Photochemical aromatic alkylation

Kurz, Michael; Noreuil, T.; Seebauer, Joe; Cook, S. E.; Geier, D.; Leeds, Andrea; Stronach, Chuck; Barnickel, Bette; Kerkemeyer, Mark

doi:10.1021/jo00236a034

Cited by 6 publications

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“…In all cases, an initial process leading to the homolytic cleavage of the carbon–halogen (CX) bond with the formation of a pair, alkyl radical–halogen atom, is advocated 8. After this initial process, radical reaction products can be obtained; this process competes with electron transfer in the radical pair within the solvent ‘cage’ thus producing the ion‐pair and finally some characteristic products of the carbocation as intermediate.…”

Section: Introductionmentioning

confidence: 99%

The photoinduced reaction of 2‐iodothiophene in solutions of n‐heptane, dichloromethane and methanol

Herrera

Nieto

Olleta

et al. 2010

J of Physical Organic Chem

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The photoinduced reaction of 2‐iodothiophene in n‐heptane, dichloromethane and methanol was studied at room temperature from experiments carried out with degassed solutions. The photoproducts of the reaction were mainly thiophene and small amounts of iodine in all three solvents used. The concentration of 2‐iodothiophene decreases throughout photolysis, following a first‐order rate law and the pseudo‐first‐order rate constants were determined in the three solvents used. The photochemistry of the system was quantified determining the quantum yields of 2‐iodothiophene consumption and thiophene formation in n‐heptane solutions. The results show that under the experimental conditions of this research, products deriving only from the reaction of the thienyl radical were observed. To support the experimental results, calculations were performed of the ionization potential of the thienyl radical, electron affinity of the iodine atom and free energy of solvation of the corresponding iodide and carbocation in the different solvents used. Copyright © 2010 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

The photoinduced reaction of 2‐iodothiophene in solutions of n‐heptane, dichloromethane and methanol

Herrera

Nieto

Olleta

et al. 2010

J of Physical Organic Chem

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Recent Advances in the Photochemistry of the Carbon–Halogen Bond

Lodder

Cornelisse

2009

Patai's Chemistry of Functional Groups

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Brominated Methanes as Photoresponsive Molecular Storage of Elemental Br₂

Kawakami

Tsuda

2012

Chemistry An Asian Journal

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The photochemical generation of elemental Br2 from brominated methanes is reported. Br2 was generated by the vaporization of carbon oxides and HBr through oxidative photodecomposition of brominated methanes under a 20 W low‐pressure mercury lamp, wherein the amount and situations of Br2 generation were photochemically controllable. Liquid CH2Br2 can be used not only as an organic solvent but also for the photoresponsive molecular storage of Br2, which is of great technical benefit in a variety of organic syntheses and in materials science. By taking advantage of the in situ generation of Br2 from the organic solvent itself, many organobromine compounds were synthesized in high practical yields with or without the addition of a catalyst. Herein, Br2 that was generated by the photodecomposition of CH2Br2 retained its reactivity in solution to undergo essentially the same reactions as those that were carried out with solutions of Br2 dissolved in CH2Br2 that were prepared without photoirradiation. Furthermore, HBr, which was generated during the course of the photodecomposition of CH2Br2, was also available for the substitution of the OH group for the Br group and for the preparation of the HBr salts of amines. Furthermore, the photochemical generation of Br2 from CH2Br2 was available for the area‐selective photochemical bleaching of natural colored plants, such as red rose petals, wherein Br2 that was generated photochemically from CH2Br2 was painted onto the petal to cause radical oxidations of the chromophoric anthocyanin molecules.

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Photochemical aromatic alkylation

Cited by 6 publications

References 1 publication

The photoinduced reaction of 2‐iodothiophene in solutions of n‐heptane, dichloromethane and methanol

The photoinduced reaction of 2‐iodothiophene in solutions of n‐heptane, dichloromethane and methanol

Recent Advances in the Photochemistry of the Carbon–Halogen Bond

Brominated Methanes as Photoresponsive Molecular Storage of Elemental Br₂

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Photochemical aromatic alkylation

Cited by 6 publications

References 1 publication

The photoinduced reaction of 2‐iodothiophene in solutions of n‐heptane, dichloromethane and methanol

The photoinduced reaction of 2‐iodothiophene in solutions of n‐heptane, dichloromethane and methanol

Recent Advances in the Photochemistry of the Carbon–Halogen Bond

Brominated Methanes as Photoresponsive Molecular Storage of Elemental Br2

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Product

Resources

About

Brominated Methanes as Photoresponsive Molecular Storage of Elemental Br₂