Synthesis and characterization of 2,6-di-tert-butyl-1-thio-1,4-benzoquinone, the first isolable monothio-1,4-benzoquinone

Suzuki, Riho; Matsumoto, Kouzou; Kurata, Hiroyuki; Oda, Masaji

doi:10.1039/b003330h

Cited by 22 publications

(34 citation statements)

References 9 publications

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“…This thiocarbonyl stretching frequency is lower than that of the free monothio-1,4-benzoquinone (1141 cm -1 ). [3] Such a trend has been observed for the C=O vibration in the related free and metallated 1,4-benzoquinone. [12] It is worth mentioning that infrared data for o-and p-dithiobenzoquinone complexes have not been reported before.…”

Section: Introductionmentioning

confidence: 82%

“…[2] Recently Oda and co-workers reported the synthesis of 2,6-di-tert-butyl-1-thio-1,4-benzoquinone, where the presence of two tert-butyl groups at the 2-and 6-positions offers steric protection and increases the stability of the mono-thiobenzoquinone. [3] More recently, Cava and co-workers reported the synthesis of dithioanthraquinone analogue in 16 % yield by several steps: first annelation of thiophene rings to benzoquinone produced the anthraquinone analogue, and subsequent treatment with Lawesson's reagent The isomeric o-dithiobenzoquinone (1) has proven to be even more elusive. Three attempts to generate this compound have been recorded.…”

Section: Introductionmentioning

confidence: 99%

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ortho‐ and para‐Thioquinonoid π‐Complexes: First Synthesis, Reactivity, and Crystal Structure Determination

et al. 2007

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Overcoming a long‐standing challenge, the o‐ and p‐dithiobenzoquinone iridium complexes [Cp*Ir‐o‐(η4‐C6H4S2)] (6) and [Cp*Ir‐p‐(η4‐C6H4S2)] (7) were rationally synthesized and fully characterized for the first time including the X‐ray molecular structure of [Cp*Ir‐p‐(η4‐C6H4S2)] (7). Our strategic approach involves the preparation of the halogenated 1,2‐ and 1,4‐dichloro arene π complexes [Cp*Ir‐o‐(η6‐C6H4Cl2)][BF4]2 (4) and [Cp*Ir‐p‐(η6‐C6H4Cl2)][BF4]2 (5), which are the key molecules for 6 and 7. Subsequent treatment of 4 and 5 with NaSH and halogen displacement provides the target thioquinonoid π complexes 6 and 7 in 88 % and 95 % yields respectively. Further, the coordination chemistry of the o‐dithiobenzoquinone iridium complex [Cp*Ir‐o‐(η4‐C6H4S2)] (6) was studied by treating 6 with [(bpy)PtCl2] in the presence of AgOTf, which provided the novel platinum complex [Pt(bpy){Cp*Ir‐o‐(η4‐C6H4S2)}][OTf]2 (10) in 91 % yield. The X‐ray molecular structure of 10 is reported and shows as outstanding features the formation of 1D supramolecular assembly, which results from π–π (d = 3.484 Å; d = 3.669 Å) and Pt···Pt (d = 3.574 Å) interactions between individual subunits.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Introductionmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

ortho‐ and para‐Thioquinonoid π‐Complexes: First Synthesis, Reactivity, and Crystal Structure Determination

et al. 2007

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“…The formation of the corresponding disulfide by the oxidation of the hydroxybenzenethiol was reported for 3a and 4a [5,7].…”

Section: Synthesis and Structurementioning

confidence: 95%

“…[3a], 758, 456sh, 321 (3a) [5], and 422 (4a) [7]). The latter can be assigned to the decomposition products, which still contain thiocarbonyl groups.…”

Section: Oxidation Of 4-hydroxybenzenethiol 5 and 44 -Dihydroxydiphementioning

confidence: 99%

Synthesis, Structure, and Reactivity of 2,6‐Diaryl‐4‐hydroxybenzenethiol

Sasaki

Sutoh

Yoshifuji

2014

Heteroatom Chemistry

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“…Im Unterschied zu den Benzochinonen sind die Schwefelanaloga hoch reaktiv, was ihre Handhabung und Isolierung in reiner Form erschwert. [53,54] Beispiele für isolierte Thiochinone sind daher spärlich; tatsächlich konnte p-Dithiobenzochinon (7) nur bei 10 K in einer Argonmatrix erzeugt und spektroskopisch charakterisiert werden, da es bei mäßiger Erwärmung der Matrix auf nicht bekannte Weise zerfällt. [55] Als noch schwieriger erwies sich das o-Dithiobenzochinon (6).…”

Section: Neutrale O-und P-dithiobenzochinon-iridiumlinkerunclassified

Supramolekulare Aggregate mit metallorganischen Chinon‐Linkern: eine neue Klasse von Koordinationsnetzwerken

Moussa

Amouri

2008

Angewandte Chemie

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Ein derzeit sehr aktives Forschungsgebiet befasst sich mit der Synthese und Anwendung von Koordinationsnetzwerken, die im Allgemeinen aus organischen Linkern und Übergangsmetallen aufgebaut sind. Wir beschreiben hier eine neuartige Klasse von supramolekularen Strukturen mit metallorganischen Linkern in Form von Chinon‐ und Thiochinon‐Komplexen der allgemeinen Formel [Cp*M(η4‐Benzochinon)] (o‐ und p‐Benzochinon, Cp*=C5Me5, M=Rh, Ir) und [Cp*Ir(η4‐Thiobenzochinon)] (o‐ und p‐Thiobenzochinon), die mit ihren freien O‐ bzw. S‐Atomen an Metallionen wie CuI, AgI oder PtII binden und Koordinationsnetzwerke bilden. Hierbei fungieren die Chinon‐ oder Thiochinon‐Komplexe als Gerüste und die Metallzentren als Knotenpunkte. Eine Besonderheit dieser Strukturen sind die kurzen π‐π‐ und M⋅⋅⋅M‐Abstände, die zu nützlichen photophysikalischen Eigenschaften führen. Mit den hier beschriebenen Bausteinen ist eine Vielzahl supramolekularer Architekturen zugänglich, die sich zur Entwicklung funktioneller Materialen anbieten.

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Synthesis and characterization of 2,6-di-tert-butyl-1-thio-1,4-benzoquinone, the first isolable monothio-1,4-benzoquinone

Cited by 22 publications

References 9 publications

ortho‐ and para‐Thioquinonoid π‐Complexes: First Synthesis, Reactivity, and Crystal Structure Determination

ortho‐ and para‐Thioquinonoid π‐Complexes: First Synthesis, Reactivity, and Crystal Structure Determination

Synthesis, Structure, and Reactivity of 2,6‐Diaryl‐4‐hydroxybenzenethiol

Supramolekulare Aggregate mit metallorganischen Chinon‐Linkern: eine neue Klasse von Koordinationsnetzwerken

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