Novel β-hydroxy-β-bis(trifluoromethyl) imines |
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Authors: | Jan Alexander Barten Enno Lork |
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Institution: | a Hansa Fine Chemicals GmbH, Leobener Strasse, D-28334 Bremen, Germany b Institut für Anorganische & Physikalische Chemie, Universität Bremen, Leobener Strasse, D-28334 Bremen, Germany |
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Abstract: | Selected imines reacted with hexafluoroacetone non-catalyzed at ambient temperature to give β-hydroxy-β-bis(trifluoromethyl) imines in good to excellent yields. For the imines of acetone, pentan-3-one, and of cyclohexanone a 1:2 reaction was observed giving iminodiols; for N,N′-bis(propylidene)ethylene diamine an iminotetrol was formed. The diol derivative of N-isopropyl-propylidene amine could be deprotonated and O-methylated furnishing the respective ethers. Hexafluoropropylidene amine reacted with N-isopropyl-propylidene amine, unlike hexafluoroacetone, in a 1:1 manner to form an amino-imino alcohol which in its turn is able to add hexafluoroacetone. The imines of acetophenone, trifluoroacetone, 2,4-dimethyl-pentan-3-one, 2,6-dimethyl-cyclohexanone and of acetaldehyde added hexafluoroacetone to furnish β-iminoalcohols. A multifunctional β-hydroxy enaminone was obtained from 4-isopropylamino-pent-3-en-2-one. The molecular structures of the novel β-hydroxy-β-bis(trifluoromethyl) imines exhibit strong (R)N?HO hydrogen bonds. |
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Keywords: | β-Hydroxy-β-bis(trifluoromethyl) imines Hexafluoroacetone Ketimines Aldimine |
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