Synthesis and characterization of a series of 4-methyl-1-[2-aryl-1-diazenyl]-1,4-diazepanes and 1,4-di-[2-aryl-1-diazenyl]-1,4-diazepanes

摘要

1-Methylhomopiperazine was coupled with a series of diazonium salts to afford the 4-methyl-l-[2-aryl-l-diazenyl]-l,4-diazepanes (6),a new series of triazenes.These compounds are,in the main,stable crystalline solids (some of the series are stable oils),and they have been characterized by ~1H and ~(13)C NMR spectroscopy,IR spectros-copy,and mass spectrometry.NMR assignments were determined by 2D NMR and variable-temperature NMR experiments and by comparison with model compounds.A second series of new compounds,namely,l,4-di-[2-aryl-l-diazenyl]-l,4-diazepanes (5),were prepared by coupling unsubstituted homopiperazine (1,4-diazepane) with 2 molar equivalents of the diazonium salt and were similarly characterized.The crystal and molecular structure of the parent member of this bis-triazene series (5,X=H) has been determined by single-crystal X-ray diffraction analysis.