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Photochemical Isomerization of 4H-Imidazole N-Oxides and N,N-Dioxides
Nechepurenko,Petrenko,Grigor'ev,Volodarskii
, p. 705 - 709 (2007/10/03)
Photolysis of 4H-imidazole 3-oxides and 1,3-dioxides yields oxaziridines: 6-oxa-1,4-diazabicyclo-[3.1.0]hex-3-enes and corresponding 4-oxides, which undergo fast thermal isomerization into initial N-oxides. Further photolysis of 6-oxa-1,4-diazabicyclo[3.1.0]hex-3-ene 4-oxides yields mixtures of stereoisomeric cis-and trans-3,7-dioxa-1,4-diazatricyclo[4.1.0.02,4]heptanes; only the cis isomers are capable of thermal isomerization into initial 4H-imidazole 1,3-dioxides.
