Thermal and photolytic cyclisation, rearrangement, and denitration reactions of o-nitro-t-anilines

Photolysis of the herbicide dinitramine (N3,N3-diethyl-2,4-dinitro-6-trifluoromethyl-m-phenylenediamine)

“…The appearance of a ring-closed product from photolysis of nitro-substituted diamine or aniline herbicides has not been observed heretofore. Under somewhat different conditions, however, the acid-catalyzed photolysis of o-nitrophenyl derivatives of cyclic amines has been reported to form benzimidazoles (Fielden et al, 1970).…”

Photochemistry of bioactive compounds. Multiphase photodegradation of basalin

“…The formation of the benzimidazole products was not unexpected. Previous studies have shown that iV-alkyl-onitroanilines are readily converted to benzimidazoles and benzimidazole N-oxides upon irradiation at 2537 Á (Neadle and Pollitt, 1967) and upon irradiation through Pyrex (Fielden et al, 1970, and references therein). The entire aspect of o-nitroarylamine interactions has been the subject of a recent review by Preston and Tennant (1972).…”

Photocatalytic Degradation of Trifluralin, Clodinafop-Propargyl, and 1,2-Dichloro-4-Nitrobenzene As Determined by Gas Chromatography Coupled with Mass Spectrometry

“…11, and 12) and benzimidazole-N-oxide derivative 7 was not unexpected. Previous studies have shown that N-alkyl-o-nitroanilines are readily cyclised to form benzimidazoles and benzimidazole-N-oxides upon irradiation at 2537Å and upon irradiation through Pyrex [41,42]. The entire aspects of chemical interaction between aromatic nitro groups and ortho side chains had been the subject of a review by Preston and Tennant [43].…”