Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Synthesis of 2-Aryl-5-alkyl-fulleropyrrolidines: Metal-Free-Mediated Reaction of [60]Fullerene with Aromatic Aldehydes and Inactive Primary Amines

Synthesis of 2-Aryl-5-alkyl-fulleropyrrolidines: Metal-Free-Mediated Reaction of [60]Fullerene with Aromatic Aldehydes and Inactive Primary Amines
Khalid A. Alamry, Li Liu, Hui-Juan Wang, Yong-Shun Huang, Fa-Bao Li, Chao-Yang Liu, Xin-Xin Zhong, Abdullah M. Asiri, Meng Zhang
The metal-free-mediated thermal reaction of [60]fullerene with aromatic aldehydes and inactive primary amines bearing electron-donating groups at the α-position afforded a series of 2-aryl-5-alkyl-fulleropyrrolidines, including the scarce 2-aryl-5-benzyl-fulleropyrrolidines as a mixture of cis and trans isomers. With rare exceptions, the mixture of cis and trans isomers could be easily isolated by column chromatography, with a preference of cis isomers as major products. A plausible mechanism for the formation of fulleropyrrolidines is also proposed.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01507

DOI: 10.1021/acs.joc.7b01507

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