Review: Coordination Chemistry of o -Quinone Complexes

Kharisov, Boris I.; Méndez‐Rojas, Miguel A.; Гарновский, А. Д.; Ivakhnenko, E. P.; Ortiz-Méndez, Ubaldo

doi:10.1080/0095897022000001511

Cited by 37 publications

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“…The antimony compounds are used as components of catalytic systems and reagents in fine organic and organometallic synthesis [11][12][13][14]. In addition, many organoantimony compounds dem onstrate antimicrobial properties and possess antitu mor activity [15][16][17].The chemistry of coordination compounds of o quinone and related ligands is widely developed to the present time [18][19][20] because of the use of their com plexes as model objects in magnetochemical studies, for the construction of molecular switchers, and as catalytic systems. Sterically hindered di o quinones are presently studied to a less extent, although they represent a promising type of ligands for the design of spatially ordered structures [21][22][23][24][25].…”

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confidence: 99%

Triaryl- and trialkylantimony(V) Bis(catecholates) based on 1,1′-spirobis[3,3-dimethylindanequinone-5,6]: Spectroscopic and electrochemical studies

et al. 2012

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Scientific interest in coordination and organome tallic antimony(V) derivatives is continuously increas ing in the recent two decades [1][2][3][4], which is due to the possibility of using these compounds in diverse areas of fundamental and applied science. These com plexes demonstrate structural variety from monomeric compounds to associated structures and supramolecu lar ensembles [5][6][7][8][9][10]. The antimony compounds are used as components of catalytic systems and reagents in fine organic and organometallic synthesis [11][12][13][14]. In addition, many organoantimony compounds dem onstrate antimicrobial properties and possess antitu mor activity [15][16][17].The chemistry of coordination compounds of o quinone and related ligands is widely developed to the present time [18][19][20] because of the use of their com plexes as model objects in magnetochemical studies, for the construction of molecular switchers, and as catalytic systems. Sterically hindered di o quinones are presently studied to a less extent, although they represent a promising type of ligands for the design of spatially ordered structures [21][22][23][24][25]. The introduction of various binding units (bridging groups) into the di o quinone structure makes it possible to change con siderably the character of mutual effects of the o quinone moieties in the di o quinone molecule and to vary the exchange magnetic interactions between the radical anion semiquinone derivatives from antiferro magnetic to ferromagnetic [22,24].In addition, the most part of studies of the o quinone complexes was carried out with the transi tion metal compounds, whereas the coordination chemistry of nontransition metals with redox active ligands is poorly studied [26]. This is also valid for the antimony o quinone complexes. Among the binuclear antimony complexes (bis(catecholate) derivatives), the derivatives of 4,4' di [(3 methyl 6 tert butyl o benzoquinone) and di o quinones based on 3,6 di tert butyl o benzoquinone containing the ethylene or piperazine bridging groups were described [27][28][29][30].The purpose of the present work is to synthesize antimony(V) bis(catecholate) complexes based on nonsymmetric 1,1' spirobis[3,3 dimethylindane quinone 5,6] (Q Spiro Q) and to study them by IR and NMR spectroscopy and cyclic voltammetry (CV). EXPERIMENTALThe synthesis and study of the properties of the complexes were carried out in evacuated ampules in the absence of oxygen. In all cases, the yields of the target products were higher than 90%. The solvents Triaryl and Trialkylantimony(V) Bis(catecholates) Based on 1,1' Spirobis[3,3 Dimethylindanequinone 5,6]: Abstract-A series of new binuclear bis(catecholate) antimony(V) complexes based on 1,1' spirobis[3,3 dimethylindanequinone 5,6] with various substituents at the central antimony atoms, R 3 Sb(Cat Spiro Cat)SbR 3 (I-IV) and R 3 Sb(Cat Br Spiro Br Cat)SbR 3 (V-VIII) (R = p fluorophenyl, phenyl, p tolyl, and ethyl), were synthesized. Spirobis(catecholates) I-III exhibit two one electron oxidation waves on the cycli...

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confidence: 99%

Triaryl- and trialkylantimony(V) Bis(catecholates) based on 1,1′-spirobis[3,3-dimethylindanequinone-5,6]: Spectroscopic and electrochemical studies

et al. 2012

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“…110 °C. 1 1 one (12). A catalytic amount of TsOH was added to a solution of 3,5 di (tert butyl)pyrocatechol (5) (6.3 g, 0.028 mol) and compound 11 (8 g, 0.034 mol) in benzene (200 mL).…”

Section: Methodsmentioning

confidence: 98%

“…The yield was 4.66 g (38%). 1 2,4,6,8 Tetra(tert butyl) 9 methoxyphenoxazin 1 one (15). Dimethyl sulfate (0.75 mL, 0.006 mol) and an excess of dry K 2 CO 3 were added to a solution of compound 12 (1 g, 0.002 mol) in acetone (20 mL).…”

Section: Methodsmentioning

confidence: 99%

“…The yield was 0.72 g (80%). 1 Crystals of compound 12 were grown by recrystalliza tion from ethanol. At 100 K, the crystals of (C 30 H 45 NO 4 ) 12 are monoclinic, space group P2 1 /n, a = 13.8821(19) Å, b = = 9.1178(13) Å, c = 22.450(3) Å, β = 96.869(3)°, V = 2821.2(7) Å 3 , Z = 4, d calc = 1.139 g cm -3 , μ(MoKα) = 0.74 cm -1 , F(000) = = 1056.…”

Section: Methodsmentioning

confidence: 99%

“…1 The development of methods for the synthesis of steri cally hindered quinoneimine systems 2,3 made it possible to prepare 2,4,6,8 tetra(tert butyl)phenoxazin 1 one (1). [4][5][6] It appeared that the reaction of 3,5 di(tert butyl) 1,2 benzoquinone (2) with 3,5 di(tert butyl) 2 hydroxyaniline 3 gives sterically hindered tricyclic system 1 (see Ref.…”

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Synthesis, chemical properties, and crystal structure of 2,4,6,8-tetra(tert-butyl)-9-hydroxyphenoxazin-1-one

et al. 2009

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The reaction of di(tert butyl) derivatives of pyrocatechol with 2,6 dihydroxyaniline afford ed 2,4,6,8 tetra(tert butyl) 9 hydroxyphenoxazin 1 one. The chemical properties of the reac tion product and its ability to form complexes with metal salts as the tridentate ligand were investigated. The structure of hydroxyphenoxazinone was established by X ray diffraction.Key words: 2,4,6,8 tetra(tert butyl) 9 hydroxyphenoxazin 1 one, tautomerism, metal che lates, tridentate ligands, ESR spectroscopy, X ray diffraction study, quantum chemical cal culations.Phenoxazine systems and their sterically hindered structural analogs can be involved in reversible one elec tron redox reactions to form paramagnetic intermediates, the presence of the tert butyl groups leading to a substan tial increase in the stability of such free radical species. 1

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[3+1+1] Annulation Reaction of Benzo‐1,2‐Quinones, Aldehydes and Hydroxylamine Hydrochloride: Access to Benzoxazoles with Inorganic Nitrogen Source

2021

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A synthesis of benzoxazoles with an inorganic nitrogen source is reported. By employing large‐tonnage industrial feedstock inorganic hydroxylamine hydrochloride as the nitrogen source, its [3+1+1] annulation reaction with benzo‐1,2‐quinones and aldehydes delivers various useful benzoxazoles in high yields. Preliminary mechanistic studies prove that the quinone oxime rather than the aldehyde oxime is the reaction intermediate.

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Review: Coordination Chemistry of o -Quinone Complexes

Cited by 37 publications

References 0 publications

Triaryl- and trialkylantimony(V) Bis(catecholates) based on 1,1′-spirobis[3,3-dimethylindanequinone-5,6]: Spectroscopic and electrochemical studies

Triaryl- and trialkylantimony(V) Bis(catecholates) based on 1,1′-spirobis[3,3-dimethylindanequinone-5,6]: Spectroscopic and electrochemical studies

Synthesis, chemical properties, and crystal structure of 2,4,6,8-tetra(tert-butyl)-9-hydroxyphenoxazin-1-one

[3+1+1] Annulation Reaction of Benzo‐1,2‐Quinones, Aldehydes and Hydroxylamine Hydrochloride: Access to Benzoxazoles with Inorganic Nitrogen Source

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