微波辅助迈克尔加成反应和乌尔曼反应的研究
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摘要
迈克尔加成反应和乌尔曼反应是两类重要的反应。一直是有机化学领域的研究热点。为研究微波下迈克尔反应的规律,本文采用单模聚焦微波有机合成仪,通过对顺丁烯二酸、反丁烯二酸和氨水合成DL-天冬氨酸、顺式3-甲基丁烯二酸和氨水合成3-甲基天冬氨酸、丙烯酸甲酯和氨水合成β-丙氨酸、丙烯腈和氨水合成β-氨基丙腈等五个反应对迈克尔加成反应进行了研究。并通过正交实验优化,得出合成DL-天冬氨酸、β-丙氨酸、β-氨基丙腈的较佳工艺条件;通过单因素实验,考察了微波功率、微波时间、反应温度、溶剂等因素对迈克尔加成反应的影响。实验表明,在微波辐射条件下,顺式比反式迈克尔反应活性高;若在丁烯二酸的双键上引入甲基后,降低了进行迈克尔加成反应的活性;引入酯基对双键的影响比腈基有利于进行迈克尔反应,丙烯酸甲酯较丙烯腈的迈克尔反应活性高。
三苯胺及其衍生物是制备电荷传输材料,电致发光材料等的重要原材料,同时也可以作为有机染料和医药中间体。本文在微波下采用溴苯或氯苯代替传统方法中的碘苯,通过二苯胺与溴苯、氯苯合成三苯胺、4,4'-二甲基二苯胺和溴苯合成4,4'-二甲基三苯胺以及对硝基苯胺和4-氯硝基苯合成4,4',4''-三硝基三苯胺等反应研究微波对乌尔曼反应的影响,并通过正交实验优化,得出了合成三苯胺、4,4'-二甲基三苯胺、4,4',4''-三硝基三苯胺较佳工艺条件;通过单因素试验,考察了微波时间、微波功率、反应温度、溶剂等因素对乌尔曼反应的影响。实验结果表明,微波条件下,当三苯胺衍生物的苯环上连有供电子基团时,它比三苯胺难合成;当它的苯环上连有吸电子基团时,它比三苯胺易合成;不同卤代苯进行乌尔曼反应时,原子半径大的卤素更能促进反应进行。
总之,微波加热下,迈克尔加成反应和乌尔曼反应活性的影响规律与常规加热一致,微波加热,与传统加热相比,对迈克尔加成反应和乌尔曼反应都具有快速、节能环保、操作简单、经济、安全等优点。
Michael Reaction and Ullmann Reaction are two types of important reactions which are always the focus in organic chemistry. In order to study the influence of microwave radiation on Michael reaction, single module focusing microwave reactor was employed for five Michael addition reactions, including: DL-aspartic acid formed by treating the maleic acid or fumaric acid with ammonia; 3-methyl maleic acid formed by treating the 3-methyl maleic acid with ammonia; beta-alanin formed by treating methyl acrylate with ammonia; beta-aminopropionitrile formed by treating acrylonitrile with ammonia in this paper. The better technology parameters of synthesis of DL-aspartic acid, beta-alanin and beta-aminopropionitrile were obtained through the orthogonal test. Effects of microwave power, reaction time, reaction temperature, solvent etc. on reaction were studied by a single factor tests. The results show that maleic acid is more active than fumaric acid; the introduction of methyl group on the double bond can weak the reactivity of the Michael addition reaction; the ester base is more propitious to complete the Michael addition reaction than the nitrile base.
Triphenylamine and its derivatives are important raw materials which can be produced charge transport material and electro-luminescent materials. They are also used as organic dyestuffs and the pharmaceutical intermediate materials. The influence of microwave radiation on Ullmann reaction has been investigated by three Ullmann reactions, including triphenylamine formed by treating the diphenylamine with bromobenzene or Chlorobenzene which substitutes Iodobenzene; 4,4'-dimethyltriphenylamine formed by treating 4,4'-dimethyldiphenylamine with bromobenzene which substitutes Iodobenzene; 4,4',4"-trinitrotriphenylamine formed by treating 4-chloronitrobenzene with p-nitroaniline in this paper. The better technology parameters of synthesis of triphenylamine, 4,4'-dimethyltriphenylamine and 4,4',4"-trinitrotriphenylamine were obtained through the orthogonal test. Effects of microwave power, reaction time, reaction temperature, solvent, etc. on reaction were studied by a single factor test. The results showed that the derivatives of triphenylamine which their phenyl were connected the donor substituent were harder to be synthesized than the triphenylamine; the derivatives of triphenylamine which their phenyl were connected the acceptor substituents were easier to be synthesized than the triphenylamine; the Ullmann reaction was easy to process when the halogenated benzene which their halogen’radius was bigger under microwave irradiation.
In a word, law of Michael reaction and Ullmann Reactions under microwave radiation is the same as that on conventional heating conditions. Microwave heating is much faster, energy-saving and environmental, simpler operation, more economical and safer than conventional heating for Ullmann Reactions and Ullmann Reactions.
三苯胺及其衍生物是制备电荷传输材料,电致发光材料等的重要原材料,同时也可以作为有机染料和医药中间体。本文在微波下采用溴苯或氯苯代替传统方法中的碘苯,通过二苯胺与溴苯、氯苯合成三苯胺、4,4'-二甲基二苯胺和溴苯合成4,4'-二甲基三苯胺以及对硝基苯胺和4-氯硝基苯合成4,4',4''-三硝基三苯胺等反应研究微波对乌尔曼反应的影响,并通过正交实验优化,得出了合成三苯胺、4,4'-二甲基三苯胺、4,4',4''-三硝基三苯胺较佳工艺条件;通过单因素试验,考察了微波时间、微波功率、反应温度、溶剂等因素对乌尔曼反应的影响。实验结果表明,微波条件下,当三苯胺衍生物的苯环上连有供电子基团时,它比三苯胺难合成;当它的苯环上连有吸电子基团时,它比三苯胺易合成;不同卤代苯进行乌尔曼反应时,原子半径大的卤素更能促进反应进行。
总之,微波加热下,迈克尔加成反应和乌尔曼反应活性的影响规律与常规加热一致,微波加热,与传统加热相比,对迈克尔加成反应和乌尔曼反应都具有快速、节能环保、操作简单、经济、安全等优点。
Michael Reaction and Ullmann Reaction are two types of important reactions which are always the focus in organic chemistry. In order to study the influence of microwave radiation on Michael reaction, single module focusing microwave reactor was employed for five Michael addition reactions, including: DL-aspartic acid formed by treating the maleic acid or fumaric acid with ammonia; 3-methyl maleic acid formed by treating the 3-methyl maleic acid with ammonia; beta-alanin formed by treating methyl acrylate with ammonia; beta-aminopropionitrile formed by treating acrylonitrile with ammonia in this paper. The better technology parameters of synthesis of DL-aspartic acid, beta-alanin and beta-aminopropionitrile were obtained through the orthogonal test. Effects of microwave power, reaction time, reaction temperature, solvent etc. on reaction were studied by a single factor tests. The results show that maleic acid is more active than fumaric acid; the introduction of methyl group on the double bond can weak the reactivity of the Michael addition reaction; the ester base is more propitious to complete the Michael addition reaction than the nitrile base.
Triphenylamine and its derivatives are important raw materials which can be produced charge transport material and electro-luminescent materials. They are also used as organic dyestuffs and the pharmaceutical intermediate materials. The influence of microwave radiation on Ullmann reaction has been investigated by three Ullmann reactions, including triphenylamine formed by treating the diphenylamine with bromobenzene or Chlorobenzene which substitutes Iodobenzene; 4,4'-dimethyltriphenylamine formed by treating 4,4'-dimethyldiphenylamine with bromobenzene which substitutes Iodobenzene; 4,4',4"-trinitrotriphenylamine formed by treating 4-chloronitrobenzene with p-nitroaniline in this paper. The better technology parameters of synthesis of triphenylamine, 4,4'-dimethyltriphenylamine and 4,4',4"-trinitrotriphenylamine were obtained through the orthogonal test. Effects of microwave power, reaction time, reaction temperature, solvent, etc. on reaction were studied by a single factor test. The results showed that the derivatives of triphenylamine which their phenyl were connected the donor substituent were harder to be synthesized than the triphenylamine; the derivatives of triphenylamine which their phenyl were connected the acceptor substituents were easier to be synthesized than the triphenylamine; the Ullmann reaction was easy to process when the halogenated benzene which their halogen’radius was bigger under microwave irradiation.
In a word, law of Michael reaction and Ullmann Reactions under microwave radiation is the same as that on conventional heating conditions. Microwave heating is much faster, energy-saving and environmental, simpler operation, more economical and safer than conventional heating for Ullmann Reactions and Ullmann Reactions.
引文
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