正丁胺通过有氧氧化反应引发[60]富勒烯与脂肪族伯硫醇的二硫化反应

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2024-10-22 DOI:10.1016/j.tet.2024.134313

Sheng-Li Wu , Yu-Bo Li , Song-Xiao Yu , Peiwen Lv , Jintao Guan , Yi Wang , Zong-Jun Li

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引用次数: 0

摘要

研究了由正丁胺引发的[60]富勒烯与脂肪族伯硫醇的简易有氧氧化反应。有趣的是，该反应在溶剂蒸发后会产生液态混合物，而不是典型的固态混合物。通过 HPLC 对反应产物进行纯化，分离出富勒烯二硫环氧化物化合物 (2)，并通过 1H NMR、13C NMR、HRMS 和 UV-Vis 光谱对其进行了广泛表征。研究人员提出了形成所观察到的产物的合理反应机制。为阐明所提出的反应机制，进行了计算模拟和对照实验。研究了 1,2-O-4,15-(n-C5H11S)2C60 (2) 的电化学行为，揭示了其在逐渐还原时的不稳定性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Dithiolation of [60]fullerene with aliphatic primary thiols initiated by n-butylamine via aerobic oxidation reaction

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Dithiolation of [60]fullerene with aliphatic primary thiols initiated by n-butylamine via aerobic oxidation reaction

A facile aerobic oxidation reaction of [60]fullerene with aliphatic primary thiols initiated by n-butylamine was studied. Interestingly, the reaction yielded liquid mixtures upon solvent evaporation, contrary to the typical formation of solid mixtures. The reaction products were purified using HPLC to isolate the fullerene dithiol epoxide compound (2), which was extensively characterized by ¹H NMR, ¹³C NMR, HRMS, and UV–Vis spectra. Plausible reaction mechanisms leading to the formation of the observed products were proposed. Computational simulations and control experiment were conducted to elucidate the proposed reaction mechanisms. The electrochemical behavior of 1,2-O-4,15-(n-C₅H₁₁S)₂C₆₀ (2) was investigated, revealing its instability upon gradual reduction.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.