Notes - The Reduction of Nitrobenzene to Azoxybenzene by Sodium Borohydride

Weill, C. Edwin; Panson, Gilbert S.

doi:10.1021/jo01113a606

Cited by 15 publications

(6 citation statements)

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“…Since no close precedent for the mechanism of reaction (1) is known to us, we have sought further evidence from a labelling experiment, using 2,4-dinitroanisole as substrate. On labelling the 3-position with deuterium, reaction of the substrate with ordinary sodium borohydride should, according to this mechanism, result in the production of 4-nitroanisole containing some deuterium in the 2-position.…”

Section: No* ( 6 )mentioning

confidence: 99%

Sodium borohydride as a reagent for nucleophilic aromatic substitution by hydrogen: the role of hydride Meisenheimer adducts as reaction intermediates

Gold¹,

Miri²,

Robinson³

1980

J. Chem. Soc., Perkin Trans. 2

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Section: No* ( 6 )mentioning

confidence: 99%

Sodium borohydride as a reagent for nucleophilic aromatic substitution by hydrogen: the role of hydride Meisenheimer adducts as reaction intermediates

Gold¹,

Miri²,

Robinson³

1980

J. Chem. Soc., Perkin Trans. 2

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“…Juli 1962) 1-Chlor-2.4-dinitro-benzol laBt sich mit Natriumborhydrid zu l-Chlor-2.4dinitro-cyclohexen- (6) reduzieren. Analog reagieren andere 1 -subst.…”

Section: Umsetzung Von Nitroaromaten Mit Natriumborhydrid Ii1)unclassified

“…Bei der Umsetzung von 1 -Chlor-2.4-dinitro-benzol (I) mit Natriumborhydrid entsteht rasch eine nicht isolierte, tief blaue Verbindung der vermutlichen Struktur II oder 111, die in polaren Losungsmitteln mit uberschiissigem Natriumborhydrid innerhalb einiger Minuten zum farblosen Salz IV weiterreagiert; Weinsaure setzt aus IV l-Chlor-2.4-dinitro-cyclohexen- (6) …”

Section: Umsetzung Von Nitroaromaten Mit Natriumborhydrid Ii1)unclassified

Umsetzung von Nitroaromaten mit Natriumborhydrid, II

Severin

Adam

1963

Chem. Ber.

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“…In 1956, Weill and Panson obtained azoxybenzene from the reduction of nitrobenzene by sodium borohydride in diglyme [ 1 ]. Since then, a few investigations on the reduction of nitroarenes by borohydrides were reported [ 2 , 3 , 4 , 5 , 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water

Liu

Guo

et al. 2011

Molecules

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The synthesis of the azoxybenzenes by the reduction of nitroarenes with reducing agent potassium borohydride in water was reported for the first time. PEG-400 was used as a phase transfer catalyst and could effectively catalyze the reduction. The electronic effects of substituent groups play an important role in determining the reduction efficiencies. Electron-withdrawing substituents promote the formation of the azoxybenzene products, while electron-releasing groups retard the reductions to various degrees depending on the extent of their electron-donating ability.

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Notes - The Reduction of Nitrobenzene to Azoxybenzene by Sodium Borohydride

Cited by 15 publications

References 0 publications

Sodium borohydride as a reagent for nucleophilic aromatic substitution by hydrogen: the role of hydride Meisenheimer adducts as reaction intermediates

Sodium borohydride as a reagent for nucleophilic aromatic substitution by hydrogen: the role of hydride Meisenheimer adducts as reaction intermediates

Umsetzung von Nitroaromaten mit Natriumborhydrid, II

Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water

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