:Ethylamines; D037741:Fullerenes; D011759:Pyrrolidines; C069837:fullerene C60; C016162:triethylamine