P-Phenylhydroxylamine

P-Phenylhydroxylamine is formed when anUine is treated with a neutral reducing agent, e.g., zinc powder and aqueous ammonium chloride solution ... 

Nitrosobenzene may be obtained by the oxidation of P phenylhydroxylamine inth add dichromato solution at 0° ... 

Add 4 4 g. of recrystaUised p-phenylhydroxylamine to a mixture of 20 ml. of concentrated sulphuric acid and 60 g. of ice contained in a 1 litre beaker cooled in a freezing mixture. Dilute the solution with 400 ml. of water, and boil until a sample, tested with dichromate solution, gives the smell of quinone and not of nitrosobenzene or nitrobenzene (ca. 10-15 minutes). Neutralise the cold reaction mixture with sodium bicarbonate, saturate with salt, extract twice with ether, and dry the ethereal extract with anhydrous magnesium or sodium sulphate. Distil ofiF the ether p-aminophenol, m.p. 186°, remains. The yield is 4-3 g. 

The group of potential 0,N-two-center ligands includes oximes (>C=N-OH), as well as hydroxylamine NH2OH, and its derivatives. The iri -coordination of simple oximes and substituted hydroxylamines in d transition metal complexes was reported almost simultaneously in Russia [9] and elsewhere [42,43]. More speciflcally, it was found [9,44,45] that the flnal product of the reaction between tungsten (molybdenum) oxotetrafluoride and simple oximes and p-phenylhydroxylamine is a complex anion with the deprotonated organic ligand [M0F4L] (where M=Mo, W HL stands for acetoxime, acetaldoxime, benzal-doxime, 2- and 4-pyridinaldoxime, and p-phenylhydroxylamine). 

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