The Chemistry of the Diazo Compounds

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NO (R denoting the metal)^ (2) Free phenylnitrosoamine, C 6 H 5 . NH. NO, does not exist, as a solution of its non-combining sodium salt, when acidified with acetic acid, immediately gives an azo-dyestuff with /J-naphthol.
(3) ^9-Nitrodiazobenzene appears to exist only in the nitrosoamine form, and its alkali salt does not exist in the ' oxime ' condition.
These conclusions, as will be shown, do not truly represent the course of the reactions (see p. 98).
In a paper published shortly after the
...appearance of Schraube and Schmidt's work, Bamberger stated that he had earlier discovered a derivative of /3-naphthylamme cor- H 98 CHEMISTRY OF THE DIAZO-COMPOUNDS responding to the formula C 10 H 7 . NH. NO, which did not couple with /3-naphthol, but did so after treatment with a mineral acid. * He considered that the influence of the latter was to effect a transformation into the isomeric diazo-compound, thus C 10 H 7 . NH. NO -> C 10 H 7 . N:N. OH.
Confirmation of this view was afforded by von Pechmann and Frobenius, who stated uhat the silver salt of ^-nitro- phenylnitrosoamine, when treated with methyl iodide, yielded an oxygen-ether of ^9-nitrodiazobenzene N0 2 .


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