2,3-Dichloro-5,6-dicyanobenzoquinone and Its Reactions

Walker, Derek; Hiebert, Jack D.

doi:10.1021/cr60246a002

Cited by 488 publications

(211 citation statements)

References 67 publications

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“…In addition, many studies on thermal and photochemical reactions via CT complexes have been reported. [28][29][30][31] Furthermore, p-benzoquinones (Qs) and hydroquinones (QH 2 ) have attracted a great deal of attention because of the role of redox reactions of these Qs in a variety of biochemical electron transport reactions, including the conversion of NADH to NAD ϩ , photosynthetic reactions, and the reduction of cytochrome c. 32,33) In general, halogenated CA and DDQ are not only powerful dehydrogenating reagents 34) for organic compounds such as steroids, but also effective electron-accepting photosensitizers 35) for oxidation of various compounds. Moreover, they can initiate various bond formation or cleavage reactions (e.g., of C-C bond and C-O bonds).…”

mentioning

confidence: 99%

Reactions of 1-Naphthols with .PI.-Acceptor p-Benzoquinones: Oxidative Aryl Coupling vs. Non-Oxidative Electrophilic Arylation

Takeya

Kondo

Otsuka

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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We investigated the reactions of various 1-naphthols (NPOHs; 1) with p-benzoquinones (Qs), such as 1,4-benzoquinone (BQ) and p-chloranil (CA), as p p-electron acceptors. With electron-rich NPOHs 1a-c, oxidative biaryl coupling and subsequent dehydrogenation reaction took place selectively to give the corresponding 2,2Ј-binapthyl-1,1Ј-quinones 3a-c in excellent yield. In the case of electron-deficient NPOHs 1e, f, two different types of reactions occurred in the presence of SnCl 4 and ZrO 2 under similar conditions: SnCl 4 mediated oxidative dimerization and trimerization of NPOH, while ZrO 2 promoted electrophilic arylation of Qs with NPOH. The resulting products 3 would be useful synthetic intermediates for naturally occurring diosindigo B, biramentaceone and violet-quinone.

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mentioning

confidence: 99%

Reactions of 1-Naphthols with .PI.-Acceptor p-Benzoquinones: Oxidative Aryl Coupling vs. Non-Oxidative Electrophilic Arylation

Takeya

Kondo

Otsuka

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Dehydrogenation of 17 with dicyanodichloro-p-benzoquinone (DDQ) 11 in benzene for 12 h at ambient temperature indicated that ketone 17 was consumed but gave an insoluble polymeric material. Repeating the reaction either in the presence of furan or in benzene-d 6 under similar conditions gave the same results.…”

Section: Methodsmentioning

confidence: 99%

DFT calculations of pentalenoquinones: towards the interception of 2-bromopentalene-1,5-dione

Atalar¹,

Algı²,

Balcı³

2008

Arkivoc

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To reveal the stability and the aromatic character of pentalenoquinones (PQs) 1-4 and the corresponding bromo derivatives (Br-PQs) 6-9, DFT calculations (B3LYP/6-311+G(d,p)) concerning the geometry optimization, total energy and nucleus independent chemical shift (NICS) values were performed. It was found that all of the compounds have planar geometry. As the energy difference between HOMO-LUMO energy levels (∆ε=ε LUMO -ε HOMO ) and total energies were considered for the pentalene family, the stability order was found to be 1 > 2 > 3 > 4 for PQs, and 6 > 7 > 8 > 9 for Br-PQs. Furthermore 2-bromopentalene-1,5-dione (6) in solution was investigated and noted that it was too reactive to be isolated or even trapped.

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“…To a solution of 8.8 g of the mixture of diols 10 and 11 (sce above) in 1 1 of dry dioxane was added 10 g of 2,3-dichloro-5,6-dicyanobenzoquinone (15) in 500 ml of dry dioxane. The resulting solution was stirred at room ternperaturc for 4 h, and filtered.…”

Section: Preparation Of Keto Alcohol 14mentioning

confidence: 99%

Conversion of (−)-α-santonin into (+)-α-cyperone

Piers¹,

Cheng²

1968

Can. J. Chem.

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An efficient, 8-step synthesis of (+)-a-cyperone (1) from (-)-a-santonin (5) is described. The key steps of the sequence involve the conversion of the keto ester 8 into the substituted octalone 9, by hydrogenation of the former in the presence of the homogeneous catalyst tris(tripheny1phosphine)-chlororhodium, and the pyrolysis of the keto carbonate 16, which produces (+)-a-cyperone in good yield.

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2,3-Dichloro-5,6-dicyanobenzoquinone and Its Reactions

Cited by 488 publications

References 67 publications

Reactions of 1-Naphthols with .PI.-Acceptor p-Benzoquinones: Oxidative Aryl Coupling vs. Non-Oxidative Electrophilic Arylation

Reactions of 1-Naphthols with .PI.-Acceptor p-Benzoquinones: Oxidative Aryl Coupling vs. Non-Oxidative Electrophilic Arylation

DFT calculations of pentalenoquinones: towards the interception of 2-bromopentalene-1,5-dione

Conversion of (−)-α-santonin into (+)-α-cyperone

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