"Click" and Olefin Metathesis Chemistry in Water at Room Temperature Enabled by Biodegradable Micelles.
"Click" and Olefin Metathesis Chemistry in Water at Room Temperature Enabled by Biodegradable Micelles.
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室温下水中的“点击”和烯烃复分解化学由可生物降解的胶束实现。
DOI：
10.1021/ed300893u
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发表时间：
2013
影响因子：
3
通讯作者：
Wenzel,AnnaG
中科院分区：
文献类型：
--
作者：
Lipshutz,BruceH;Boskovic,Zarko;Crowe,ChristopherS;Davis,VictoriaK;Whittemore,HannahC;Vosburg,DavidA;Wenzel,AnnaG
这两个实验室反应的重点是教授与绿色化学相关的几个概念。每一种都使用一种商业的、无毒的、可生物降解的表面活性剂TPGS-750-M，以促进水中纳米级胶束的亲脂核心内的有机反应。这些实验是基于K.巴里·夏普莱斯和罗伯特·格拉布斯的工作；这两个实验都适合本科生有机实验室。铜催化叠氮化苄和4-甲苯基乙炔的[3+2]环加成反应非常迅速：三唑产物很容易通过过滤分离，并用薄层色谱和熔点分析进行了表征。用薄层层析法和气相色谱法可以很好地监测Ru催化的丙烯酸苄酯和1-己烯的烯烃交叉歧化反应。复分解实验比较了TPGS-750-M/水介质与在二氯甲烷(一种常见的烯烃复分解溶剂)中进行的传统反应的有效性。
The two laboratory reactions focus on teaching several concepts associated with green chemistry. Each uses a commercial, nontoxic, and biodegradable surfactant, TPGS-750-M, to promote organic reactions within the lipophilic cores of nanoscale micelles in water. These experiments are based on work by K. Barry Sharpless (an azide–alkyne “click” reaction) and Robert Grubbs (an olefin cross-metathesis reaction); both are suitable for an undergraduate organic laboratory. The copper-catalyzed azide–alkyne [3 + 2] cycloaddition of benzyl azide and 4-tolylacetylene is very rapid: the triazole product is readily isolated by filtration and is characterized by thin-layer chromatography and melting point analysis. The ruthenium-catalyzed olefin cross-metathesis reaction of benzyl acrylate with 1-hexene is readily monitored by thin-layer chromatography and gas chromatography. The metathesis experiment comparatively evaluates the efficacy of a TPGS-750-M/water medium relative to a traditional reaction performed in dichloromethane (a common solvent used for olefin metathesis).