A Protocol for the Preparation of 2,5-Diaryl Fulleropyrrolidines: Thermal Reaction of [60]Fullerene with Aromatic Aldehydes and Arylmethanamines.
J Org Chem
; 81(17): 7662-74, 2016 09 02.
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| MEDLINE
| ID: mdl-27471871
ABSTRACT
Thermal reaction of [60]fullerene with various arylmethanamines in the presence of aromatic aldehydes under air conditions afforded a series of rare 2,5-diaryl fulleropyrrolidines. Intriguingly, the obtained fulleropyrrolidines exhibited different stereoselectivity. N-unsubstituted arylmethanamines exclusively produced 2,5-diaryl fulleropyrrolidines as cis isomers, while N-substituted arylmethanamines with rare exceptions always gave 2,5-diaryl fulleropyrrolidines as trans isomers. Theoretical calculations at the level of B3LYP/6-31G (d,p) were employed to elucidate the stereoselectivity of N-substituted 2,5-diaryl fulleropyrrolidines as trans isomers by investigating the transition-state structures of different cycloaddition pathways.
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2016
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Article