Phenazine N-oxide

W 0 H L - A U E Phenazine synthesis Synthesis of phenazine N-oxide from anilines and nitrobenzene... 

Proximity effects and ortho interactions in 2,2/-disubstituted diaryl amines have been reported104. Thus, phenazine, phenazine-N-oxide and carbazole were formed by loss of small neutral fragments, such as NO, NO2 and NO3, from the molecular ions, as illustrated by the formation of carbazole from 2,2/-dinitrodiphenylamine see Scheme 34. Of particular interest is the loss of NO3, as demonstrated by high-resolution MS data and metastable ion spectra104. 

Dicarboxy-phenazine-N-oxide 5 D1202—D1203 l,9-dicarboxy-2,4,6,8-tetranitrophenazine-N-oxide 5 D1202-D1203... 

In the case of substituted phenazine N-oxides some activation of substituents towards nucleophilic substitution is observed. 1-Chlorophenazine is usually very resistant to nucleophilic displacements, but the 2-isomer is more reactive and the halogen may be displaced with a number of nucleophiles. 1-Chlorophenazine 5-oxide (56), however, is comparable in its reactivity with 2-chlorophenazine and the chlorine atom is readily displaced in nucleophilic substitution reactions. 2-Chlorophenazine 5,10-dioxide (57) and 2-chlorophenazine 5-oxide both show enhanced reactivity relative to 2-chlorophenazine itself. On the basis of these observations, similar activation of 5- or 6-haloquinoxaline iV-oxides should be observed but little information is available at the present time. 

Scheme 11.2. Isomer distribution in miration of phenazine N-oxide.

WAAC Women s Army Auxiliary phenazine-N-oxide)... 

Dicarboxy-phenazine-N-oxide, Ci4H4Ng03, may be assumed to be the parent eompd of its tetranitro deiiv although it was not used to prep it ... 

Phenanzin-N-oxid wird in quantitativer Ausbeute mit Hydrazin und Palladium/Kohle zu Phenazin reduziert4. Analog entsteht aus 2-Chlor-phenazin-N-oxid mit Ruthe-nium/Kohle und Hydrazin ohne Enthalogenierung l-Chlor-phenazin3. 

Developments in quinoxaline chemistry during the period 1963—1975 have been reviewed, as have recent advances in the chemistry of phenazine N-oxides. ... 

A photochemical synthesis of N-oxides, that of phenazine N-oxides from acylated o-nitrodipheny-lamines, has also been reported. ... 

Albini, A., Bettinetti, G., and Pietra, S., Photoisomerization of substituted phenazine N-oxides, Gazz. Chim. Ital, 105, 15, 1975. 

Fasani, E., Pietra, S., and Albini, A., The photocycHzation of N-acyl-2-nitrodiphenylamines to phenazine N-oxides, Heterocycles, 33, 573,1992. 

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