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Aerobic oxidation of 2,4,6-tri-tert-butylphenol to quinones catalyzed by copper(II) complexes of an N-octylated bis-benzimidazolyl ligand.

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Title: Aerobic oxidation of 2,4,6-tri-tert-butylphenol to quinones catalyzed by copper(II) complexes of an N-octylated bis-benzimidazolyl ligand.
Authors: Yadav, Anjana1, Mathur, Pavan1 pavanmat@yahoo.co.in
Source: Inorganica Chimica Acta. Aug2015, Vol. 435, p206-214. 9p.
Subjects: Oxidation of phenol, Quinone, Copper compounds, Complex compounds synthesis, Benzimidazoles, Dealkylation
Abstract: Copper(II) complexes of a N-octylated bisbenzimidazolyl ligand are synthesized and characterized. These complexes carry out the oxidative dealkylation of 2,4,6-tri-tertbutylphenol (TTBP) using molecular oxygen to 2,6-ditertbutylbenzoquinone and 4,6-di-tertbutylbenzoquinone. The oxidation proceeds via a phenoxyl radical species detected spectrophotometrically, and by EPR. A reactive copper(II)-dioxygen species is involved that carries out the oxidation reaction. A comparison of the rates of formation of the 4,6-di-tert-butylbenzoquinone versus 2,6-di-tert-butylbenzoquinone suggests that alternative pathway may exist for the formation of the para-quinone derivative. Isolation of an intermediate 4,4′-peroxybis(2,4,6-tri-tert-butylcyclohexa-2,5-dienone species and its structural characterization supports the above contention. [ABSTRACT FROM AUTHOR]
Copyright of Inorganica Chimica Acta is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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DbLabel: Engineering Source
An: 108785813
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  Data: Aerobic oxidation of 2,4,6-tri-tert-butylphenol to quinones catalyzed by copper(II) complexes of an N-octylated bis-benzimidazolyl ligand.
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  Data: <searchLink fieldCode="AR" term="%22Yadav%2C+Anjana%22">Yadav, Anjana</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Mathur%2C+Pavan%22">Mathur, Pavan</searchLink><relatesTo>1</relatesTo><i> pavanmat@yahoo.co.in</i>
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  Data: <searchLink fieldCode="JN" term="%22Inorganica+Chimica+Acta%22">Inorganica Chimica Acta</searchLink>. Aug2015, Vol. 435, p206-214. 9p.
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  Data: <searchLink fieldCode="DE" term="%22Oxidation+of+phenol%22">Oxidation of phenol</searchLink><br /><searchLink fieldCode="DE" term="%22Quinone%22">Quinone</searchLink><br /><searchLink fieldCode="DE" term="%22Copper+compounds%22">Copper compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Complex+compounds+synthesis%22">Complex compounds synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Benzimidazoles%22">Benzimidazoles</searchLink><br /><searchLink fieldCode="DE" term="%22Dealkylation%22">Dealkylation</searchLink>
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  Data: Copper(II) complexes of a N-octylated bisbenzimidazolyl ligand are synthesized and characterized. These complexes carry out the oxidative dealkylation of 2,4,6-tri-tertbutylphenol (TTBP) using molecular oxygen to 2,6-ditertbutylbenzoquinone and 4,6-di-tertbutylbenzoquinone. The oxidation proceeds via a phenoxyl radical species detected spectrophotometrically, and by EPR. A reactive copper(II)-dioxygen species is involved that carries out the oxidation reaction. A comparison of the rates of formation of the 4,6-di-tert-butylbenzoquinone versus 2,6-di-tert-butylbenzoquinone suggests that alternative pathway may exist for the formation of the para-quinone derivative. Isolation of an intermediate 4,4′-peroxybis(2,4,6-tri-tert-butylcyclohexa-2,5-dienone species and its structural characterization supports the above contention. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Inorganica Chimica Acta is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.ica.2015.06.026
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      – Code: eng
        Text: English
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        PageCount: 9
        StartPage: 206
    Subjects:
      – SubjectFull: Oxidation of phenol
        Type: general
      – SubjectFull: Quinone
        Type: general
      – SubjectFull: Copper compounds
        Type: general
      – SubjectFull: Complex compounds synthesis
        Type: general
      – SubjectFull: Benzimidazoles
        Type: general
      – SubjectFull: Dealkylation
        Type: general
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      – TitleFull: Aerobic oxidation of 2,4,6-tri-tert-butylphenol to quinones catalyzed by copper(II) complexes of an N-octylated bis-benzimidazolyl ligand.
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              Text: Aug2015
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