title: "Click" and Olefin Metathesis Chemistry in Water at Room Temperature Enabled by Biodegradable Micelles.
abstract: 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).
authors: Department of Chemistry & Biochemistry, University of California, Santa Barbara, 93106, United States.
authors: Bruce H
authors: BH
authors: Lipshutz
authors: Zarko
authors: Z
authors: Bošković
authors: Christopher S
authors: CS
authors: Crowe
authors: Victoria K
authors: VK
authors: Davis
authors: Hannah C
authors: HC
authors: Whittemore
authors: David A
authors: DA
authors: Vosburg
authors: Anna G
authors: AG
authors: Wenzel
keywords: aqueous solution chemistry; catalysis; green chemistry; laboratory instruction; micelles; microscale lab; organic chemistry; second-year undergraduate; solutions/solvents; upper-division undergraduate