“Click” and Olefin Metathesis Chemistry in Water at Room Temperature Enabled by Biodegradable Micelles
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).
© 2013, ACS Publications
“‘Click’ and olefin metathesis chemistry in water at room temperature enabled by biodegradable micelles,” Lipshutz, B.H.; Boskovic, Z.; Crowe, C.S.; Davis, V.K.; Whittemore, H.C.; Vosburg, D.A.; Wenzel, A.G. J. Chem. Educ. 2013, 90, 1514-1517.