Tetraphenylporphine‐sensitized photooxygenation of benzofuran derivatives 1 afforded the corresponding benzofuran dioxetanes 2 in good yields. Allylic hydroperoxides 3 were formed regioselectively from 2,3‐dimethyl‐substituted benzofurans as minor products, except in the case of the benzofuran 1d, which gave predominantly the hydroperoxide 3d. The relative reactivities of the benzofurans toward singlet oxygen depended on the nature of substituents at the C‐2 and C‐3 positions of the furan rings. The benzofuran dioxetanes 2 were strongly mutagenic in the Salmonella typhimurium strain TA 100, their mutagenicity depending on the type of substituents of the dioxetane and of the benzo rings.
We describe three biomonitoring studies in which hemoglobin (Hb) adducts were used as biochemical markers to assess indirectly the target dose of genotoxic chemicals. We monitored the exposure to 1,3-butadiene in occupationally exposed workers and in two control groups by analyzing the adducts formed by the reaction of the first activation product, butadiene monoepoxide, with the terminal valine of Hb; we also measured hydrolyzable adducts formed by the reaction of metabolically formed nitroso derivatives with Hb from five selected nitropolycyclic aromatic hydrocarbons (1-nitropyrene; 2-nitrofluorene, 3-nitrofluoranthrene, 6-nitrochrysene, and 9-nitrophenanthrene) in coke oven workers of different job categories and control workers of the same geographical area. We detected hydrolyzable adducts from monocyclic nitroarenes in blood from individuals living in a contaminated area where explosives had been produced and from controls. The contaminants considered were 2,4,6-trinitrotoluene; 2,4- and 2,6-dinitrotoluene; and 1,3-dinitrobenzene. Differences between groups were significant, but interindividual variation was great and back-ground exposures must be considered.
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