Aromatic substitution. 45. Transfer nitration of aromatics with N-nitropyridinium and quinolinium ions

Oláh, George A.; Narang, Subhash C.; Oláh, Judith A.; Pearson, Ronald L.; Cupas, Chris A.

doi:10.1021/ja00530a033

Cited by 42 publications

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“…For the role of the nitropyridine nucleus in the development of medicinal agents and in the field of agrochemicals, see: Davis et al (1996). For the properties and use of pyridine derivatives, see: Vacher et al (1998); Olah et al (1980); Bare et al (1989). For standard bond lengths, see: Allen et al (1987).…”

Section: Related Literaturementioning

confidence: 99%

2,6-Dichloro-3-nitropyridine

et al. 2011

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The asymmetric unit of the title compound, C5H2Cl2N2O2, consists of two crystallographically independent molecules. The pyridine ring in each molecule is essentially planar, with maximum deviations of 0.004 (4) and 0.007 (4) Å. Short Cl⋯O [3.09 (3) and 3.13 (4) Å] and Cl⋯Cl [3.38 (12) Å] contacts were observed. No significant intermolecular interactions were observed in the crystal packing.

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Section: Related Literaturementioning

confidence: 99%

2,6-Dichloro-3-nitropyridine

et al. 2011

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“…There are many useful reagents for nitration such as concentrated nitric acid,6 mixtures of nitric acid with sulfuric acid,7 nitric acid in acetic anhydride,8 nitrate salts in trifluoroacetic anhydride,9 ozone and nitrogen dioxide,10 N 2 O 5 and Fe(acac) 3, 11 N‐nitropyridinium and quinolinium salts,12 nitric acid and trifluoromethanesulfonic acid13 or trifluoromethanesulfonic anhydride,14 metal nitrates in sulfuric acid,15–17 lanthanide(III) nosylates,18 guanidinium nitrate,19 potassium nitrate or nitric acid and boron trifluoride monohydrate mixtures,20 and sodium nitrate/chlorotrimethyl silane and aluminium chloride mixtures 21. Many of these reactions have been carried out in the presence of protic or Lewis acids.…”

Section: Introductionmentioning

confidence: 99%

Regioselective and green synthesis of nitro aromatic compounds using polymer‐supported sodium nitrite/KHSO₄

Zarchi

Rahmani

2011

J of Applied Polymer Sci

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Polymer supported reagents have become the subject of considerable and increasing interest as insoluble materials in the organic synthesis. Use of polymeric reagents simplifies routine nitration of aromatic compounds because it eliminates traditional purification. In this article, the use of readily available cross-linked poly(4-vinylpyridine) supported sodium nitrite, [P 4 -Me] NO 2 , as an efficient polymeric nitrating agent in the presence of KHSO 4 is described. A good range of available aromatic compounds were also subjected to nitration in the presence of [P 4 -Me] NO 2 /KHSO 4 . This reagent is regioselective and chemoselective nitrating polymeric reagent for activated aromatic rings. In this procedure, the work-up is easy, and the spent polymeric reagent is easily regenerated and reused.

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“…The same catalyst has also been reported to be effective in solution phase esterification reactions (46). Beltrame, Carniti and Nespoli (47) used Nafion as a catalyst for the isomerization of m-xylene and Olah (48) has used Nafion as a catalyst for Friedel-Craft reactions of toluene and phenol with alkylchloroformâtes and oxalates. The chemical inertness (at least below 220°C) of this heterogeneous catalyst confers obvious advantages over more conventional homogeneous superacid catalysts (43,49).…”

Section: Catalysismentioning

confidence: 96%

General Applications of Perfluorinated Ionomer Membranes

Kipling¹

1982

ACS Symposium Series

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Described here are applications other than industrial chloralkali, water electrolysis and fuel cells. The applications are divided into six general classes. SeparatorsThe use of Nafion as a separator in cells for chloralkali electrolysis is described elsewhere. The exceptional chemical inertness and thermal stability coupled with favourable electrical conductivity being of particular advantage in this application. These properties have been exploited in a number of other electrochemical applications.The RAI Research Corporation also offers a range of battery separators under the name of Permion (1) . These membranes are made by radiation grafting of a suitably active group onto an inert base film. The active groups include weak acids such as acrylic and substituted acrylic acid and stronger acidic groups such as sulfonated styrene. The base film can be Teflon R, polyethylene or polypropylene. They are thus not strictly perfluorinated membranes as is Nafion, but in chemical inertness and in many physical properties such as electrical conductivity and ion flux are useful as separators in batteries.Grot (2, 3, 4) has summarized the properties of some perfluorinated membranes used as separators, mainly for chloralkali electrolysis, and also described regeneration of chromic acid solutions. Solutions of chromium(VI) in sulfuric acid are used in a number of industrial processes. For example in etching plastics prior to metallizing. The used solution contains chromium(III) which can be electrolytically reoxidized to chromium(VI) using lead anodes. Nafion in tubular form (80 mm diameter) is used as the separator in cylindrical cells. Sulfuric acid is used as the catholyte, the permselectivity of the Nafion ensuring that little sulfate ion migrates to the chromium(VI) solution. In the regeneration of chrome plating solutions even small amounts of sulfate migrating across the separator would upset the critical ratio 0097-6156/82/0180-0475$05.00/0

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Aromatic substitution. 45. Transfer nitration of aromatics with N-nitropyridinium and quinolinium ions

Cited by 42 publications

References 0 publications

2,6-Dichloro-3-nitropyridine

2,6-Dichloro-3-nitropyridine

Regioselective and green synthesis of nitro aromatic compounds using polymer‐supported sodium nitrite/KHSO₄

General Applications of Perfluorinated Ionomer Membranes

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Aromatic substitution. 45. Transfer nitration of aromatics with N-nitropyridinium and quinolinium ions

Cited by 42 publications

References 0 publications

2,6-Dichloro-3-nitropyridine

2,6-Dichloro-3-nitropyridine

Regioselective and green synthesis of nitro aromatic compounds using polymer‐supported sodium nitrite/KHSO4

General Applications of Perfluorinated Ionomer Membranes

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Regioselective and green synthesis of nitro aromatic compounds using polymer‐supported sodium nitrite/KHSO₄