Wu Sheng-Li, Li Zong-Jun, Gao Xiang
State Key Laboratory of Electroanalytical Chemistry , Changchun Institute of Applied Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 5625 Renmin Street , Changchun , Jilin 130022 , China.
J Org Chem. 2019 Mar 15;84(6):3045-3054. doi: 10.1021/acs.joc.8b02462. Epub 2019 Mar 6.
Aerobic oxidation reaction of [70]fullerene with aliphatic primary thiols in the presence of n-butylamine was studied. The reaction afforded both the fullerene dithiol (2) and dithiol epoxide (3) compounds, which were characterized by H and C NMR, HRMS and UV-vis spectroscopies. In situ vis-NIR spectral measurement showed absorption bands due to anionic fullerene species, indicating that the reaction was likely initiated with the addition of thiolate anions to C. Computational calculations were performed to rationalize the structure of the dithiol epoxide compounds. The electrochemical property of 2,5-( n-CHS)C (2a) was compared with two analogue compounds of 2,5-BnC and 2-MeO-5-BnC that had identical addition pattern and number of addends. The result showed that the dithiol compound was more electron deficient than the other two derivatives.
研究了在正丁胺存在下，[70]富勒烯与脂肪族伯硫醇的有氧氧化反应。该反应得到了富勒烯二硫醇（2）和二硫醇环氧化物（3）化合物，通过氢谱、碳谱、高分辨质谱和紫外可见光谱对其进行了表征。原位可见近红外光谱测量显示了由于阴离子富勒烯物种产生的吸收带，表明该反应可能是由硫醇阴离子加成到C上引发的。进行了计算计算以合理化二硫醇环氧化合物的结构。将2,5-(n-CHS)C（2a）的电化学性质与具有相同加成模式和加成数的2,5-BnC和2-MeO-5-BnC的两种类似化合物进行了比较。结果表明，二硫醇化合物比其他两种衍生物的电子缺乏程度更高。
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