Endogenous Carcinogenesis: Nitrate, Nitrite and N-Nitroso Compounds

Tannenbaum, Steven R.; Green, Laura C.; Luzuriaga, Katherine R. de; Gordillo, Guido; Ullman, Lori; Young, Vernon R.

doi:10.1007/978-94-009-9104-0_23

Cited by 5 publications

(3 citation statements)

References 12 publications

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“…-The interest in the chemistry of nitrosooxy compounds and nitrosamines has gradually increased during the last ten years, not only because of their high carcinogenicity [ 1] [2] but also because of their usefulness as reagents for organic synthesis 131. Their reaction behavior, which has been studied under a variety of conditions, involves in a number of cases an intramolecular rearrangement.…”

Section: Discussionmentioning

confidence: 99%

“…Assuming the photolytic transformations to occur analogously to those of the above discussed examples (Eqn. [2][3][4], the complex partner of nitroxyl is pyrrolidineimine. We have not attempted to analyze the complex IR spectrum of the imine, but the strong absorption at 1636.5 cm-' is considered to signify a C=N functional group (e.g.…”

Section: Many Absorptions Of B Overlap With Absorptions Of Amentioning

confidence: 99%

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HNO, an Intermediate in (Light‐induced) Rearrangement Reactions of Nitrosooxy Compounds and Nitrosamines

Müller

Murata

Nonella

et al. 1984

Helvetica Chimica Acta

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IR‐spectroscopic investigations of light‐induced rearrangement reactions of nitrosooxymethane (CH3ONO3), nitrosooxyethane (CH3CH2ONO) and N,N‐dimethylnitrosamine ((CH3)2NNO) in low‐temperature rare‐gas matrices have established that these molecules are transformed in two photolysis steps to the previously unknown C‐nitroso compounds nitrosomethanol (CH2(OH)(NO)), 1‐nitrosoethanol (CH3CH(OH)(NO)), and methyl(nitrosomethyl)amine CH2(NO)(NH)(CH3). Evidence for a similar rearrangement reaction has been advanced for N‐Nitrosopyrrolidine which is converted to C‐nitrosopyrrolidine . The matrix‐isolation technique in combination with wavelength‐selective irradiation allowed to trap and characterize an intermediate of rearrangement which revealed to be nitroxyl (HNO) complex (CH2…HNO, CH3CHO…HNO, CH3N = CH2…HNO, and ). Since these findings have a close resemblance with rearrangement reactions of more complex nitrosooxy compounds, nitrosamines, or nitrosohydrazines used in organic synthesis, it is suggested that also in these reactions nitroxyl is present as an intermediate species.

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Section: Discussionmentioning

confidence: 99%

Section: Many Absorptions Of B Overlap With Absorptions Of Amentioning

confidence: 99%

HNO, an Intermediate in (Light‐induced) Rearrangement Reactions of Nitrosooxy Compounds and Nitrosamines

Müller

Murata

Nonella

et al. 1984

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…Rearrangement reactions of nitroso compounds of higher molecular weight are important since these molecules are widely used in synthetic organic chemistry [20,21]. The discovery of the high carcinogenicity of many nitroso compounds has ultimately placed these substances and their possible reaction mechanisms into the view of a wider audience [22,23].…”

Section: Rearrangement R_eactions Of Nitroso Compoundsmentioning

confidence: 99%