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Easy Synthesis of New Chiral Tetradentate N 4 Schiff Bases and Their Use as Ligands for Metal Complexes
Author(s) -
Karamé Iyad,
Tommasino M. Lorraine,
Faure René,
Lemaire Marc
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390182
Subject(s) - chemistry , sulfonamide , crystal structure , metal , nuclear magnetic resonance spectroscopy , catalysis , divalent metal , homogeneous catalysis , enantioselective synthesis , stereochemistry , schiff base , medicinal chemistry , divalent , transition metal , crystallography , organic chemistry
The chiral N 4 Schiff bases (1 R, 2 R )‐ N , N ′‐bis(2‐ p ‐tosylaminobenzylidene)‐1,2‐diaminocyclohexane (H 2 CyTs, 1 ), (1 R, 2 R ) N , N ′‐bis(2‐trifluoromethylsulfonaminobenzylidene)‐1,2‐diaminocyclohexane (H 2 CyTf, 2 ), (1 R, 2 R )‐ N , N ′‐bis(2‐aminobenzylidene)‐1,2‐diaminocyclohexane ( 3 ) and (1 R, 2 R )‐ 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 1 H and 13 C 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(1 R, 2 R )‐CyTs] ( 6 ) and [Ni(1 R, 2 R )‐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)