Nucleophilic reactions of quinones

Kutyrev, A. A.; Москва, В. В.

doi:10.1070/rc1991v060n01abeh001032

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Enzymatic Oxidation1

Scheme 111

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1998

2024

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Cited by 80 publications

(43 citation statements)

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“…The quinone is then reduced back to its original catechol. As electrophiles, they can also react with nucleophiles like amino derivatives (Kutyrev & Moskva, 1991).…”

Section: Enzymatic Oxidationmentioning

confidence: 99%

Oxidation mechanisms occurring in wines

Oliveira

Ferreira

Freitas

et al. 2011

Food Research International

319

254

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“…The quinone is then reduced back to its original catechol. As electrophiles, they can also react with nucleophiles like amino derivatives (Kutyrev & Moskva, 1991).…”

Section: Enzymatic Oxidationmentioning

confidence: 99%

Oxidation mechanisms occurring in wines

Oliveira

Ferreira

Freitas

et al. 2011

Food Research International

319

254

View full text Add to dashboard Cite

“…This fact indicates that the pink compound is produced not by air oxidation of the reaction product of 1,2-benzoquinone and aniline, but by the reaction of 1,2-benzoquinone and aniline. It has been pointed out that a new compound is formed by substituting the hydrogen atom of the 4-position in quinone with an amino group by nucleophilic reaction [4,5] when amine is reacted with benzoquinone. However, the pink color compound should not be produced by substitution, because the quinone ring of the new compound is reduced to colorless benzene ring if hydrogen is released from the quinone ring.…”

mentioning

confidence: 99%

Formation of Aniline-Bonded Catechols in Aqueous Solution and Their Electrochemical Behavior at a Carbon Felt Electrode

et al. 1998

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The oxidized form of catechol (1,2-benzoquinone) reacts with aniline at neutral pH range and the electroactive 1:1 and 1:2 compounds of catechol and aniline which exhibit separative reversible redox waves are produced and their formal electrode potentials are ¹0.05 V and ¹0.23 V, respectively. The 1:1 compound is considered to be an adduct with pink color and the 1:2 compound is considered to be two anilines substituted catechol from the MS data of molecular weight (290) and 1 H and 13 C NMR data. The 1:2 compound accumulates on the carbon electrode surface due to its affinity to the carbon felt electrode and a detection limit of this compound was found to be 5 × 10 ¹9 M.

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“…28 Interestingly, this reaction is possible even for phenols that first produce in situ the corresponding o quinones. This approach involving Cu 2+ complexes with secondary amine has been successfully employed for the synthesis of such dialkylamino o quinones which are quinoline, indole, acridine, isoquinoline, quinoxaline, benzofuran, and benzothiazole derivatives (Scheme 13) (see Refs 28,29).…”

Section: Scheme 11mentioning

confidence: 99%