By double Diels–Alder reaction of 2H-pyran-2-one derivatives and maleic anhydride or N-substituted maleimide, substituted bicyclo[2.2.2]octenes can be prepared via elimination of a CO2 molecule. Bicyclo[2.2.2]octene derivatives containing maleic anhydride rings are interesting targets for further conversions with nitrogen nucleophiles. In this Diploma work I intended to investigate reactions that would introduce pyridine and other (hetero)aromatic amines to the bicycle skeleton, which would serve either as ligands for various transition metal cations or as halogen bond acceptors and would thus represent important structural fragments in the construction of new 2D and 3D molecular architectures.
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