C-nitroso compounds—VI

Mackor, A.; Wajer, Th. A. J. W.; Boer, Th. J. de

doi:10.1016/s0040-4020(01)82469-8

Cited by 117 publications

(35 citation statements)

References 13 publications

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“…The irradiation time was about 5 minutes. In all cases, a spectrum composed of a sharp triplet was recorded, and it was assigned to acyl radicals in view of the characteristically small hyperfine splittings of the nitrogen of the nitroxyl group (6). The results of these experiments are summarized in Table 1.…”

Section: IImentioning

confidence: 99%

Spin-trapping with 2-methyl-2-nitrosopropane: photochemistry of carbonyl-containing compounds. Methyl radical formation from dimethyl sulfoxide

Rosenthal¹,

Mossoba²,

Riesz³

1982

Can. J. Chem.

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The photochemical reactions of several carbonyl-containing compounds investigated by spin-trapping with 2-methyl-2-nitrosopropane revealed different modes of scission depending on the structure of the initial compound. Thus, in photo-Fries rearrangements, the acyl radical was detected. 1,3-Diphenyl-2-propanone decarbonylated to yield the benzyl radical. Finally, valerophenone yielded the radicals expected by γ-hydrogen abstraction. In a dark reaction, dimethyl sulfoxide reacts with NaOH to generate methyl radicals. The latter result suggests the need for caution in the use of dimethyl sulfoxide with 2-methyl-2-nitrosopropane for the detection of hydroxyl radicals.

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Section: IImentioning

confidence: 99%

Spin-trapping with 2-methyl-2-nitrosopropane: photochemistry of carbonyl-containing compounds. Methyl radical formation from dimethyl sulfoxide

Rosenthal¹,

Mossoba²,

Riesz³

1982

Can. J. Chem.

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“…NO adds slowly to double bonds [55,56], but it reacts very fast with some radicals, such as O 2 ·− [57], carbon-centered radicals [58,59], peroxyl radicals [60] and oxygen [61]. Thus, the decrease in nitrite yield when samples contain either JQ or NQ could be ascribed to the consumption of NO by reacting with peroxyl and/or carbon-centered radicals derived from the pyrolysis of these hydrophobic quinones at the cavitation bubble.…”

Section: Discussionmentioning

confidence: 99%

Quinone-enhanced sonochemical production of nitric oxide from s-nitrosoglutathione

Alegrı́a

Dejesús-Andino

Sanchez-Cruz

2009

Ultrasonics Sonochemistry

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Sonolysis at 75 kHz of argon-and air-saturated aqueous solutions at pH 7.4 containing snitrosogluthathione (GSNO) enhances the production rate of nitric oxide (NO). The quinones, anthraquinone-2-sulfonate (AQ2S) and anthraquinone-2,7-disulfonate (AQ27S) further enhance the NO production over that produced in quinone-depleted sonicated solutions. In contrast, the hydrophobic quinones juglone (JQ) and 1,4-naphthoquinone (NQ) inhibit ultrasound-induced NO detection as compared to quinone-depleted solutions. Larger sonolytical decomposition of the hydrophobic quinones NQ and JQ, as compared to AQ2S and AQ27S, is detected which correlates with a larger production of pyrolysis-derived carbon-centered radicals. Reaction of those radicals with NO could explain NQ and JQ inhibition. This work suggests that sulfonated quinones could be used to enhance NO release from GSNO in tissues undergoing ultrasound irradiation.

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“…The most conspicuous change is the appearance of signals pointing to the presence of a new nitroxide with a N around 8 Gauss. We have attributed this to an acylnitroxide (9), formed by addition of acyl radicals to the nitrosation product 2-nitroso-2-phenyl-propane ("nitrosocumene"). Acyl radicals arise in turn by β-fission of s-butoxy and /z-butoxy radicals generated in nitrite-photolysis.…”

Section: Photochemical and Thermal Generation Ofacylnitroxidesmentioning

confidence: 99%

Spin-trapping in early and some recent nitroso chemistry

Boer¹

1982

Can. J. Chem.

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The radical scavenging properties of nitroso compounds were discovered accidentally during investigations of photochemical nitrosation of hydrocarbons with alkyl nitrites. Depending on the nature of substrates and nitrosating agent, various nitroxides can be generated. Identification of these nitroxides by their esr spectra has triggered the development of the spin-trapping technique which has been useful in the elucidation of many organic radical reaction mechanisms. Recent studies have shown that the behavior of nitrosocyclopropanes and α-chloro-nitroso alkanes is unorthodox upon irradiation. Dark reactions of α-chloro-nitroso alkanes with Grignard reagents lead to nitrones by a polar mechanism and to oximes by electron transfer. In the latter case high yields of hydrocarbon dimers are sometimes obtained from the Grignard and other organometallic reagents, despite the presence of nitroso compounds. In the postulated reaction mechanism dimers and higher associates from the organometallic reagent play an essential role.

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C-nitroso compounds—VI

Cited by 117 publications

References 13 publications

Spin-trapping with 2-methyl-2-nitrosopropane: photochemistry of carbonyl-containing compounds. Methyl radical formation from dimethyl sulfoxide

Spin-trapping with 2-methyl-2-nitrosopropane: photochemistry of carbonyl-containing compounds. Methyl radical formation from dimethyl sulfoxide

Quinone-enhanced sonochemical production of nitric oxide from s-nitrosoglutathione

Spin-trapping in early and some recent nitroso chemistry

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