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• W2065267492 abstract "Several singlet nitroso oxides (3a−e) were generated by the thermal reaction of triplet nitrenes (2a−e) with triplet oxygen at 95 K in 2-methyltetrahydrofuran. After photolysis of the nitroso oxides at 77 K using strong light intensities, the formation of intermediates was observed for the first time. From spectroscopic, kinetic, and chemical arguments, we postulate the formation of the following dioxaziridines: 4-(dioxaziridin-yl)stilbene (4a), 4-(dioxaziridin-yl)-4‘-nitrostilbene (4b), 4‘-(dioxaziridin-yl)-4-(dimethylamino)stilbene (4c), 4‘-(dioxaziridin-yl)-4-aminobiphenyl (4d), and 4-(dioxaziridin-yl)-4‘-(nitrene-substituted)stilbene (4f). All dioxaziridines observed are highly reactive species. At 77 K, they react thermally to form the corresponding nitro compounds (5). The velocity of the ring opening reaction of the dioxaziridines (4 → 5) is not significantly influenced by substituents; the rate constants at 77 K are all equal to 0.0030 ± 0.0005 s-1. The transients were characterized by stationary UV/vis and/or ESR spectroscopy. Ab initio calculations of the thermal reaction of the nonsubstituted dioxaziridine (6) and N-phenyldioxaziridine (9) were performed. From this, it follows that dioxaziridines are experimentally observable species which are separated from the corresponding nitro products by an orbital symmetry-forbidden barrier." @default.
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• W2065267492 date "1999-06-30" @default.
• W2065267492 modified "2023-10-03" @default.
• W2065267492 title "Photochemical Reactions of Nitroso Oxides at Low Temperatures: The First Experimental Evidence for Dioxaziridines" @default.
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• W2065267492 doi "https://doi.org/10.1021/ja9803660" @default.
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