The Furoxans

Kauman, J. V. R.; Picard, J. P.

doi:10.1021/cr50027a002

Cited by 40 publications

(5 citation statements)

References 69 publications

(130 reference statements)

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“…Furoxans are the N-oxide of furazan and are important biological moieties. 87 Alternatively, C 2 H 3 N 2 O 3 + may be visualized as having an NQN bond instead of two CQN bonds, and there is not sufficient information to discriminate between these different structures. The formation of furoxan-like derivatives is consistent with all of the observations derived from HR-MS and HR-MS n .…”

Section: Ms N Characterization Of Degraded Compounds and Photoproductsmentioning

confidence: 99%

Direct aqueous photochemistry of isoprene high-NOx secondary organic aerosol

Nguyen

Laskin

et al. 2012

Phys. Chem. Chem. Phys.

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Secondary organic aerosol (SOA) generated from the high-NO(x) photooxidation of isoprene was dissolved in water and irradiated with λ > 290 nm radiation to simulate direct photolytic processing of organics in atmospheric water droplets. High-resolution mass spectrometry was used to characterize the composition at four time intervals (0, 1, 2, and 4 h). Photolysis resulted in the decomposition of high molecular weight (MW) oligomers, reducing the average length of organics by 2 carbon units. The average molecular composition changed significantly after irradiation (C(12)H(19)O(9)N(0.08) + hν → C(10)H(16)O(8)N(0.40)). Approximately 65% by count of SOA molecules decomposed during photolysis, accompanied by the formation of new products. An average of 30% of the organic mass was modified after 4 h of direct photolysis. In contrast, only a small fraction of the mass (<2%), belonging primarily to organic nitrates, decomposed in the absence of irradiation by hydrolysis. Furthermore, the concentration of aromatic compounds increased significantly during photolysis. Approximately 10% (lower limit) of photodegraded compounds and 50% (upper limit) of the photoproducts contain nitrogen. Organic nitrates and multifunctional oligomers were identified as compounds degraded by photolysis. Low-MW 0N (compounds with 0 nitrogen atoms in their structure) and 2N compounds were the dominant photoproducts. Fragmentation experiments using tandem mass spectrometry (MS(n), n = 2-3) indicate that the 2N products are likely heterocyclic/aromatic and are tentatively identified as furoxans. Although the exact mechanism is unclear, these 2N heterocyclic compounds are produced by reactions between photochemically-formed aqueous NO(x) species and SOA organics.

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Section: Ms N Characterization Of Degraded Compounds and Photoproductsmentioning

confidence: 99%

Direct aqueous photochemistry of isoprene high-NOx secondary organic aerosol

Nguyen

Laskin

et al. 2012

Phys. Chem. Chem. Phys.

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“…The chemistry of the furoxan ring system has been studied extensively, and there are a number of detailed review articles in which the historical development of the structural evidence is presented, 38,[46][47][48] and spectroscopic and crystallographic data are discussed. 48 The ring opening eqn.…”

Section: ð1þmentioning

confidence: 99%

Dinitroso and polynitroso compounds

Gowenlock

Richter‐Addo

2005

Chem. Soc. Rev.

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The growing interest in the chemistry of C-nitroso compounds (RN=O; R = alkyl or aryl group) is due in part to the recognition of their participation in various metabolic processes of nitrogen-containing compounds. C-Nitroso compounds have a rich organic chemistry in their own right, displaying interesting intra- and intermolecular dimerization processes and addition reactions with unsaturated compounds. In addition, they have a fascinating coordination chemistry. While most of the attention has been directed towards C-nitroso compounds containing a single -NO moiety, there is an emerging area of research dealing with dinitroso and polynitroso compounds. In this critical review, we present and discuss the synthetic routes and properties of these relatively unexplored dinitroso and polynitroso compounds, and suggest areas of further development involving these compounds. (126 references.).

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“…Die Konstitution dieser Substanzen, wie diejenige anderer Furoxane war unsicher, bis Calleri et al [4] 1967 durch Rontgen-Analyse bewiesen, dass Aryl-alkyl-furoxane die Struktur 3 und 4 besitzen. Damit wurden die Konstitutionsvorschlage 5-10, die seit der Herstellung des ersten Furoxans durch Kekde' [5] im Jahre 1858 imnier wieder in der Literatur [6] [7] auftauchten, widerlegt. In der Tat ermoglicht die schrittweise Durchfuhrung der Synthese die Isolierung von 4-Phenyl-furoxan (13) und von amphi-Phenyl-aminoglyoxim (15) [8].…”

Section: Aminofuroxane 1 Synthese Und Strukturl) Von Andre R Gagneuunclassified

Aminofuroxane. 1. Synthese und Struktur

Gagneux¹,

Meier²

1970

Helvetica Chimica Acta

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1883these reflections, though weak, are present. The contributions of the two arsenic atoms to the hkO reflections cancel one another at present and the carbon atoms only contributy because they have different y co-ordinates. We suspect that the y (and possibly also the z) co-ordinates of the two arsenic atoms are not identical as shown in Table 3, but these two atoms could not be resolved in the OkZ projection.We thank Prof. A . L . Rheingold who suggested the problem and kindly supplied the crystals.Summary. Phenylglyoximes are transformed in a single operation into 3-amino-4-phenylfuroxans which rearrange quantitatively to their 3-phenyl-4-amino-isomers above 80". A mechanism for the synthesis is proposed and supported by the isolation of intermediates. Proof for the structure of both furoxan isomers and intermediate phenylaminoglyoximes rests on chemical transformations, mechanistic considerations, and the influence of certain structural changes on the UV.spectra.

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The Furoxans

Cited by 40 publications

References 69 publications

Direct aqueous photochemistry of isoprene high-NOx secondary organic aerosol

Direct aqueous photochemistry of isoprene high-NOx secondary organic aerosol

Dinitroso and polynitroso compounds

Aminofuroxane. 1. Synthese und Struktur

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