Synthesis and characterization of a novel chiral azomethine diselenide

The first chiral diselenide 9 having an ortho-azomethine functional group has been synthesized by the reaction of bis(o-formylphenyl) diselenide with the chiral amine R(+)-(1-phenylethylamine). The chiral diselenide 9 was further characterized by derivatizing it into the corresponding selenenyl halides. The derivatives are characterized by single crystal X-ray diffraction studies. In the solid state, the bromide derivative 11 shows the strongest Se⋯N intramolecular interaction. The chiral azomethine diselenide 9 has been further reduced to afford the diselenide 13. The monoselenide analogues of 9 and 13 have also been synthesized.

Graphical abstractThe condensation of bis(o-formylphenyl) diselenide with (R)-(+)-1-phenylethylamine afforded a novel chiral azomethine diselenide 9. The diselenide 9 was further characterized by derivatising it into the corresponding selenenyl halide derivatives. The crystal structure of the halide derivatives have been solved which show strong Se⋯N interactions.Figure optionsDownload full-size imageDownload as PowerPoint slide