Reactions of ortho-aminophenols and ortho-aminothiophenols with 1,3,5-trinitrobenzene

Дутов, М. Д.; Vorob'ev, Sergei S.; Serushkina, O. V.; Шевелев, С. А.; Уграк, Б. И.; Качала, В. В.

doi:10.1070/mc2006v016n04abeh002257

Cited by 7 publications

(1 citation statement)

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“…This reaction is thought to involve nitro group displacement to yield intermediates (4), which undergo oxidative substitution of hydrogen by the amino group. 18 The corresponding reaction of TNB with o-aminothiophenols yields 1,3-dinitrophenothiazine derivatives.…”

Section: The S N Ar Mechanismmentioning

confidence: 99%

Nucleophilic Aromatic Substitution

Crampton

2010

Organic Reaction Mechanisms · 2006

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There has been a study of the dediazoniation of 4-nitrobenzenediazonium ions in methanol-water mixtures under acidic conditions using kinetic, spectrophotometric, and chromatographic methods. Two decomposition routes were identified: an ionic pathway yielding nitrophenol and nitroanisole, and a radical pathway involving transient diazo ethers which undergo homolytic fragmentation giving nitrobenzene or 4,4 -dinitrobiphenyl. 1 Catalysis by the Cu(I)-Cu(II)-1,10-phenanthroline system has been reported in the reaction of arenediazonium salts with potassium thiocyanate to yield aryl thiocyanates. 2 Bis(trifluoromethanesulfonyl)amide anions (Tf 2 N − ) are usually considered to have very low nucleophilic reactivity. However, in imidazolium ionic liquids this anion has been shown to have higher reactivity than bromide ions in heterolytic dediazoniation reactions. 3 It has been shown that displacement of the iodo substituent in 4-iodo-1,1,2,2,9,9,10, 10-octafluoro[2.2]paracyclophane by arenethiolates or by stabilized enolates occurs by the radical chain S RN 1 mechanism. The reaction occurs in DMF with photochemical stimulation. 4 The S N Ar MechanismThere has been a review of relationships between activation parameters and mechanisms for biomolecular reactions in solution, including both nucleophilic substitutions and additions. 5 Several studies have been reported involving substitutions by amine nucleophiles where both electronic and steric effects may be important. Kinetic studies of the reactions of 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether (1) with ring-substituted 175

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Section: The S N Ar Mechanismmentioning

confidence: 99%

Nucleophilic Aromatic Substitution

Crampton

2010

Organic Reaction Mechanisms · 2006

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Intramolecular S _N Ar Reactions

Terrier

2013

Modern Nucleophilic Aromatic Substitution

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