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The synthesis of a phenanthridine from an aromatic schiff base by a photooxidative ring closure

โœ Scribed by M.P. Cava; R.H. Schlessinger

Publisher
Elsevier Science
Year
1964
Tongue
French
Weight
129 KB
Volume
5
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The conversion of stilbenes into phenanthrenes by an oxidative photochemical process has been the object of considerable study;' the related photochemical conversion of azobenzene to phenazone has also been described.2

We wish now to report the first example of an analogous synthesis of a phenanthridene from an aromatic Schiff base. Ultraviolet irradiation of Schiff base I (formed from cu-naphthylamine and o-naphthaldehyde)' in ethanol in the presence of air afforded, in 4O$ yield, the previously unreported dibenzo~,~]phenanthridene (II), m.p. 270ยฐ.

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