206535-75-3Relevant academic research and scientific papers
On the chlorine addition to the C(5)-C(6) bridge and the N-oxidation of 1,10-phenanthroline
Antkowiak, Roza,Antkowiak, Wieslaw Z.
, p. 893 - 909 (2007/10/03)
It was found that under the influence of aqueous hypochlorite 1,10-phenanthroline (1) is initially transformed into 5,6-dichloro-5,6-dihydro-1,10-phenanthroline (2) and 5-chloro-6-hydroxy-5,6-dihydro-1,10-phenanthroline (8). The latter readily undergoes subsequent transformations either into a mixture of 5,5-dichloro-6-oxo-5,6-dihydro-1,10-phenanthroline (4) and 5,6-dioxo-5,6-dihydro-1,10-phenanthroline (5) or into the known 5,6-epoxy-1,10-phenanthroline (3) depending on the acidic or alkaline conditions, respectively. In contrast to the flat molecule of the starting 1, that of the dichloro derivative (2) being twisted at the central bond of the bipyridine system can be easily N-oxidized to di-N-oxide (11). Both 2 and its di-N-oxide (11) in the presence of sodium isopropoxide at 0°C freely lost hydrogen chloride and returned to the fully aromatic system of 5-chloro-1,10-phenanthroline (9) and its di-N-oxide (13), respectively.
