摘要碳碳双键广泛存在于天然产物及药物分子中，且其在有机合成中担当着很重要的角色，因而人们一直在探索高效构建碳碳双键的方法。最经典的便是Wittig反应，后来人们发现重氮化合物也可以与醛在金属配合物的催化下发生Wittig反应，这类反应在近十年来比较热门。然而，重氮化物若邻位没有吸电基，则很不稳定，具有易爆炸及致癌的性质，因此应用受到很大的限制。N-对甲苯磺酰腙在碱的存在下，可以原位生成重氮化物，从而为无吸电基稳定的重氮化合物的应用提供了一个新的路径。本文就以N-对甲苯磺酰腙为起始物，对Wittig反应进行了系统的研究。通过实验发现廉价的Cu催化剂可以代替昂贵的金属催化剂来催化Wittig反应，得到选择性很好的反式烯烃，其中Cu(acac)2有很高的催化活性，有很好的应用前景。另外，在无金属条件下，磺酰腙也可以在碱的条件下与醛生成二亚烷基联肼，这类化合物通过其他方法较难合成，此方法能一步合成，因此也具有一定的应用前景。62954

毕业论文关键词 ： 碳碳双键  Wittig反应  重氮化合物  金属配合物  烯烃  合成

毕业设计说明书（论文）外文摘要

Title:  The Study of the Hydrazone Participation Synthesis Reaction

Abstract Carbon-carbon double bond is widespread in the natural products and drug molecules, and it plays a very important role in organic synthesis, so people have been exploring efficient ways to build a carbon-carbon double bond. The most classic is the Wittig reaction, and later it was discovered that the diazo compound can participate in Wittig reaction with aldehydes catalyzed by metal complexes, such reactions are more and more popular in the last decade. However, if diazide does not have electron withdrawing group at the ortho, it is very unstable, with explosive and carcinogenic nature, so the application is greatly limited. But in the presence of a base N-tosyl hydrazone can generate diazide in situ. Thus it provides a new application of no stable electron-withdrawing diazonium compound. Using N-tosyl hydrazone as starting materials this article carried out a systematic study of the Wittig reaction. Found by experiments cheap Cu catalyst can catalytic Wittig reaction instead of expensive metal catalyst, and can get good selective trans olefin, Cu (acac) 2 has a high catalytic activity, and it is a good prospect of application. Further, in the metal-free conditions, sulfonyl hydrazone can generate the dialkylene associated hydrazine with an aldehyde under the conditions of alkali, such compounds are difficult to synthesize by other methods, but this method can synthesis them though one step, and therefore has certain application prospects.

Keywords：Carbon-carbon Double Bond，Wittig Reaction ，Diazo Compound， Metal Complexes，Olefin，Synthesis

1  绪论 1

1.1 Wittig反应简介 1

1.2 Wittig反应的早期研究 1

1.3 Wittig反应的改进 2

1.3.1 Wittig-Horner反应[7-9] 2

1.3.2 Schlosser改进 2

1.3.3 Horner-Wadsworth-Emmons反应 2

1.4腙参与的Wittig反应研究 2

1.4.1条件优化 3

1.4.2金属催化下腙参与的Wittig反应探究 3

1.4.3 无金属条件下腙参与的Wittig反应探究 4

1.5 本论文的研究内容及意义 4

1.5.1 本论文的研究内容