Novel β-hydroxy-β-bis(trifluoromethyl) imines

Selected imines reacted with hexafluoroacetone non-catalyzed at ambient temperature to give beta-hydroxy-beta-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 beta-iminoalcohols. A multifunctional beta-hydroxy enaminone was obtained from 4-isopropylamino-pent-3-en-2-one. The molecular structures of the novel beta-hydroxy-beta-bis(trifluoromethyl) imines exhibit strong =(R)N...H-O- hydrogen bonds. (C) 2004 Elsevier B.V. All rights reserved.