Zincke found that the products obtained by coupling a diazonium salt with a-naphthol, and by condensing phenylhydrazine with a-naphthoquinone, were identical; whilst Meldola acetylated the azophenols, and split the acetyl products by reduction in acid solution, but obtained no satisfactory results.
Concentrated nitric acid attacks them violently, producing various oxidation products, but if the amino group be "protected" by being previously acetylated, then nitro derivatives are obtained.
Wohl forms the oxime and converts it into an acetylated nitrile by means of acetic anhydride and sodium acetate; ammoniacal silver nitrate solution removes hydrocyanic acid and the resulting acetate is hydrolysed by acting with ammonia to form an amide, which is finally decomposed with sulphuric acid.
The syn-aldoximes or treatment with acetyl chloride readily lose water and yield nitriles; the anti-aldoximes as a rule are acetylated and do not yield nitriles.
Glucoseoxime on warming with acetic anhydride is simultaneously acetylated and dehydrated, yielding an acetylated gluconitrile, which when warmed with ammoniacal silver nitrate loses hydrocyanic acid and is transformed into an acetyl pentose.