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Paper | Special issue | Vol 47, No. 2, 1998, pp.893-909
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)99
On the Chlorine Addition to the C(5)-C(6) Bridge and the N-Oxidation of 1,10-Phenanthroline

Róza Antkowiak and Wieslaw Z. Antkowiak*

*Facluty of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznán, Poland

Abstract

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.