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Efficient Synthesis of β-Chlorovinylketones from Acetylene in Chloroaluminate Ionic Liquids

Dennis J. M. Snelders and Paul J. Dyson

*Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland, Email: paul.dysonepfl.ch

D. J. M. Snelders, P. J. Dyson, Org. Lett., 2011, 13, 4048-4051.

DOI: 10.1021/ol201182t (free Supporting Information)


Abstract

In a method for the Friedel-Crafts-type insertion reaction of acetylene with acid chlorides in chloroaluminate ionic liquids, the use of ionic liquids not only serves to avoid the use of carbon tetrachloride or 1,2-dichloroethane but also suppresses side reactions, and enables a simpler purification procedure, giving a range of aromatic and aliphatic β-chlorovinyl ketones in high yield and purity.

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Key Words

Friedel-Crafts Acylation, enones, vinyl chlorides, green chemistry, ionic liquids


ID: J54-Y2011-2190