Oxidative decarboxylation of vicinal dicarboxylic acids as promoted by cuprous oxide in quinoline

Snow, Robert A.; Degenhardt, Charles R.; Paquette, Leo A.

doi:10.1016/0040-4039(76)80139-6

Cited by 40 publications

(30 citation statements)

References 17 publications

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“…This is not surprising as their decarboxylation is known to proceed via a different mechanism involving redox processes. [11] The mechanism of the uncatalyzed thermal decarboxylation of benzoic and substituted benzoic acids was the matter of a series of theoretical investigations starting in the late 1980s. [12] Very recently, BelBruno et al reinvestigated and resummarized these results.…”

mentioning

confidence: 99%

Copper‐Catalyzed Protodecarboxylation of Aromatic Carboxylic Acids

Gooßen¹,

Thiel²,

Rodríguez³

et al. 2007

Adv Synth Catal

209

147

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confidence: 99%

Copper‐Catalyzed Protodecarboxylation of Aromatic Carboxylic Acids

Gooßen¹,

Thiel²,

Rodríguez³

et al. 2007

Adv Synth Catal

209

147

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“…While highly activated carboxylic acids (e.g. perfluorinated benzoic acids) readily decarboxylate without any catalyst, 58 the removal of the carboxylate groups from simple aromatic acids is much more complicated and often requires harsh reaction conditions, an inadequate use of copper or even more expensive silver salts as well as large amounts of additives. 59 In the present work we show that nanoscale copper(I)oxide (Cu 2 O-NPs) embedded in ionic liquids is an active and recyclable catalyst for this reaction.…”

mentioning

confidence: 99%

Recyclable nanoscale copper(i) catalysts in ionic liquid media for selective decarboxylative C–C bond cleavage

Kessler

Gedig

Sahler

et al. 2013

Catal. Sci. Technol.

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Here we report the synthesis and application of finely divided Cu 2 O nanoparticles (Cu 2 O-NPs) in the range from 5.5 nm to 8.0 nm in phosphonium ionic liquids as the first recyclable and effective catalytic system for smooth, ligand-and additive-free protodecarboxylation of 2-nitrobenzoic acid as a model substrate and further derivatives. The reactions run with low catalyst loadings and result in quantitative yield in ten consecutive recycling experiments. In addition this system is highly selective towards electron-poor 2-nitrobenzoic acids.

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“…Several procedures for the syntheses of this compound were tried; the method eventually chosen was the cuprous ion promoted oxidative bis-decarboxylation of 2-methylbicyclo[ 1.2.2lheptane-2,3-dicarboxylic acid (9,10).…”

Section: Resultsmentioning

confidence: 99%

“…The relationship of the benzylic hydrogen and the hydrogen adjacent to the methoxy group, CH--OCH3, will be axial-axial in the trans adduct and axial-equatorial in the cis adduct. Vicinal hydrogen axial-axial coupling (8)(9)(10)(11)(12)(13) is significantly larger than axial-equatorial coupling (2)(3)(4)(5)(6) and the configuration of substituted cyclohexanes can be assigned using this criterion. For the isomer assigned the cis configuration (13-c), the I vicinal couplings of the benzylic hydrogen at 2.70 ppm are 12.9, I 3.5, and 2.9 Hz, corresponding to one axial-axial and two axial-equatorial couplings.…”

Section: Structural Assignmentsmentioning

confidence: 99%

“…2-Methylnorborrz-2-ene (12) The 2-methylnorborn-2-ene was prepared by oxidative bisdecarboxylation of 2-methylbicyclo[2.2.l]heptane-2,3-dicarboxylic acid using a procedure developed by Paquette and co-workers (10). To a 250-mL round bottom flask, equipped for distillation with a receiver in Dry Ice and under a nitrogen atmosphere, was added 9.9 g (0.05 mol) For personal use only.…”

Section: -Methylbicyclo[22 Ilheptane-23-dicarboxylic Acidmentioning

confidence: 99%

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The photochemical nucleophile–olefin combination, aromatic substitution reaction (Part 2): methanol – cyclic olefins, 1,4-dicyanobenzene

Arnold¹,

Snow²

1988

Can. J. Chem.

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Direct irradiation of acetonitrile-methanol (3:l) solutions of 1,4-dicyanobenzene and the cyclic olefins, cyclohexene, 1-methylcyclohexene, norbornene, and 2-methylnorbornene, leads to formation of regio-and stereoisomers of the 1:l:l (alcohol:olefin:aromatic) adducts. This reaction can be photosensitized by electron transfer; addition of electron donors, biphenyl or phenanthrene, to the irradiation mixture generally increases the efficiency and yield of adduct formation. The efficiency of the reaction and the ratio of isomeric adducts are also affected by the addition of salts, particularly magnesium perchlorate. All of the possible regio-and stereoisomers from cyclohexene and I -methylcyclohexene have been identified, two from cyclohexene and four from 1-methylcyclohexene. Three of the four possible isomers from norbornene were characterized; the endo,endo isomer was not detected. There are eight possible isomers from 2-methylnorbornene; six were detected and five have been isolated and identified. The two sterically hindered isomers, those having both the 4-cyanophenyl and the methoxy groups in the endo position, and exo-3-(4-cyanophenyl)-endo-2-methoxy-exo-2-methylnorbornane, were not characterized. The structures of the products were established largely on the basis of the 'H and I3C nuclear magnetic resonance spectra. The mechanism of the reaction is discussed, with emphasis on those factors that may affect the product ratio. The most striking observation is that the reaction is regioselective when magnesium perchlorate is added to the irradiation mixture.

show abstract

Oxidative decarboxylation of vicinal dicarboxylic acids as promoted by cuprous oxide in quinoline

Cited by 40 publications

References 17 publications

Copper‐Catalyzed Protodecarboxylation of Aromatic Carboxylic Acids

Copper‐Catalyzed Protodecarboxylation of Aromatic Carboxylic Acids

Recyclable nanoscale copper(i) catalysts in ionic liquid media for selective decarboxylative C–C bond cleavage

The photochemical nucleophile–olefin combination, aromatic substitution reaction (Part 2): methanol – cyclic olefins, 1,4-dicyanobenzene

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