II. Ueber das Dinitrosonaphtalin

Ilinski, M.

doi:10.1002/cber.18860190184

Cited by 10 publications

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“…The use of stannous chloride as the reducing agent differs in that although reduction in general stops at the production of the furazan (18,35,173,202), as exemplified by methyl (methoxyphenyl)furoxan, bis(phenyl)furoxan, furoxan dialdoxime, and dibenzoylfuroxan, it can extend to the formation of the amine or the diamide as in the case of naphthoquinone dioxime (90,237). Some reactions involving the use of stannous chloride have not been explained (4), while the others, especially those in which long side chains are present on the furoxan nu- cleus, exhibit a complicated series of reactions in which reduction of the furazan to the glyazine and lactone formation on the side chain can occur.…”

Section: Arcochsmentioning

confidence: 99%

“…The behavior of furoxans on reduction by hydroxylamine (68, 158, 177, 237), hydrazine (57), hydrogen, ammonium sulfide, phosphorus sulfides (4, 90,192), sulfur dioxide and thionyl chloride (33,226), phosphorus and sodium (18, 189), phosphorus pentachloride (4, 142, 235), and hydrogen iodide (18, 62) is much like that described for zinc and stannous chloride in that the specific furoxans plus the specific conditions will determine whether a reaction occurs or whether the product is a furazan, an amine, a dioxime, or a decomposition product. Although a definitive study has yet to be made, reduction by zinc or hydroxylamine will, in general, result in the formation of dioximes and not furazans, while reductions by the other agents described will result in furazans and not dioximes.…”

Section: Arcochsmentioning

confidence: 99%

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The Furoxans

Kauman¹,

Picard²

1959

Chem. Rev.

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456but the following year he considered that his products were oximino compounds (180,181). Historically, Koreff (100) is credited with the preparation of the same substance by the oxidation of a dioxime, although Koreff acknowledged that H. Schmid described the compound to him and Ilinski (90) reported its preparation in the same year. Although no name was proposed for their compounds, they did suggest that the oxidation product of /3-naphthoquinone dioxime, CioH6(=NOH)2, had the same properties as the substance obtained by oxidizing phenylglyoxime and that the compound was not a dinitroso compound but of the type later to be called glyoxime peroxide (11). At very nearly the same time that Holleman (84) proposed the name "dinitrosoacyl" for the product that he obtained by nitrating acetophenone, Beckmann (28) proposed that his product from the nitration of benzil dioxime be called azodibenzenyl hyper oxide, and Scholl (187) gave the name "benzildioxime super oxide" to the product that he obtained from benzaldoxime.Angelí (11) then repeated the work of Tonnies and Beckmann and suggested the name "glyoxime peroxide." All of these authors were referring to the same structure in an aliphatic series of compounds, viz.:

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Section: Arcochsmentioning

confidence: 99%

Section: Arcochsmentioning

confidence: 99%

The Furoxans

Kauman¹,

Picard²

1959

Chem. Rev.

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Furazans: Ring Index 84

Behr¹

1962

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Dinitrogen Trioxide-Mediated Domino Process for the Regioselective Construction of 4-Nitrofuroxans from Acrylic Acids

et al. 2014

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4-Nitrofuroxans(4-nitro-1,2,5oxadiazole 2-oxides) were prepared by a dinitrogen trioxide-mediated domino reaction of acrylic acids under the action of NaNO 2 excess in AcOH at room temperature. The reaction proceeds completely regioselectively and presents a new, simple, general, and safe method for the preparation of both 3-aryl-and 3-alkyl-4-nitrofuroxans available with difficulty before. A mechanism for the furoxan ring construction through a four-step one-pot protocol is proposed. The synthesized nitrofuroxans have been characterized by multinuclear NMR spectroscopy and X-ray powder diffraction. C 2014 Wiley Periodicals, Inc. Heteroatom Chem. 25:226-237, 2014; View this article online at wileyonlinelibrary.com.

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II. Ueber das Dinitrosonaphtalin

Cited by 10 publications

References 0 publications

The Furoxans

The Furoxans

Furazans: Ring Index 84

Dinitrogen Trioxide-Mediated Domino Process for the Regioselective Construction of 4-Nitrofuroxans from Acrylic Acids

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