Use of tetrabutylammonium cyanide for photocyanation of aromatic compounds: phase transfer photochemistry

Beugelmans, R.; Ginsburg, H.; Lecas, Alexandra; Goff, Marie-Thérèse Le; Pusset, J.; Roussi, G.

doi:10.1039/c39770000885

Cited by 11 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Indeed, Beugelmans et al reported that the photocyanation yields of nitroaromatics in a methylene chloride/water/KCN system were improved by adding tetrabutylammonium cyanide as a catalyst. 43,44 If ion pair formation between a dodecyltrimethylammonium cation and a cyanide anion proceeds and the ion pairs distribute to the oil phase to some extent, the photoreaction takes place partly in the oil droplet, leading to the increase in the reaction efficiency. Therefore, we consider that the surfactant effects on F CN originate from cooperative effects by formation of the electric double layer at the interface and ion pair extraction of cyanide ions to the oil phase.…”

Section: Surfactant Effects On U Cnmentioning

confidence: 99%

A laser trapping-spectroscopy study on the photocyanation of perylene across a single micrometre-sized oil droplets/water interface: droplet-size effects on photoreaction quantum yield

Kitagawa

Kitamura

2002

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

Section: Surfactant Effects On U Cnmentioning

confidence: 99%

A laser trapping-spectroscopy study on the photocyanation of perylene across a single micrometre-sized oil droplets/water interface: droplet-size effects on photoreaction quantum yield

Kitagawa

Kitamura

2002

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

“…15-19,34, 35 Beugelmans et al 36,37 have reported an interesting synthetic example dealing with the photocyanation reactions of aromatic hydrocarbons with KCN and a crown ether or tetrabutylammonium cyanide in a water-dichloromethane system. 15-19,34, 35 Beugelmans et al 36,37 have reported an interesting synthetic example dealing with the photocyanation reactions of aromatic hydrocarbons with KCN and a crown ether or tetrabutylammonium cyanide in a water-dichloromethane system.…”

Section: Discussionmentioning

confidence: 99%

“…Applications of a PTC technique in photochemistry are quite rare. 15-19,34, 35 Beugelmans et al 36,37 have reported an interesting synthetic example dealing with the photocyanation reactions of aromatic hydrocarbons with KCN and a crown ether or tetrabutylammonium cyanide in a water-dichloromethane system. We recently studied the effect of addition of an ammonium salt, serving as a surfactant, into the two-phase reaction system.…”

Section: Discussionmentioning

confidence: 99%

Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole

Klán

Ruzicka

Heger

et al. 2002

Photochem Photobiol Sci

View full text Add to dashboard Cite

A temperature-sensitive photochemical nucleophilic aromatic substitution on 4-nitroanisole by a hydroxide ion in homogeneous solutions, in a two-phase system under phase-transfer catalysis conditions, and in the microwave field is reported. It was found that reaction regioselectivity dramatically changes with temperature in the region of -20 to 196 degrees C. The quantum yield of the 4-methoxyphenol formation was found to be temperature independent, in contrast to that of the 4-nitrophenol formation, suggesting that there is a temperature dependent process occurring after the partitioning between replacement of the nitro group and the methoxy group has taken place. The reaction was also investigated by using quantum chemical calculations. A technique for microwave-assisted photochemical synthesis is proposed as an efficient and practical tool for organic synthesis.

show abstract

“…After these reports, various attempts have been conducted to improve the reaction yield. As an example, Beugelmans et al reported that the product yield could be improved by using aprotic solvent-crown ether combinations to dissolve alkali cyanide 9 as well as by employing a phase-transfer catalyst. 10 The efficiency of photocyanation reaction is also dependent on the number of the aromatic rings ArH.…”

Section: Introductionmentioning

confidence: 99%

A Mechanistic Study of Photocyanation of Pyrene in Oil-in-Water Emulsion Systems

2002

View full text Add to dashboard Cite

A highly efficient one-step photocyanation reaction of pyrene was shown to proceed in oil-in-water emulsion systems. As a typical example, photoirradiation of pyrene in the presence of 1,4-dicyanobenzene and NaCN in a benzonitrile/water mixture (1/100, vol %) under vigorous stirring gave 1-cyanopyrene in a conversion yield of 83%, while an analogous reaction in an acetonitrile/water mixture (9/1, vol %) yielded this product in 61% yield. We evaluated the quantum yield of photocyanation in the oil-in-water emulsion system to be 0.17. Under optimum conditions, the quantum yield was improved to 0.68. Characteristics and possible mechanisms of the photocyanation reaction are discussed in detail.

show abstract

Use of tetrabutylammonium cyanide for photocyanation of aromatic compounds: phase transfer photochemistry

Cited by 11 publications

References 0 publications

A laser trapping-spectroscopy study on the photocyanation of perylene across a single micrometre-sized oil droplets/water interface: droplet-size effects on photoreaction quantum yield

A laser trapping-spectroscopy study on the photocyanation of perylene across a single micrometre-sized oil droplets/water interface: droplet-size effects on photoreaction quantum yield

Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole

A Mechanistic Study of Photocyanation of Pyrene in Oil-in-Water Emulsion Systems

Contact Info

Product

Resources

About