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Zinc complexes of chiral ligands obtained from methylbenzylamine

Condensation of S-methylbenzylamine with 2 equiv. of 2,4- tert-butylphenol yielded the chiral tridentate ligand 2H 2, which formed the dimetallic complex ( 2)(k-N,(μ-O) 2ZnEt)((μ-O) 2ZnEt), 3, upon reaction with ZnEt 2. Reaction of the chiral Schiff base ligand, 4H, obtained from condensation of sal...

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Bibliographic Details
Published in:Inorganic chemistry communications 2011-11, Vol.14 (11), p.1737-1741
Main Authors: Pastor, María Frutos, Whitehorne, Todd J.J., Oguadinma, Paul O., Schaper, Frank
Format: Article
Language:English
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Summary:Condensation of S-methylbenzylamine with 2 equiv. of 2,4- tert-butylphenol yielded the chiral tridentate ligand 2H 2, which formed the dimetallic complex ( 2)(k-N,(μ-O) 2ZnEt)((μ-O) 2ZnEt), 3, upon reaction with ZnEt 2. Reaction of the chiral Schiff base ligand, 4H, obtained from condensation of salicylaldehyde and S-methylbenzylamine, with ZnEt 2 yielded ( 4) 2Zn, 5, or ( 4)ZnEt, 6, respectively. Deprotonation of 4H with NaH afforded tetrameric {( 4)Na} 4, 7. Complexes 3, 5 and 7 were characterized by single crystal diffraction studies and tested as initiators in the polymerization of rac-lactide. Complexes 3 and 5 showed only low to moderate activity. All complexes yielded essentially atactic polymers with minor contents of heterotactic enchainment. Several zinc complexes with chiral ligands based on S-methylbenzylamine were synthesized and characterized by X-ray diffraction analysis. They proved to be active, but unselective catalysts for the polymerization of rac-lactide. [Display omitted] ► Synthesis and characterization of a new tridentate, chiral ligand. ► Synthesis and characterization of 3 chiral zinc complexes and one chiral sodium complex. ► X-ray diffraction studies on 3 of these complexes. ► Application of 3 of these complexes in rac-lactide polymerization.
ISSN:1387-7003
1879-0259
DOI:10.1016/j.inoche.2011.07.018