Ion-Radical Organic Chemistry

Todres, Zory Vlad

doi:10.1201/9780203909393

Cited by 25 publications

(20 citation statements)

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“…[18] The measured pK a values of protonated nitrobenzene (À11.3) indicates that nitrobenzene itself has weak basic properties. [19] It thus seems reasonable to assume that there is no reaction between the nitrobenzene derivatives and TFA.…”

Section: Methodsmentioning

confidence: 99%

“…However, the literature is replete with nitro compounds undergoing a one-electron reduction, giving rise to radical anions. [18][19][20] An analogous oxidation process has long been observed with various electron-rich substrates. Hence a single-electron transfer (SET) might also be envisioned as the first step in the reaction of a nitrobenzene derivative (e.g., 4) with 2, the resultant radical-anion 33 and radical-cation 34 then undergoing either a stepwise or a concerted cyclization process (Scheme 3, path b).…”

Section: Methodsmentioning

confidence: 99%

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Facile Dearomatization of Nitrobenzene Derivatives and Other Nitroarenes with N‐Benzyl Azomethine Ylide

2010

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Facile Dearomatization of Nitrobenzene Derivatives and Other Nitroarenes with N‐Benzyl Azomethine Ylide

2010

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“…It is reduced when reactions are carried out in a polar reaction medium, thus stabilizing the ions with respect to back electron transfer. Most frequently, in the case of organic compounds, radical ions are generated . These intermediates may generate final products, or they may lead to neutral radical intermediates.…”

Section: Reactions Induced Directly By Photochemical Electron Transfermentioning

confidence: 99%

Electron and hydrogen transfer in organic photochemical reactions

Hoffmann

2014

J of Physical Organic Chem

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Electron and hydrogen transfers are basic steps in many chemical reactions. Photochemical or electronic excitation significantly influences the reactivity of chemical compounds and thus also these transfer processes. Furthermore, the formation of typical intermediates has a decisive impact on the outcome of the transformations. Based on these properties of photochemical processes, efficient homogeneous and heterogeneous photocatalytic transformations for application to organic synthesis have been developed. Efficient reactions without any chemical activation but induced by photochemical electron transfer can also be carried out. The photon acts as a traceless reagent. In the context of photochemical hydrogen transfer, two processes are frequently encountered. The two particles the electron and the proton are transferred either simultaneously or in two steps. In the latter case, the electron is transferred first and the proton follows. Both processes are applied to organic synthesis. Copyright © 2014 John Wiley & Sons, Ltd.

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“…[34] The release of one electron by electron-rich molecules (including amines) is also a well-documented process. [35] Hence, a one-electron transfer from ylide 4 a to, for example, nitrated substrate 45 would result in the formation of radical anion 98 a and radical cation 99 a (Figure 15). Coupling followed by cyclization would deliver the primary cycloadduct.…”

Section: Entrymentioning

confidence: 99%

Aromatic CC Bonds as Dipolarophiles: Facile Reactions of Uncomplexed Electron‐Deficient Benzene Derivatives and Other Aromatic Rings with a Non‐Stabilized Azomethine Ylide

Lee

Diab

Queval

et al. 2013

Chemistry A European J

106

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Non-stabilized azomethine ylide 4a reacts smoothly at room temperature with a variety of uncomplexed aromatic heterocycles and carbocycles on the condition that the ring contains at least one or two electron-withdrawing substituents, respectively. Aromatic substrates, including pyridine and benzene derivatives, participate as 2π components in [3+2] cycloaddition reactions and interact with one, two, or three equivalent(s) of the ylide, depending on their structure and substitution pattern. Thus, this process affords highly functionalized polycyclic structures that contain between one and three pyrrolidinyl ring(s) in useful yields. These results indicate that the site selectivity of the cycloaddition reactions strongly depends on both the nature and the positions of the substituents. In most cases, the second 1,3-dipolar reaction occurs on the opposite face to the one that contains the first pyrrolidinyl ring. DFT calculations on model compounds indicate that a concerted mechanism features a low activation barrier.

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Ion-Radical Organic Chemistry

Cited by 25 publications

References 0 publications

Facile Dearomatization of Nitrobenzene Derivatives and Other Nitroarenes with N‐Benzyl Azomethine Ylide

Facile Dearomatization of Nitrobenzene Derivatives and Other Nitroarenes with N‐Benzyl Azomethine Ylide

Electron and hydrogen transfer in organic photochemical reactions

Aromatic CC Bonds as Dipolarophiles: Facile Reactions of Uncomplexed Electron‐Deficient Benzene Derivatives and Other Aromatic Rings with a Non‐Stabilized Azomethine Ylide

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