Triazene

About: Triazene is a research topic. Over the lifetime, 759 publications have been published within this topic receiving 8714 citations. The topic is also known as: Triazene cleavage & 1-triazene.

Preparation of Glycosyltriazenes

Abstract: O-Unprotected glycosyltriazenes are prepared for the first time by coupling of 1-anthraquinone-1-diazonium hydrogensulfate with β-glycopyranosylamines to afford 1- (anthraquinone-1-yl)-3-( β-glycopyranosyl)triazenes 3a—h. Acetylation of compounds 3 furnished the O-acetates 4a—g. The stability of triazenes 3 results from fixation of the NH proton in an intramolecular hydrogen bond to one of the anthraquinone carbonyl oxgen atoms. Treatment of triazenes 4 with tert-butyl hypochlorite afforded acetoglycosyl chlorides 6 and 1-azidoanthraquinone 7. With acetic acid the triazene 4a formed tetra-O-acetyl-D-xylopyranose 9 together with 1- aminoanthraquinone 10.

Crystal Structure of 1-(4-Bromophenyl)-3-(4-nitrophenyl)triazene

Abstract: The crystal structure of the title compound, C12H9BrN4O2, shows that the stereochemistry about the N=N double bond in the diazoamine moiety is trans. The dihedral angle [6.7(6)°] between the terminal phenyl rings indicates that the whole molecule is almost planar (r.m.s. deviation = 0.0945 A). Intermolecular N-H…O and C-H…O hydrogen bonds generate infinite one-dimensional linear chains along the [0 0 1] direction. The unequal distribution of the double-bond character among the N atoms of the diazoamine moiety indicates a delocalization of the π electrons over the N=N-N(H) moiety towards the terminal aryl substituents.