【摘要】：羧酸酯是一類重要的化工原料,可作為香料、溶劑、增塑劑及有機(jī)合成中間體廣泛使用;同時在高分子聚合物、藥物、液晶材料等研究領(lǐng)域也具有重要的應(yīng)用價值。因此,發(fā)展更溫和、高效、經(jīng)濟(jì)、綠色的合成羧酸酯的方法依然是有機(jī)化學(xué)合成領(lǐng)域的一個有挑戰(zhàn)性的課題。近年來,化學(xué)家們成功的發(fā)現(xiàn)一些含硫試劑的C-S鍵活化斷裂脫硫作為烷基化試劑參與反應(yīng)。常用的含硫試劑有如磺酰肼、磺酰胺、磺酰氯、亞磺酸鹽、硫醚、硫醇(酚)、Buntes鹽等。從經(jīng)濟(jì)角度考慮,首選廉價、易得的試劑。而Buntes鹽作為�；噭┑膽�(yīng)用還未見文獻(xiàn)報道。本論文首先對Buntes鹽和二硫醚作為硫源在催化偶聯(lián)中的應(yīng)用作了簡單的綜述,接著有對酯合成方法作了簡單的綜述,最后根據(jù)大量實驗數(shù)據(jù),得到一個新的、經(jīng)濟(jì)的酯合成新方法。該反應(yīng)以溴化亞銅作為氧化劑,咪唑為配體,碳酸鈉為堿,Buntes鹽與苯酚衍生物為底物,在100 oC條件下直接生成一系列的苯甲酸苯酯衍生物。實驗結(jié)果表明該反應(yīng)對具有吸電子的Buntes和帶有給電子的酚類衍生物具有很好的兼容性。所得的化合物均通過1H NMR,13C NMR鑒定確定結(jié)構(gòu)。通過一定的文獻(xiàn)參考以及一些控制實驗研究推斷出可能的反應(yīng)機(jī)理。
[Abstract]:Carboxylate is an important kind of chemical raw materials, which can be widely used as spices, solvents, plasticizers and organic synthesis intermediates, and also has important application value in polymer, medicine, liquid crystal materials and other research fields. Therefore, the development of more moderate, efficient, economical and green methods for the synthesis of carboxylate is still a challenging topic in the field of organic chemistry synthesis. In recent years, chemists have successfully found that some sulfur-containing reagents are activated by C-S bonds and broken desulfurization as alkylation reagents to participate in the reaction. Commonly used sulfur-containing reagents such as sulfonyl hydrazine, sulfonamide, sulfonyl chloride, sulfonate, sulfide, mercaptan (phenolic), Buntes salt, etc. From an economic point of view, the first choice of cheap, easily available reagent. However, the application of Buntes salt as acylation reagent has not been reported. In this paper, the application of Buntes salt and disulfide as sulfur source in catalytic coupling was briefly reviewed, and then the synthesis method of ester was briefly reviewed. Finally, according to a large number of experimental data, a new method was obtained. A new economic method for synthesis of esters. In this reaction, a series of benzyl benzoate derivatives were synthesized directly under the condition of 100 oC with copper bromide as oxidant, imidazole as ligand, sodium carbonate as base, Buntes salt and phenol derivative as substrate. The experimental results show that the reaction has good compatibility with Buntes with electron absorption and phenolic derivatives with electron donating. The compounds were identified by 1H NMR,13C NMR. The possible reaction mechanism was inferred by some references and some control experiments.
【學(xué)位授予單位】：鄭州大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O621.25

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本文編號：2262440