Easy Synthesis of New Chiral Tetradentate N4 Schiff Bases and Their Use as Ligands for Metal Complexes

The chiral N4 Schiff bases (1R,2R)‐N,N′‐bis(2‐p‐tosylaminobenzylidene)‐1,2‐diaminocyclohexane (H2CyTs, 1), (1R,2R)N,N′‐bis(2‐trifluoromethylsulfonaminobenzylidene)‐1,2‐diaminocyclohexane (H2CyTf, 2), (1R,2R)‐N,N′‐bis(2‐aminobenzylidene)‐1,2‐diaminocyclohexane (3) and (1R,2R)‐N,N′‐bis(2‐nitrobenzylid...

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Bibliographic Details
Published in:European journal of organic chemistry 2003-04, Vol.2003 (7), p.1271-1276
Main Authors: Karamé, Iyad, Tommasino, M. Lorraine, Faure, René, Lemaire, Marc
Format: Article
Language:English
Subjects:
Cobalt
Copper
N ligands
Nickel
Schiff bases
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Summary:The chiral N4 Schiff bases (1R,2R)‐N,N′‐bis(2‐p‐tosylaminobenzylidene)‐1,2‐diaminocyclohexane (H2CyTs, 1), (1R,2R)N,N′‐bis(2‐trifluoromethylsulfonaminobenzylidene)‐1,2‐diaminocyclohexane (H2CyTf, 2), (1R,2R)‐N,N′‐bis(2‐aminobenzylidene)‐1,2‐diaminocyclohexane (3) and (1R,2R)‐N,N′‐bis(2‐nitrobenzylidene)‐1,2‐diaminocyclohexane (4) were synthesized by a new and easy method in high purity and good yields. All the organic compounds were characterized by elemental analysis, mass spectrometry, IR and 1H and 13C NMR spectroscopy. Divalent Co, Cu and Ni complexes 5−8, containing the sulfonamide ligands 1 or 2, have been prepared and characterized. The X‐ray crystal structures of complexes [Co(1R,2R)‐CyTs] (6) and [Ni(1R,2R)‐CyTf] (8) have been solved. These complexes are potential precursors for homogeneous asymmetric catalysis of a variety of reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200390182