Photochemical studies. VI. Photochemistry of nitrobenzoate esters and related nitroaromatic compounds. Some novel reduction and esterification reactions

Comparison of photoreactions of flutamide in acetonitrile and 2-propanol solvents in the absence of cage-forming compounds

“…They showed, using gas chromatography, that the formation of acetone during the photoreduction reaction was evidence of hydrogen being abstracted from 2-propanol. It has been reported that the photoreduction of aromatic nitro compounds, including the hydrogen abstraction process, occurs in some alcoholic solvents, such as 2-propanol and ethanol [2][3][4]11].…”

“…Aromatic nitro compounds are known to undergo various photoreactions, such as photosubstitution, photoredox reactions, photodissociation and photo-induced nitro-nitrite rearrangement [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. Photosubstitution and photoredox reactions have been well investigated [1][2][3][4][5][6][7][8][9][10][11], but photodissociation and nitro-nitrite rearrangement have not yet been fully elucidated [10][11][12][13][14][15][16][17].…”

“…Photosubstitution and photoredox reactions have been well investigated [1][2][3][4][5][6][7][8][9][10][11], but photodissociation and nitro-nitrite rearrangement have not yet been fully elucidated [10][11][12][13][14][15][16][17]. Nitro-nitrite rearrangement and photodissociation have low reaction efficiencies, and the short-lived intermediates of these reactions are difficult to observe.…”

“…Likewise, Sortino et al suggested that the nitro-nitrite rearrangement of flutamide is the only photoreaction that will occur in a homogeneous solution, such as in methanol or 2-propanol [21]. It is surprising that nitro-nitrite rearrangement occurred as a single photoreaction in a homogeneous solution because there are a wide variety of photoreactions of aromatic nitro compounds, including photoredox reactions, photosubstitution, and photodissociation [1][2][3][4]. The occurrences of these reactions of flutamide in different media have been insufficiently investigated; hence, the photoreactions of flutamide need to be further studied to obtain more experimental data.…”

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

“…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.…”