20146-26-3

Upstream product

• 611-35-8 4-chloroquinoline 
• 108-98-5 thiophenol 
• 56-57-5 4-nitroquinoline-N-oxide 
• 930-69-8 sodium thiophenolate 
• 13133-62-5 thiophenolate 
• 115913-62-7 4-(phenylthio)quinoline 1-oxide 
• 5332-24-1 3-bromoquinoline 
• 3964-04-3 4-bromoquinoline 
• 882-33-7 diphenyldisulfane 

Relevant academic research and scientific papers

Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines: A convenient access to functionalized quinolines

2-, 3- and 4-bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10°C by treatment with Bu3MgLi in THF or toluene. The resulting organomagnesium derivatives were quenched by various electrophiles to afford functionalized quinolines.

Efficient nucleophilic substitution reactions of quinolyl and isoquinolyl halides with nucleophiles under focused microwave irradiation

Nucleophilic substitution reactions of 2-chloroquinoline, 3-bromoquinoline and 4-bromoisoquinoline with thiolate, alkoxy ions and aniline were completed within several minutes under microwave irradiation. This method gives the desired products with yields up to 99% in a short reaction time, and is superior to the classical heating process.

Synthesis and reactivity of lithium tri(quinolinyl)magnesates

2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolinyl)magnesates at -10°C when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines.

Complex base-induced generation of 3,4-dehydroquinoline: A new access to quinoline derivatives

3,4-Dehydroquinoline was easily generated from 3-bromoquinoline and a complex base NaNH2-tBuONa. Nucleophilic condensation of amines and thiolates were performed in good yields.

Conformational Effects in the Alkali-Metal Reduction of Diaryl Sulfides. 2. Evidence for Episulfide Intermediates

Alkali-metal reduction of a series of diaryl sulfides shows that, if both aryl moieties possess aromatic stabilization energies less than that of the phenyl group ( i.e., able to generate relatively more stable radical anions), the diaryl sulfide forms an episulfide intermediate via regiospecific coupling of the aryl moieties at the stage of a reactive intermediate.The formation of the episulfide intermediate explains why double carbon-sulfur bond cleavage and extrusion of sulfur is observed only in such diaryl sulfides and why there is preference for the formation ofsingle regioisomeric biaryl.

Nucleophile and Aryl Radical Reactivity in SRN1 Aromatic Nucleophilic Substitution Reactions. Absolute and Relative Electrochemical Determination

Three electrochemical methods are used to obtain the rate of the Ar.+Nu- reaction.In the direct cyclic voltammetric method, the data are derived from the decrease of the substrate peak current upon addition of the nucleophile while in the relative method they are obtained from the peak heights of the two substitution products observed upon repetitive cycling of the substrate solution in the presence of two nucleophiles.In the redox catalysis method , the reduction of the substrate is catalyzed by an exogeneous reversible couple and the data are derived from the decrease of the catalytic current upon addition of the nucleophile.All three methods were combined to determine the reactivities of a series 26 aryl radical-nucleophile couples.In most cases, the rate constant is close to the diffusion limit.The exceptions concern the 2-quinolyl and 2-pyridyl radicals.The results are discussed in terms of energy difference between the ?* and ?* orbitals in the driving force of the reaction as related to characteristic standard potentials and bond energies.