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Bispidine derivatives as molecular tools for studies of (-Allyl)palladium complexes: Ligand synthesis and analythical cpplications
Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
1998 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Determination of structural and stereochemical features of reaction intermediates in transition metal catalysed reactions is of central interest. Bispidine derivatives as ligands in (π-allyl)palladium complexes in combination with 1H NMR spectroscopy are shown to be useful tools for revealing structural characteristics of these reaction intermediates. As a support for the conclusions drawn from NMR investigations, X-ray crystallography and calculated structures were used.

Complexes of bispidine derivatives with varying substitution pattern and different pre-formed bis[(η3-allyl)palladium chloride] complexes were formed. The resulting complexes were analysed with 1H NMR spectroscopy, especially regarding the inter-ligand NOEs and the chemical shift effects due to anisotropic effects. It is shown that a large steric interaction between the aromatic systems of N,N'-diphenylated bispidine derivatives and various (π-allyl)palladium systems can be obtained. This steric interaction can be used for hindering rotation around C-C single bonds in (π-allyl)palladium ligands.

Furthermore, the nearness of the aromatic systems and the (π-allyl)palladium ligand give rise to anisotropic effects that, after quantification, can give information about the structure in such complexes. The inter-ligand NOEs can, in the case of a N,N-diphenyl substituted bispidine derivative, be used for assignment of relative configuration in a set of acyclic (π-allyl)palladium ligands. With a bispidine derivative carrying chiral substituents, the inter-ligand NOEs were used for assignment of absolute configuration of (π-allyl)palladium ligands.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis , 1998. , 43 p.
Series
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 375
Keyword [en]
Chemistry
Keyword [sv]
Kemi
National Category
Chemical Sciences
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-895ISBN: 91-554-4248-X (print)OAI: oai:DiVA.org:uu-895DiVA: diva2:172248
Public defence
1998-09-25, Svedberg lecture hall at the Institute of Chemistry, Uppsala University, Uppsala, 10:15
Available from: 1998-09-04 Created: 1998-09-04Bibliographically approved

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