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AROMATIC NITRO COMPOUNDS 195

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According to that author, such a typical aromatic nitro compound as 4-nitro-

l-naphthol (VII) when reacted with diazomethane, formed not only methyl ether

(VIII) but also quinone oxime (IX) in lower yield (16%):

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VII VIII IX

From these examples one could infer that diazomethane would react with those

nitro compounds which contain a reactive hydrogen atom. With that respect

particularly important is recent work of de Boer [160].

The nitro group can take part in the formation of heterocyclic nitrogen-

containing rings. For example, one of the well known methods for the preparation

of phenazine derivatives consists in heating derivatives of 2-nitro-2’-aminodiphenyl-

amine at high temperature (Kehrmann et al. [11]) :

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The synthesis of phenazine derivatives and phenazine oxide based on the con-

densation of aromatic nitro compounds with aromatic amines in an alkaline medium

(sodium hydroxide), reported for the first time by Wohl [12] in 1901, was of simi-

lar character :

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