有机高价碘试剂在不饱和羧酸的溴代内酯化反应中的应用研究
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摘要
第一章综述。首先详细地介绍了有机高价碘试剂的典型代表二醋酸碘苯在有机合成中的新的应用成果。随着科研工作者的不断深入研究,二醋酸碘苯被广泛运用于各种有机反应中,取得了很好的效果。
第二章不饱和羧酸的溴代内酯化反应的研究。卤代内酯化反应是一个重要的有机反应,它的反应产物卤代内酯作为反应中间体在有机合成中有着广泛的应用。溴代内酯的合成方法主要是不饱和羧酸与溴的反应,由于溴单质是一种有毒的易挥发腐蚀性液体,该性质影响了溴代内酯化反应的广泛应用,而寻找新的简单高效的溴代内酯化方法是我们研究的主要内容。有机高价碘试剂是温和的氧化剂,与重金属Hg(Ⅱ), Tl(Ⅲ)和Pb(Ⅳ)等化合物具有相似的化学反应特性,但无毒,不会对环境造成污染等特点,符合目前大力提倡的绿色化学的发展要求。使用有机高价碘试剂,我们考察了新的溴代内酯化反应,取得了良好的结果。
本章共分三部分,首先介绍了不饱和羧酸与溴化物在二醋酸碘苯作用下发生的溴代内酯化反应。通过大量的实验,我们发现在常温条件下甲醇溶剂中,不饱和羧酸和过量的溴化锂及等当量的二醋酸碘苯很容易反应,短时间内就能获得良好产率的溴代内酯化产物,其中最高产率可达到95%。第二部分研究了在催化量的有机高价碘试剂作用下的不饱和羧酸的溴代内酯化反应,取得了理想的结果:在常温条件下CF3CH2OH溶剂中,用二醋酸碘苯作催化剂,以Oxone○R(KHSO4·2KHSO5·K2SO4)为氧化剂,考察了不饱和羧酸与溴化钠的溴代内酯化反应,得到了良好产率的溴代内酯化产物。该两种不饱和羧酸在二醋酸碘苯作用下的溴代内酯化反应具有反应条件温和,简单高效,绿色环保等优点。研究成果扩大了有机高价碘试剂在有机合成中的应用范围。第三部分介绍了我们最近的发现成果:用碘化钾或碘分子代替二醋酸碘苯在温和的反应条件下也能得到较高产率的溴代内酯化产物,反应可能经过一个有机高价碘中间体,有关研究正在进行中。
In chapter one, the new application of (diacetoxyiodo)benzene(DIB) as a typical representative of hypervalent iodion regents in organic synthesis has been reviewed in detail. DIB has been widely applied in organic reactions, and obtaining many good results.
In chapter two, the bromolactonization of alkenoic acids has been discussed. Lactonizations have been studied extensively, and this type of transformation serves as an important key reaction in a variety of syntheses. Usually, alkenoic acids are used to construct bromolactones with molecular bromine. However, bromolactonization has the restriction of molecular bromine is a toxic, difficult to handle, low-boiling lachrymatory liquid. Organic hypervalent iodine reagents have been received much attention due to their low toxicity, mild reactivity, ready availability, high stability and easy handing. They have found broad application in organic chemistry as alternatives replacing the highly toxic Hg(II), Tl(III) and Pb(IV) heavy-metal oxidants. Using hypervalent iodine reagents, the cyclization of alkenoic acids was investigated and found that the reaction was suitable for a series of 4-pentenoic acids, most of which gave good to excellent yields.
In the first part of chapter two, it was found that the reaction of alkenoic acids with one equivalent of DIB and two equivalents of lithium bromide was easily be carried out in methanol at room temperature, got the bromolactones in good yields, in which the biggest yield can reach 95%. Then, the bromolactonization of alkenoic acids under catalytic hypervalent iodion regent was investigated. It was found when DIB was used as catalyst and Oxone○R ( KHSO4·2KHSO5·K2SO4)was used as co-oxidant, the reaction of alkenoic acids with sodium bromide was also fluent in CF3CH2OH at room temperature, obtaining good yields of bromolactones. In the last part, the new improvement for the bromolactonization of alkenoic acids is reported: the bromolactonization of alkenoic acid using catalytic KI or I2 to replace catalytic hypervalent iodion regent is also effect, giving good yield of bromolactone.
In conclusion, the methods for bromolactonization of alkenoic acids have the advantages such as mild reaction conditions, simple procedure and“green”. Furthermore, the scope of use of hypervalent iodine reagents in organic synthesis have be extended.
第二章不饱和羧酸的溴代内酯化反应的研究。卤代内酯化反应是一个重要的有机反应,它的反应产物卤代内酯作为反应中间体在有机合成中有着广泛的应用。溴代内酯的合成方法主要是不饱和羧酸与溴的反应,由于溴单质是一种有毒的易挥发腐蚀性液体,该性质影响了溴代内酯化反应的广泛应用,而寻找新的简单高效的溴代内酯化方法是我们研究的主要内容。有机高价碘试剂是温和的氧化剂,与重金属Hg(Ⅱ), Tl(Ⅲ)和Pb(Ⅳ)等化合物具有相似的化学反应特性,但无毒,不会对环境造成污染等特点,符合目前大力提倡的绿色化学的发展要求。使用有机高价碘试剂,我们考察了新的溴代内酯化反应,取得了良好的结果。
本章共分三部分,首先介绍了不饱和羧酸与溴化物在二醋酸碘苯作用下发生的溴代内酯化反应。通过大量的实验,我们发现在常温条件下甲醇溶剂中,不饱和羧酸和过量的溴化锂及等当量的二醋酸碘苯很容易反应,短时间内就能获得良好产率的溴代内酯化产物,其中最高产率可达到95%。第二部分研究了在催化量的有机高价碘试剂作用下的不饱和羧酸的溴代内酯化反应,取得了理想的结果:在常温条件下CF3CH2OH溶剂中,用二醋酸碘苯作催化剂,以Oxone○R(KHSO4·2KHSO5·K2SO4)为氧化剂,考察了不饱和羧酸与溴化钠的溴代内酯化反应,得到了良好产率的溴代内酯化产物。该两种不饱和羧酸在二醋酸碘苯作用下的溴代内酯化反应具有反应条件温和,简单高效,绿色环保等优点。研究成果扩大了有机高价碘试剂在有机合成中的应用范围。第三部分介绍了我们最近的发现成果:用碘化钾或碘分子代替二醋酸碘苯在温和的反应条件下也能得到较高产率的溴代内酯化产物,反应可能经过一个有机高价碘中间体,有关研究正在进行中。
In chapter one, the new application of (diacetoxyiodo)benzene(DIB) as a typical representative of hypervalent iodion regents in organic synthesis has been reviewed in detail. DIB has been widely applied in organic reactions, and obtaining many good results.
In chapter two, the bromolactonization of alkenoic acids has been discussed. Lactonizations have been studied extensively, and this type of transformation serves as an important key reaction in a variety of syntheses. Usually, alkenoic acids are used to construct bromolactones with molecular bromine. However, bromolactonization has the restriction of molecular bromine is a toxic, difficult to handle, low-boiling lachrymatory liquid. Organic hypervalent iodine reagents have been received much attention due to their low toxicity, mild reactivity, ready availability, high stability and easy handing. They have found broad application in organic chemistry as alternatives replacing the highly toxic Hg(II), Tl(III) and Pb(IV) heavy-metal oxidants. Using hypervalent iodine reagents, the cyclization of alkenoic acids was investigated and found that the reaction was suitable for a series of 4-pentenoic acids, most of which gave good to excellent yields.
In the first part of chapter two, it was found that the reaction of alkenoic acids with one equivalent of DIB and two equivalents of lithium bromide was easily be carried out in methanol at room temperature, got the bromolactones in good yields, in which the biggest yield can reach 95%. Then, the bromolactonization of alkenoic acids under catalytic hypervalent iodion regent was investigated. It was found when DIB was used as catalyst and Oxone○R ( KHSO4·2KHSO5·K2SO4)was used as co-oxidant, the reaction of alkenoic acids with sodium bromide was also fluent in CF3CH2OH at room temperature, obtaining good yields of bromolactones. In the last part, the new improvement for the bromolactonization of alkenoic acids is reported: the bromolactonization of alkenoic acid using catalytic KI or I2 to replace catalytic hypervalent iodion regent is also effect, giving good yield of bromolactone.
In conclusion, the methods for bromolactonization of alkenoic acids have the advantages such as mild reaction conditions, simple procedure and“green”. Furthermore, the scope of use of hypervalent iodine reagents in organic synthesis have be extended.
引文
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