Nitrodiphenyl ethers

A yield of 84 per cent of u-nitrodiphenyl ether boiling at i83-i85°/8 mm. is obtained when o-nitrochloro benzene is used. For the preparation of j-nitro diphenyl ether, the method of Ullmann and Sponagel, using m-bromonitrobenzene, seems to be the best, since m-chloro nitrobenzene gives large amounts of tarry matter. 

Nitrodiphenyl ether has been prepared by heating p-nitro-chlorobenzene with potassium phenoxide and phenoD and by the nitration of diphenyl ether. ... 

Nitrodiphenyl ether, 14, 67 2-Nitrodiphenyl ether, 14, 67 p-NlTRODIPHENYL ETHER, 14, 66... 

Nitrodiphenyl ether, 3472 mixo-Nitroindane, 3140 4-Nitroisopropylbenzene, 3157 Nitromesitylene, 3158... 

Dichloro-4 -nitrodiphenyl ether, see Bifenox Dichloronitromethane, see Chloropicrin... 

Photolytic. The UV photolysis (7, = 300 nm) of bifenox in various solvents was studied by Ruzo et al. (1980). In water, 2,4-dichloro-3 -(carboxymethyl)-4 -hydroxydiphenyl ether and 2,4-di-chloro-3 -(carboxymethyl)-4 -aminodiphenyl ether were identifled. In cyclohexane, 2,4-dichloro-4 -nitrodiphenyl ether and methyl formate were the major products. In methanol, a dichloro-methoxy phenol was identified. Photodegradation occurred via reductive dechlorination, de-carboxymethylation, nitro group reduction, and cleavage of the ether linkage (Ruzo et al., 1980). 

C j 4 alkyl group) 0.5—8.0%, and binder 15—45%. The binder contains 15—45% polymeric material, such as poly (vinyl acetate) or polyfvinyl chloride) with the lower alkyl esters of NC and 65— 85% oxygenated hydrocarbon plasticizers (such as lower alkylene glycols their oxalates, maleates, diglycolates or nitrodiphenyl ethers, etc). E.g. AN 78, Prussian Blue 3, N-amino-alkylmorpholine 3) binder 12, carbon black 3 MgO I%]... 

Among the more recent approaches to phenoxazines and phenothiazines the reductive cyclization of 2-nitrodiphenyl ethers and sulfides with trialkyl phosphites is the most interesting. Here too a spiro intermediate is involved, produced by attack of an initially formed aryl nitrene on the second aromatic ring. The sulfide (252), for example, reacts with triethyl phosphite to yield 1-methylphenothiazine (253) and it is clear that in this case ring opening of the spiro intermediate also proceeds with a rearrangement of the Smiles type (Scheme 113) (75JCS(P1)2396). 

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