Ionic liquids a new reaction media in ETC: reactivity and selectivity studies

ORGN 420

Mickael Pauvert, William Pomerantz, and Olaf Wiest. Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556
Ionic liquids are new and interesting media for a wide variety of reactions. Salts that are liquid at room temperature or below were known for some time, but their unusual physical properties and potential as replacement for a variety of organic solvents as reaction media triggered intense research over the last few years. Their unique properties make them particularly promising as solvents for ETC (electron transfer catalysis) reactions since they facilitate the electron transfer, increase the lifetime of the radical cation intermediates and simplify the isolation of the products. The dimerization of electron rich styrenes such as vinyl anisole is a suitable test system because they lead to interesting lignane and neolignane products and the competition between (2+2) and (4+2) ETC cycloaddition is well understood. We report our investigation about differences in reaction rates, regioselectivity and stereoselectivity between ionic liquids and conventional organic solvents.