Nitrobiphenyls Dinitrobiphenyls

In DMSO as solvent and in the presence of nitrobenzene, aryl-de-diazoniation of the unsubstituted benzenediazonium ion leads mainly via meta substitution to 3-nitrobiphenyl, whereas in the case of the 4-nitrobenzenediazonium ion the formation of o- and -substituted products (2,4 -and 4,4 -dinitrobiphenyl) prevails (Gloor et al., 1972). 

Some subsequent discussion on compound 3 followed our original paper on this subject (N. Masciocchi, M. Bergamo, A. Sironi, Comments on the elusive crystal structure of 4-iodo-4 -nitrobiphenyl Chem. Comm, 1998,1347-1348 J. Hulliger, P. J. Langley, On intrinsic and extrinsic defect-forming mechanisms determining the disordered structure of 4-iodo-4 -nitrobi-phenyl Chem Comm, 1998, 2557-2558), but these papers, which describe the effects of small amounts of 4,4 -dinitrobiphenyl impurity in 3, only reinforce the idea of structures based on N02—I synthons. 

The triplet state of 4-nitrobiphenyl has been observed in laser flashed benzene solution (. max 540 nm, t 10 ns at room temperature) 32). 4-Nitrobiphenyl and 4,4 -dinitrobiphenyl have been photoreduced by sodium formate in buffered aqueous methanolic solution 43i>) 15% 4-aminobiphenyl and 11% 4,4 -azobi-phenyl as well as 49% 4-amino-4 -nitrobiphenyl and 20% 4,4 -(p-nitrophenyl)-azoxybenzene, respectively, could be isolated and identified by comparison with authentic samples. 

Soil Benzidine was added to different soils and incubated in the dark at 23 °C under a carbon dioxide-free atmosphere. After 1 yr, 8.3 to 11.6% of the added benzidine degraded to carbon dioxide primarily by microbial metabolism and partially by hydrolysis (Graveel et al, 1986). Tentatively identified biooxidation compounds using GC/MS include hydroxybenzidine, 3-hydroxybenzidine, 4-amino-4 -nitrobiphenyl, A(A -dihydroxybenzidine, 3,3 -dihydroxybenzidine and 4,4 -dinitrobiphenyl (Baird et al, 1977). Under aerobic conditions, the half-life was estimated to be 2 to 8 d (Lu et ah, 1977). 

A six-membered ring is formed in the reduction of 2-nitrobiphenyl-2 -carboxylic acid68 or 6,6 -dinitrobiphenyl-2,2 -dicarboxylic acid.69 In the former case a phenanthridine is formed, in the latter a 4,9-diazapyrene. Similarly, a seven-membered ring is obtained when 2-nitro-2 -isothiocyano-biphenyl (15) is reduced in acidic solution with the formation of 6-mercapto-dibenzo[d/]-l,3-diazepine 3-oxide (16)70 [Eq. (28)]. 

However, no significant effect was observed with other aromatic diluents such as tert-butyl benzene, 2,4-dinitrophenol, 2-nitrobiphenyl, or 2,2-dinitrobiphenyl (241). 

Amino-2-methyl-l-propanol in isolation of levopimaric acid, 46, 64 e-Amino- -nitrobiphenyl, by nitration of o-aminobiphenyl, 46,86 from o,/> -dinitrobiphenyl, 46, 88 AmiNO-2-PIIOPANONE, SEiaCABSAZONE HYDROCSIAtiaOE, 46,1 Ammonia, reaction with 3,4-dichloto-... 

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