1984
DOI: 10.1021/ja00332a041
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Photochemical reactions of nitroanthracene derivatives in fluid solutions

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Cited by 35 publications
(34 citation statements)
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“…Planarization of the NO 2 group with consequent loss of the twisted conformation would lead in fact to a less extended overlap of the p-atomic-orbital of the O-atom with the adjacent orbital of the aromatic ring. As well-documented in the literature [28] [29], the twisted conformation is an essential prerequisite for the NO 2 to nitrite photorearrangement responsible for the formation of 1. The consequence of the planarization is, in turn, reflected in the logical increase of biradical character of the n,p* triplet and in the consequent high ability of this latter to abstract H-atoms in the presence of a suitable H-donor.…”
mentioning
confidence: 86%
“…Planarization of the NO 2 group with consequent loss of the twisted conformation would lead in fact to a less extended overlap of the p-atomic-orbital of the O-atom with the adjacent orbital of the aromatic ring. As well-documented in the literature [28] [29], the twisted conformation is an essential prerequisite for the NO 2 to nitrite photorearrangement responsible for the formation of 1. The consequence of the planarization is, in turn, reflected in the logical increase of biradical character of the n,p* triplet and in the consequent high ability of this latter to abstract H-atoms in the presence of a suitable H-donor.…”
mentioning
confidence: 86%
“…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].…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
Section: Introductionmentioning
confidence: 99%