Dibenzo[c,h]cinnoline 5-oxide has been synthesised. The compound is not identical with the hydrogen peroxide oxidation product of dibenzo[c,h]cinnoline and the sodium sulphide reduction product of 1-nitro-2-o-nitrophenylnaphthalene, which must therefore be dibenzo[c,h]cinnoline 6-oxide, as previously supposed. Aside from steric interactions, electronic effects are made responsible for the exclusive formation of the 6-oxide in the latter two cases.
W. H. Poesche, J. Chem. Soc. C, 1966, 890 DOI: 10.1039/J39660000890
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