Reactions of 2,2-dihydropolyfluoroalkylaldehydes with amines: a facile synthetic method for fluoroalkyl enaminoketones |
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Authors: | Xian-Jin Yang Fu-Lu Zhao |
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Institution: | Lab. of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China |
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Abstract: | Reactions of 2,2-dihydropolyfluoroalkylaldehydes (1) with amines (2) were studied. Both aliphatic amines and electron-deficient aromatic amines readily reacted with 1 in acetonitrile and water under reflux to give fluoroalkyl enaminoketones (3) in high yields, while no condensed products were obtained by reactions of 1 with electron-rich aromatic amines under similar conditions. In the presence of triethylamine, however, the reaction of 1 with electron-rich aromatic amines at room temperature gave 3 in low yields. |
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Keywords: | Fluoroalkylaldehydes Amines Nucleophilic addition Elimination Hydrolysis Fluoroalkyl enaminoketones Steric effect Electronic effect |
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