Oxidation of hindered aniline to iminocyclohexa-2,4-dienone by copper(II) complex of an N-substituted bis-benzimidazolyl ligand.

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Title: Oxidation of hindered aniline to iminocyclohexa-2,4-dienone by copper(II) complex of an N-substituted bis-benzimidazolyl ligand.
Authors: Yadav, Anjana1, Mathur, Pavan1 pavanmat@yahoo.co.in
Source: Inorganica Chimica Acta. Mar2015, Vol. 427, p62-71. 10p.
Subjects: Aniline, Cyclohexadienones, Copper compounds, Metal complexes, Substitution reactions, Benzimidazoles, Ligands (Chemistry)
Abstract: Copper(II) complex of an N-octylated bis-benzimidazolyl ligand is synthesized and characterized. X-ray diffraction study revealed that copper(II) is in a distorted square-planar environment of two benzimidazolyl imine nitrogens and two nitrato ligands. This complex carries out the oxidation of 2,4,6-tri-tert-butylaniline at room temperature utilizing low amounts of tert-butylhydroperoxide (TBHP) as an alternate source of oxygen. 3,5-Di-tert-butyl-6-iminocyclohexa-2,4-dienone is found to be the major product along with 3,5-di-tert-butylcyclohexa-3,5-diene-1,2-dione. The oxidation products have been isolated and characterized by 1 H NMR, 13 C NMR and COSY experiments. The catalytic oxidation proceeds via a copper(II)/copper(III) cycle. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
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Abstract:Copper(II) complex of an N-octylated bis-benzimidazolyl ligand is synthesized and characterized. X-ray diffraction study revealed that copper(II) is in a distorted square-planar environment of two benzimidazolyl imine nitrogens and two nitrato ligands. This complex carries out the oxidation of 2,4,6-tri-tert-butylaniline at room temperature utilizing low amounts of tert-butylhydroperoxide (TBHP) as an alternate source of oxygen. 3,5-Di-tert-butyl-6-iminocyclohexa-2,4-dienone is found to be the major product along with 3,5-di-tert-butylcyclohexa-3,5-diene-1,2-dione. The oxidation products have been isolated and characterized by 1 H NMR, 13 C NMR and COSY experiments. The catalytic oxidation proceeds via a copper(II)/copper(III) cycle. [ABSTRACT FROM AUTHOR]
ISSN:00201693
DOI:10.1016/j.ica.2014.11.025