Lipshutz Bruce H, Bošković Zarko, Crowe Christopher S, Davis Victoria K, Whittemore Hannah C, Vosburg David A, Wenzel Anna G
Department of Chemistry & Biochemistry, University of California, Santa Barbara, 93106, United States.
J Chem Educ. 2013 Nov 12;90(11). doi: 10.1021/ed300893u.
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).
这两个实验室反应着重于教授与绿色化学相关的几个概念。每个反应都使用一种商业的、无毒且可生物降解的表面活性剂TPGS - 750 - M，以促进水中纳米级胶束亲脂性核心内的有机反应。这些实验基于K. Barry Sharpless的工作（叠氮化物 - 炔烃“点击”反应）和Robert Grubbs的工作（烯烃交叉复分解反应）；两者都适用于本科有机化学实验室。铜催化的苄基叠氮化物与4 - 甲苯乙炔的叠氮化物 - 炔烃[3 + 2]环加成反应非常迅速：三唑产物很容易通过过滤分离出来，并通过薄层色谱和熔点分析进行表征。钌催化的丙烯酸苄酯与1 - 己烯的烯烃交叉复分解反应很容易通过薄层色谱和气相色谱进行监测。复分解实验比较评估了TPGS - 750 - M/水介质相对于在二氯甲烷（烯烃复分解常用的一种常见溶剂）中进行的传统反应的效果。
