Oxidation of 4-alkyl-2,6-di-tert-butylphenols with .beta.-manganese dioxide

Dietl, H.; Young, Howard S.

doi:10.1021/jo00975a048

Cited by 10 publications

(3 citation statements)

References 1 publication

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“…(2) The total amount of indoline and indole was nearly equal to the amount of the charged indoline. (3) The total amount of aniline and nitrobenzene was equal to the amount of the charged nitrobenzene. Other products, such as azo and azoxy compounds, were not detected by GLC and TLC analysis.…”

Section: Resultsmentioning

confidence: 99%

“…RhmCl?1 + indoline -Rh!Cl + indole + 2HC1 (3) Rh!Cl + PhN02 -Rh'CKPhNOz) (4) RlPCUPhNOa) + 3 indoline -*• Rh!Cl + PhNH2 + 3 indole + 2H20 (5) According to this suggestion, RhCl3 is activated to a Rh(I) species by indoline (eq 3), nitrobenzene coordinates to the Rh(I) species (eq 4), and then the coordinated nitrobenzene is reduced to aniline by the hydrogen donor (eq 5). As described before, the coordination of nitrobenzenes to RhCl3 was confirmed by the spectroscopic study.…”

Section: Discussion Of Mechanismmentioning

confidence: 99%

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Transfer hydrogenation and transfer hydrogenolysis. 13. Hydrogen transfer from cyclic amines to aromatic nitro compounds catalyzed by noble metal salts

Imai¹,

Nishiguchi²,

Fukuzumi³

1977

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Discussion Of Mechanismmentioning

confidence: 99%

Transfer hydrogenation and transfer hydrogenolysis. 13. Hydrogen transfer from cyclic amines to aromatic nitro compounds catalyzed by noble metal salts

Imai¹,

Nishiguchi²,

Fukuzumi³

1977

J. Org. Chem.

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“…In the first case the fluoride anion attacks the cation-radical 11 (path C) at the ortho and para position, thus forming fluoro-substituted radical intermediate (14) which, after second electron transfer, transforms to the corresponding fluoro carbocationic species (15). At this point the reaction could split in two ways depending on the …”

Section: Methodsmentioning

confidence: 99%

The effect of the reaction conditions on the course of the reactions of hindered phenols with N-F reagents

Stavber¹,

Jereb²,

Zupan³

2002

Arkivoc

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Abstract2,4,6-Trialkyl substituted phenols were selectively transformed in high yield to para-quinols or para-quinol ethers by reaction with the N-fluoro-1,4-diazoniabicyclo[2.2.2]octane salt analogues Selectfluor TM F-TEDA-BF 4 or Accufluor TM NFTh in acetonitrile in the presence of water or alcohols. At low temperature 2,4,6-tri-tert-butylphenol in pure acetonitrile gave 2-fluoro and 4-fluoro substituted cyclohexadienone products with both reagents, while at elevated temperature 2-fluoro-4,6-di-tert-butylphenol was quantitatively formed. The mechanism postulated the SET proccess, thus forming cation-radical intermediates, as the key step of the reaction was proposed.

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Synthese von Styren‐ und Butadien‐Cyclosiloxan‐Blockcopolymeren mit Antioxidansresten

1988

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Oxidation of 4-alkyl-2,6-di-tert-butylphenols with .beta.-manganese dioxide

Cited by 10 publications

References 1 publication

Transfer hydrogenation and transfer hydrogenolysis. 13. Hydrogen transfer from cyclic amines to aromatic nitro compounds catalyzed by noble metal salts

Transfer hydrogenation and transfer hydrogenolysis. 13. Hydrogen transfer from cyclic amines to aromatic nitro compounds catalyzed by noble metal salts

The effect of the reaction conditions on the course of the reactions of hindered phenols with N-F reagents

Synthese von Styren‐ und Butadien‐Cyclosiloxan‐Blockcopolymeren mit Antioxidansresten

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