Ring-degenerate rearrangement resulting from the azo coupling reaction of a 3-aryl-1,3a,6a-triazapentalene

The 3-(4-(methoxycarbonyl)phenyl)triazapentalene is a highly fluorescent small molecule which is readily accessible via a two-step synthesis. In the search for postfunctionalization methods, a radical CH-arylation with diazonium salts was attempted. However, azo coupling resulted in a ring-degenerate rearrangement toward a 2-aryl-4-azotriazapentalene, which was confirmed via crystallographic analysis. A mechanism involving the generation of a nitrilimine is proposed. In addition, reduction of the azo group led to cleavage of the triazapentalene core. The present results further demonstrate the sensitivity of the triazapentalene fluorophore.

Publication year:2020

BOF-keylabel:yes

IOF-keylabel:yes

BOF-publication weight:2

CSS-citation score:1

Authors from:Higher Education

Accessibility:Open