Reactions of β-alkoxyvinyl polyfluoroalkyl ketones with ethyl isocyanoacetate and its use for the synthesis of new polyfluoroalkyl pyrroles and pyrrolidines

…, II Gerus, K Bergander, R Fröhlich, G Haufe

Index: Kondratov, Ivan S.; Dolovanyuk, Violetta G.; Tolmachova, Nataliya A.; Gerus, Igor I.; Bergander, Klaus; Froehlich, Roland; Haufe, Guenter Organic and Biomolecular Chemistry, 2012 , vol. 10, # 44 p. 8778 - 8785

Full Text: HTML

Citation Number: 15

Abstract

The hitherto unreported reactions of β-alkoxyvinyl polyfluoroalkyl ketones with ethyl isocyanoacetate and equimolar amounts of potassium-tert-butoxide proceeded mainly in the β-position of the α, β-unsaturated ketones in cases of α-nonsubstituted 1a–e and α-methyl substituted ketones 1g–j. Other α-or β-substituted ketones 1f, k–o gave mainly products 4 of initial attack at the carbonyl carbon. Depending on the solvent, the major products of β- ...