1979
DOI: 10.1139/v79-478
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Generation of aminyl and aminium radicals by photolysis of N-nitrodialkylamines in solution

Abstract: Photolysis of nitramines in a neutral solvent generated nitrogen dioxide and aminyl radicals which abstracted a hydrogen but did not add to a π-bond. In dilute acidic solution, the aminyl radicals generated from the photolysis were protonated to the corresponding aminium radicals that preferentially added to π-bonds rather than abstracted a hydrogen. However, complex mixtures of addition products were obtained when nitramines were photolysed in the presence of cyclohexene under nitrogen. The plethora of the pr… Show more

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Cited by 11 publications
(5 citation statements)
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“…As in the present study, photoaddition products of N -nitrodialkylnitramines and cyclohexene were not obtained. The photolysis is explained by Chow et al by a radical mechanism where in an initial step homolytic cleavage of the N−N bond generates nitrogen dioxide and the aminyl radical, which could undergo further reactions. N−N bond cleavage can also be assumed during the photolysis of 1 resulting in 5 by hydrogen transfer from the organic solvents ( Scheme ).…”
Section: Resultsmentioning
confidence: 99%
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“…As in the present study, photoaddition products of N -nitrodialkylnitramines and cyclohexene were not obtained. The photolysis is explained by Chow et al by a radical mechanism where in an initial step homolytic cleavage of the N−N bond generates nitrogen dioxide and the aminyl radical, which could undergo further reactions. N−N bond cleavage can also be assumed during the photolysis of 1 resulting in 5 by hydrogen transfer from the organic solvents ( Scheme ).…”
Section: Resultsmentioning
confidence: 99%
“…A possible intermediate in the formation of 2 is N -nitrosoimidacloprid ( 6 ). Nitrosamines are described as main photoproducts of nitramines , and during irradiation of 1 on leaves of tomato plants, Scholz and Reinhard observed 6 as one of four main photoproducts. But, during the irradiations of 1 in our solvent systems, 6 could not be identified as photoproduct.…”
Section: Resultsmentioning
confidence: 99%
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“…Formation of formaldehyde and N -methyl- N -nitrosoaniline from thermolysis of the N -nitroaniline 1 with N , N -dimethylaniline can be rationalized as depicted in Scheme 8.
…”
Section: Resultsmentioning
confidence: 99%
“…After irradiation (2.5 h), the photolysate was concentrated to 30 ml and water (50 ml) was added. The mixture was then extracted with ether (3 x 40 ml). The ether extract was washed with water (2 x 30 ml), dried, and evaporated to give an oil (440 mg) which showed no n.m.r.…”
Section: Discussionmentioning
confidence: 99%