54988-91-9

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 530-48-3 1,1-Diphenylethylene 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 26037-61-6 2-bromo-3-methoxy-1,4-naphthoquinone 
• 13243-65-7 2,3-Dibromo-1,4-naphthoquinone 
• 72853-79-3 2-(2,2,-diphenylethenyl)-3-methoxy-1,4-naphthoquinone 
• 1010-60-2 2-chloro-1,4-naphthoquinone 

Downstream Products

• 54988-92-0 5-phenyltetraphene 
• 54988-93-1 methyl 4-phenyl-2-naphthoate 

Relevant academic research and scientific papers

Photocycloaddition of arylethenes to 2-substituted-l,4-naphthoquinoncs and reactions of the cyclobutane adduct isomers

The photoreactions of 2-chloro-, 2-bromo-, 2,3-dichloro- and 2,3-bromo-l,4-naphthoquinones with arylethenes are dependent on the addend structure. Cyclobutane adducts are formed from styrene, 1,1-diphenylethene undergoes photosubstitution to give photolabile l,l-diphenyl-l,3-diene derivatives, and spiro-oxetanes are the main products with fra/u-stilbene. 2-Acetoxy-l,4-naphthoquinone undergoes efficient (2n + 2n) photocycloaddition to isobutene, styrene and 1,1-diphenylethene but fra/w-stilbene yields the spiro-oxetane, 3′,4′-diphenyl-3-acetoxyspiro[naphthalene-l,2′-oxetan]-4(lH)- one, 34 regiospecifically. The isobutene adduct, l,l-dimethyl-8a-acetoxy-l,2,2a,8a-tetradihydrocyclobuta[6]naphthalene-3,8-dione, 27 reacts readily with potassium /e/7-butoxide to yield l,l-dimethyI-l,2-dihydrocyclobuta[6]naphthaIene-3,8-dione 11 and is hydrolysed under acid conditions to the corresponding alcohol. In contrast the acetoxycyclobutanes from styrene and 1,1-diphenylethene give only the quinone dimers on base treatment, and under the acid conditions of its formation, the alcohol from the styrene adducts rearranges to 1-hydroxy-l l-e.Yo-phenyltricyclo[7.2.1.02,7]dodeca-2,4,6-triene-8,12-dione 39 while the adduct from the latter arylethene undergoes formal loss of hydrogen to give the red photolabile 3-(2′,2′-diphenylethenyl)-2-hydroxy-l,4-naphthoquinone 42. The Royal Society of Chemistry 2000.

Transition metal-free cyclobutene rearrangement in fused naphthalen-1-ones: Controlled access to functionalized quinones

The controlled synthesis of 1,4-naphthoquinones and tetraphene-7,12-diones, which bear the ABCD-ring of landomycins, has been accomplished directly through oxidative rearrangement of common stable precursors, namely, previously non-isolable cyclobuta[a]naphthalen-4(2H)-ones.

Photoreactions of Halogeno-1,4-naphthoquinones with Electron-rich Alkenes

Photochemical reactions of 2,3-dichloro-1,4-naphthoquinone with 1,1-diarylethylenes or the related electron-rich alkenes have been investigated by steady-state photoreactions, flash photolysis, and kinetic analyses based on the Stern-Volmer experiment and concentration dependence of quantum yields; there is reasonable agreement between them.In acetonitrile a radical ion pair composed of a quinone radical anion and a 1,1-diarylethylene radical cation was observed, while no intermediate was observed in benzene.Dimerization products derived from radical cations were obtained only in the photoreaction of quinone with 1,1-bis(4-methoxyphenyl)ethylene.

Photoinduced Electron-Transfer-Initiated Aromatic Cyclization

Photochemical reaction of substituted 1,4-naphthoquinones with 1,1-diarylethylenes led primarily to benzanthracene-7,12-dione derivatives.Evidence was obtained that the photoreaction proceeded via a photoinduced electron-transfer process.Extension of t

Photochemical Synthesis of Heteroatom-Containing Polycyclic Aromatic Compounds (1a-d)

Anthrafuran, anthrabenzofuran, anthrathiophene, anthrathiophene, anthrabenzothiophene, anthrapyrrole and naphtocarbazole derivatives were synthesized in fairly good yields by a one-pot photocycloaddit

Facile Photochemical Synthesis of Polycyclic Aromatic Compounds

A variety of polycyclic aromatic quinones, which easily reduced to the corresponding aromatic hydrocarbons, were synthesized via one-pot photocycloaddition reaction of simple 2-halogenated 1,4-naphthoquinone derivatives with 1,1-disubstituted ethylenes.Th