Aminofluorene following oxidation

TABLE II. DNA OR POLYRIBONUCLEOTIDE ADDUCT FORMATION WITH AMINOFLUORENE FOLLOWING OXIDATION BY PEROXIDES... 

Schemes 24 and 34. Not all specific examples follow these generalized pathways. Although 78h does decompose predominately into 99 (Scheme 44) at neutral pH, evidence suggests that it may not do so via an addition-elimination mechanism. This intermediate is detectable in reaction mixtures, but it has never been isolated due to its high reactivity. The N-benzoyl analogue 78h has been prepared by anodic oxidation of N-benzoyl-2-aminofluorene and has been shown by labeling experiments to generate 99 by an intramolecular pathway presumably involving the intermediate 100. ...

We previously compared the properties of the reactive species involved in DNA binding by N-OH-aminofluorene, N-acetoxy-acetyl-aminofluorene and the aminofluorene products formed by a peroxidase catalyzed oxidation (28). The marked differences in reactivity suggested that different species were involved and that nitrenium ions were not responsible for the peroxidase catalyzed activation. The identity of the products formed following a peroxidase catalyzed oxidation is still not clear. Other investigators have shown the formation of nitrofluorene and azofluorene but most of the... 

---