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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 1: 242 - 250

DOI: https://doi.org/10.6023/cjoc202307003

ARTICLES

N,N-Dimethylformamide-Promoted Synthesis of Fullerene-Fused Oxazoline Derivatives

  • Lijun Xu ,
  • Zongjun Li ,
  • Fushe Han ,
  • Xiang Gao
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  • a Green Chemistry and Process Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022
    b School of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei 230026
    c School of Material Science and Technology, Jilin Institute of Chemical Technology, Jilin 132022
*E-mail: ;
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Received date: 2023-07-08

  Revised date: 2023-08-27

  Online published: 2023-09-08

Supported by

Education Department Project of Jilin Province(JJKH20230287KJ)

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Abstract

Fullerene-fused oxazoline derivatives have been synthesized by many methods, however, the range of substrates is mainly limited to the aromatic substrates. Herein, a method for the synthesis of fullerene-fused oxazoline derivatives has been developed through the N,N-dimethylformamide (DMF)-promoted reaction of C60 with amides under basic conditions. The method was viable for both aliphatic and aromatic amides, providing the corresponding products in 27%~62% yields. It was found that DMF as a cosolvent could significantly improve the yield of the products. Mechanistic studies indicate that dianionic [60]fullero-oxazoline is key intermediate, and DMF plays a role in stabilizing dianion as demonstrated by in situ visible near infrared spectroscopy and control experiments. The electrochemical property study showed that, to compare with C60, fullerene-fused oxazoline derivatives of unsubstituted or substituted with an aryl group on oxazoline ring displayed only a slightly changed onset reduction potential, however, that for the derivatives decorated by an alkyl group such as Et on the oxazoline ring was apparently negatively shifted of up to 0.1 V.

Key words： fullerene-fused oxazoline derivatives; nucleophilic reaction; N,N-dimethylformamide; in situ visible near infrared spectroscopy; electrochemical property

Cite this article

Lijun Xu , Zongjun Li , Fushe Han , Xiang Gao . N,N-Dimethylformamide-Promoted Synthesis of Fullerene-Fused Oxazoline Derivatives[J]. Chinese Journal of Organic Chemistry, 2024 , 44(1) : 242 -250 . DOI: 10.6023/cjoc202307003

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