Chemical Constitution, Electrochemical, Photographic and Allergenic Properties of p-Amino-N-dialkylanilines<sup>1</sup>

Bent, R. L.; Dessloch, J. C.; Duennebier, Fred C.; Fassett, David W.; Glass, Dudley B.; James, T. H.; Julian, D; Ruby, W. R.; Snell, John M.; Sterner, James H.; Thirtle, John R.; Vittum, Paul W.; Weißberger, A.

doi:10.1021/ja01151a037

Cited by 82 publications

(9 citation statements)

References 4 publications

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“…The substituents on the N-alkyl group of CD-3 and CD-4 apparently also lower the oxidation potential of these molecules. These results are in agreement with results achieved at the strongly alkaline pH characteristic of colour film developing processes (21). Although the investigated compounds show small differences in the Eax 112 values, these small differences can be of importance in a complex in vivo activation.…”

Section: Discussionsupporting

confidence: 91%

Concomitant contact dermatitis due to textile dyes and to colour film developers can be explained by the formation of the same hapten

1997

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p-phenylenediamine derivatives are widely used in industry and in cosmetics, and several of them are well-known sensitizers. One group of allergenic p-phenylenediamine derivatives are used as colour film developers. Cross-reactivity between the colour film developers has been reported. In this paper, an occupational facial dermatitis due to colour film developers is described. The patient reacted to colour film developers (CD-1, CD-2, CD-3, and CD-4), but not to other p-phenylenediamine derivatives tested. He also showed allergic reactions to Disperse Blue 106 and Disperse Blue 124 and to Disperse Red 17, but not to Disperse Orange 3. The activation of the colour film developers by oxidation at physiological pH was analysed with chemical methods, and the mechanism responsible for the concomitant reactivities to the colour film developers and the disperse dyes at a molecular level is discussed.

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Section: Discussionsupporting

confidence: 91%

Concomitant contact dermatitis due to textile dyes and to colour film developers can be explained by the formation of the same hapten

1997

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“…Caled for CuH18N2: C, 74.16; H, 10.11; N, 15.73. Found: C, 74.0; H, 10.35; N, 15.82. AT- ethyl)propionamide (24). n-Dibutylamine (13.1 g, 100 mmol), 10.1 g (100 mmol) of 7, and 300 mg of zinc acetate were allowed to react at 180 °C for 24 h in a pressure reactor.…”

Section: Methodsmentioning

confidence: 99%

Nucleophilic ring opening of 2-oxazolines with amines: a convenient synthesis for unsymmetrically substituted ethylenediamines

Fazio¹

1984

J. Org. Chem.

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“…61 The hydrazones were also prepared by a literature method. 62 Other compounds: N-ethyl-N-methyl-4-nitrosoaniline 22, 63 N-ethyl-N-methyl-2-nitroaniline 23, 64 N-ethyl-N-methyl-2,4-dinitroaniline 18, 65 N-ethyl-N-methyl-4chloro-2-nitroaniline 33. 66…”

Section: Synthesismentioning

confidence: 99%

The mechanistic origin of regiochemical changes in the nitrosative N-dealkylation of N,N-dialkyl aromatic amines

Teuten

Loeppky

2005

Org. Biomol. Chem.

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The regioselectivity of the nitrous acid mediated dealkylation of 4-substituted-N-ethyl-N-methylanilines is a function of the acidity of the reaction mixture. At high acidity deethylation predominates, whereas demethylation is the predominant reaction in nitrosamine formation at pH 2 and above. In some cases the regioselectivity of nitrosative dealkylation changes as the run proceeds. Through the use of the corresponding 4-nitroaniline as the primary substrate, CIDNP, kinetics, kinetic deuterium isotope effects and other transformations involving nitrosations with NO2 or NOBF4 in aprotic solvents, a new mechanism of tertiary amine nitrosation has been deduced and proposed to explain regioselective deethylation. The mechanism involves the oxidation of the substrate to the amine radical cation by NO+. This is followed by the abstraction of a hydrogen atom from the carbon adjacent to the amine nitrogen by NO2 to produce an iminium ion which reacts further to produce the corresponding aldehyde and the nitrosamine. Depending upon the acidity, this process competes with three other mechanistic pathways, two of which give the nitrosamine through the iminium ion, and one leads to the formation of C-nitro compounds. The competing pathways to nitrosamine formation involve NOH elimination from a nitrosammonium ion and deprotonation of the radical cation to give an alpha-amino radical which rapidly oxidized to the iminium ion. Predominant, but not highly regioselective demethylation occurs by these pathways. Nitro compound formation principally arises from the reaction of NO2 with the radical cation followed by deprotonation, but also occurs by para C-nitrosation followed by oxidation.

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Chemical Constitution, Electrochemical, Photographic and Allergenic Properties of p-Amino-N-dialkylanilines¹

Cited by 82 publications

References 4 publications

Concomitant contact dermatitis due to textile dyes and to colour film developers can be explained by the formation of the same hapten

Concomitant contact dermatitis due to textile dyes and to colour film developers can be explained by the formation of the same hapten

Nucleophilic ring opening of 2-oxazolines with amines: a convenient synthesis for unsymmetrically substituted ethylenediamines

The mechanistic origin of regiochemical changes in the nitrosative N-dealkylation of N,N-dialkyl aromatic amines

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Chemical Constitution, Electrochemical, Photographic and Allergenic Properties of p-Amino-N-dialkylanilines1

Cited by 82 publications

References 4 publications

Concomitant contact dermatitis due to textile dyes and to colour film developers can be explained by the formation of the same hapten

Concomitant contact dermatitis due to textile dyes and to colour film developers can be explained by the formation of the same hapten

Nucleophilic ring opening of 2-oxazolines with amines: a convenient synthesis for unsymmetrically substituted ethylenediamines

The mechanistic origin of regiochemical changes in the nitrosative N-dealkylation of N,N-dialkyl aromatic amines

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Chemical Constitution, Electrochemical, Photographic and Allergenic Properties of p-Amino-N-dialkylanilines¹