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1,4,5,8‐Tetra‐Azaphenanthrene Complexes of Copper(I) and Silver(I)

par Nasielski, Jacques ;Hinkens, Raymonde ;Heilporn, Sylvie ;Rypens, C.;Declercq, Jean-Paul
Référence Bulletin des Sociétés chimiques belges, 97, 11-12, page (983-992)
Publication Publié, 1988

Article révisé par les pairs

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Résumé :

Cu(l) and Ag(l) complexes of 1,4,5,8‐tetra‐azaphenanthrene (TAP) and of two of its methylated derivatives (3,6‐dimethyl‐ and 2,3,6,7‐tetramethyl‐) have been made and characterized. Their HNMR spectra are discussed. The structure of the complex Ag(TAP)2(NO3), as determined by X‐Ray crystallography, is that of a strongly folded and twisted square planar arrangement of the chelating ligands around the silver atom; the four Ag‐N bonds are not equal: they are shorter (2.36 Å) in one pair of trans bonds than in the other (2.56 Å). 3,6‐Dimethyl‐1,4,5,8‐tetra‐azaphenanthrene (3,6dmTAP), a new TAP derivative, has been synthesized starting from 2‐hydroxy‐3‐methylquinoxaline which was nitrated, then treated with POCl3, the resulting 2‐chloro‐3‐methyl‐6‐nitroquinoxaline reacted with hydrazine and the hydrazino group oxidized to give 3‐methyl‐6‐nitroquinoxaline. This was aminated with hydroxylamine, reduced to the diamine and finally condensed with glyoxal to give 2,6‐dimethyl‐ and 3,6‐dimethyl‐1,4,5,8‐tetra‐azaphenanthrene. Copyright © 1988 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim