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

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

研究论文

N,N-二甲基甲酰胺促进的富勒烯稠合噁唑啉衍生物的合成

  • 徐利军 ,
  • 李宗军 ,
  • 韩福社 ,
  • 高翔
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  • a 中国科学院长春应用化学研究所 绿色化学与过程实验室 长春 130022
    b 中国科学技术大学应用化学与工程学院 合肥 230026
    c 吉林化工学院材料科学与工程学院 吉林 132022

收稿日期: 2023-07-08

  修回日期: 2023-08-27

  网络出版日期: 2023-09-08

基金资助

吉林省教育厅(JJKH20230287KJ)

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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: ;
E-mail:

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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摘要

富勒烯稠合噁唑啉衍生物的合成已建立多种方法, 但绝大多数方法仅限于芳香族类底物. 发展了一种N,N-二甲基甲酰胺(DMF)促进富勒烯C60与酰胺类底物在碱性条件下合成富勒烯稠合噁唑啉的方法, 该方法对脂肪族和芳香族酰胺均具有较好的兼容性, 能以27%~62%的收率成功合成了一系列富勒烯稠合噁唑啉衍生物. 实验结果表明N,N-二甲基甲酰胺(DMF)在此反应中作为共溶剂, 可以显著提高目标化合物的收率. 现场可见近红外吸收光谱和对照实验研究表明, 富勒烯稠合噁唑啉二负离子是反应的关键中间体, DMF有利于此二负离子的生成并对此二负离子起到稳定作用. 电化学性质研究显示, 富勒烯稠合噁唑啉产物的噁唑啉环上不含取代基和含芳基取代基的衍生物, 其起始还原电位相对于C60无明显变化, 但噁唑啉环上含脂肪烷基的衍生物的起始还原电位有较大负移, 达到0.1 V.

关键词： 富勒烯稠合噁唑啉衍生物; 亲核反应; N,N-二甲基甲酰胺; 现场可见近红外吸收光谱; 电化学性质

本文引用格式

徐利军 , 李宗军 , 韩福社 , 高翔 . N,N-二甲基甲酰胺促进的富勒烯稠合噁唑啉衍生物的合成[J]. 有机化学, 2024 , 44(1) : 242 -250 . DOI: 10.6023/cjoc202307003

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

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