The electrochemical synthesis and structure determination of 3,3',5,5'-tetra-tert-butyl-1,1'-biphenylidene-4,4'-quinone

Khan, M. A.; Osman, Akhtar; Tuck, Dennis G.

doi:10.1107/s0108270186092120

Cited by 9 publications

(11 citation statements)

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“…In previous report, TTBDQ was synthesized by electrochemical anodic oxidation of compound 2 in the presence of metals, such as Zn, Cd, or Hg. 18 Herein, TTDBQ was generated by electrochemical oxidation of 2 in the absence of metal ions. TTBDQ and its X-ray crystal structure prepared by the chemical oxidation of 2 have also been reported.…”

Section: Resultsmentioning

confidence: 99%

“…Phenols were electrochemically oxidized in solution by anodic oxidation in the presence of metals such as Zn, Cd, and Hg. 8 The oxidation products of catechols, dopamine, hydroquinone, and para-substituted phenols such as tyrosine, tyramine, and 4-ethylphenol were mostly o-or p-quinones. 9 Based on the phenoxyl radical intermediate, the oxidation mechanism of phenol involves loss of an electron alongside deprotonation in a radical mechanism.…”

Section: Introductionmentioning

confidence: 99%

“…The electrochemical oxidation of a phenol is initiated at largely positive potentials. Phenols were electrochemically oxidized in solution by anodic oxidation in the presence of metals such as Zn, Cd, and Hg . The oxidation products of catechols, dopamine, hydroquinone, and para -substituted phenols such as tyrosine, tyramine, and 4-ethylphenol were mostly o - or p -quinones …”

Section: Introductionmentioning

confidence: 99%

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Selective Electrochemical versus Chemical Oxidation of Bulky Phenol

et al. 2016

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The electrochemical oxidation of selected tert-butylated phenols 2,6-di-tert-butyl-4-methylphenol (1), 2,6-di-tert-butylphenol (2), 2,4,6-tri-tert-butylphenol (3), 2-tert-butylphenol (4), and 4-tert-butylphenol (5) was studied in an aprotic environment using cyclic voltammetry, square-wave voltammetry, and UV-vis spectroscopy. All compounds exhibited irreversible oxidation of the corresponding phenol or phenolate ion. Compound 2 was selectively electrochemically oxidized, while other phenol analogues underwent mostly chemical oxidation. The electrochemical oxidation of 2 produced a highly absorbing product, 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone, which was characterized by X-ray crystal diffraction. The electrochemical oxidation was monitored as a function of electrochemical parameters and concentration. Experimental and theoretical data indicated that the steric hindrance, phenoxyl radical stability, and hydrogen bonding influenced the outcome of the electrochemical oxidation. The absence of the substituent at the para position and the presence of the bulky substituents at ortho positions were structural and electrostatic requirements for the selective electrochemical oxidation.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Selective Electrochemical versus Chemical Oxidation of Bulky Phenol

et al. 2016

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“…A similar process happened when an acetonirile/benzene or methanol/benzene solution of 2,6-bis-tertbutyl-phenol was electrolyzed with a Zn, Cd or Hg anode under a nitrogen atmosphere [343]. Useful crystals for X-ray diffraction studies could be obtained but the compound was confirmed to be 3,3'-5,5'-tetra-tertbutyl-1,1'-biphenylidene-4,4'quinone ( Fig.…”

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confidence: 92%

“…13. Molecular structures of [Cu(HL106) 2 (DMSO)] [43], left, and, 3,3'-5,5'-tetratertbutyl-1,1'-biphenylidene-4,4'-quinone [343], right.…”

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confidence: 99%