The photorearrangement of 2-nitrofuran and 2-nitropyrrole

Investigation of photoreaction for 2-nitrobenzofuran and its 3-methyl derivative

“…In their study, 2-nitrofuran was irradiated in methanol and produced 3-hydroxyimino-2-oxo-2,3-dihydrofuran [19][20]. An analogue photoproduct was produced from the photorearrangement of 2-nitropyrrole [19]. Moreover, irradiation of 3-methyl-2-nitrofuran caused rearrangement occurred at 5-position which produced 5-hydroxyimino-3-metylfuran-2 (5H)-one [20].…”

“…In the photoreactions of nitro-substituted aromatic heterocycles, R. Hunt and S. T. Reid specifically investigated the photorearrangements of fivemembered nitroheteroaromatic systems such as 2-nitrofuran and 2-nitropyrrole. In their study, 2-nitrofuran was irradiated in methanol and produced 3-hydroxyimino-2-oxo-2,3-dihydrofuran [19][20]. An analogue photoproduct was produced from the photorearrangement of 2-nitropyrrole [19].…”

“…While photosubstitution and photoredox reactions were well investigated [1][2][3][4][5][6][7][8][9][10][11][12], photodissociation and nitro-nitrite rearrangement reactions have not been completely elucidated [11][12][13][14][15][16][17][18][19][20][21][22][23][24]. This is due to the fact that nitronitrite rearrangements and photodissociation reactions have low reaction efficiencies, which makes it difficult to observe any of the short-lived reaction intermediates.…”

“…The photoreactions of nitro-substituted aromatic hydrocarbons have also been thoroughly examined [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][26][27][28]. In the photoreactions of nitro-substituted aromatic heterocycles, R. Hunt and S. T. Reid specifically investigated the photorearrangements of fivemembered nitroheteroaromatic systems such as 2-nitrofuran and 2-nitropyrrole.…”

“…In 2-nitrobenzofuran, the nitro group and aromatic ring are arranged in a coplanar conformation. Some investigations show that aromatic nitro compounds with a coplanar conformation undergo nitro-nitrite rearrangements [13,[17][18][19][20] Conversely, Y. Kitamura and T. Matsuura explained the photochemistry of a hindered nitrobenzene [24], 2,6-dialkyl-substituted nitrobenzene, by referring to the mechanism developed by Chapman et al Although nonsubstituted nitrobenzenes undergo photoreduction in hydrogen-donating solvent [1,2], their study shows that nitro-nitrite rearrangements can also occur with photoreduction if 2,4,6-trimethylnitrobenzene is irradiated in 2-propanol solvent.…”