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    Syntheses and complexes of new chiral heterocyclic ligands

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    Author
    Watson, Andrew A.
    Date
    1987
    Permanent Link
    http://hdl.handle.net/10092/8320
    Thesis Discipline
    Chemistry
    Degree Grantor
    University of Canterbury
    Degree Level
    Doctoral
    Degree Name
    Doctor of Philosophy

    The complexation properties of the chiral heterocyclic ligand (4S,7R)- 7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-1H(2H)-indazole (4) have been investigated and its site of coordination to transition metal ions has been established by n.m.r. spectroscopy and X-ray crystallography as occurring through the more hindered N1 nitrogen. N1, N2 and C3 substituted derivatives of 4 have been synthesised and characterised. These new compounds represent a diverse range of new chiral heterocyclic bidentate, tridentate and binucleating ligands. In total sixty two new ligands have been synthesised of which fifty are chiral. The complexation properties of the majority of these new ligands have been investigated. The structures of the following complexes have been determined by X-ray crystallography: [Cu(4)₂Cl₂] viz (8), a 4-coordinate copper complex with distorted tetrahedral geometry; [Pd(10)₂Cl₂] viz (11), a trans-dichloro palladium complex; [Pd(1 0)Cl]₂ viz (12), a chiral cyclopalladated complex; [Pd(28)Cl₂] viz (30), a cis-dichloro palladium complex; [Ni(33)₂(ClO₄)]ClO₄.EtOH viz (34), an octahedral nickel complex with a chelating bidentate perchlorate; [Pd(38)Cl₂] viz (39), a cis dichloro palladium complex; [Pd₂(42)₂Cl₄] viz (44), a chloro-bridged dimeric palladium complex; [Ni(61)₂](ClO₄)₂ viz (74) , an octahedral nickel complex and [Cu(71 )(NCS)₂] viz (75) , a five coordinate copper complex. The potential application of these new compounds in asymmetric catalysis is discussed.

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