Heterocyclic cation radicals (review)

Морковник, А. С.; Okhlobystin, O. Yu.

doi:10.1007/bf00513155

Cited by 3 publications

(2 citation statements)

References 174 publications

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“…The electrochemical oxidation of carbazole (CBZ) and its derivatives is a promising method to synthesize dimeric indole alkaloids and prepare polycarbazoles, − which are very useful materials in making sensors and photovoltaic devices. , Due to the planar geometry of the carbazole moiety, these electrochemically generated carbazole radical ions are unstable and react rapidly via dimerization reaction. − …”

Section: Introductionmentioning

confidence: 99%

Capture of Electrochemically Generated Fleeting Carbazole Radical Cations and Elucidation of Carbazole Dimerization Mechanism by Mass Spectrometry

et al. 2020

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The capture of reactive intermediates is important for the elucidation of reaction mechanisms. We report the first observation of electrochemically generated, short-lived radical cations of carbazole (t 1/2 ≈ 97 μs) and two N-substituted carbazole derivatives by mass spectrometry. In addition, online investigation of the reactivity of electrochemically generated carbazole radical cations supports that the carbazole dimerization mechanism involves the reaction of one radical cation with one neutral molecule rather than the previously proposed coupling of two radical cations.

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Section: Introductionmentioning

confidence: 99%

Capture of Electrochemically Generated Fleeting Carbazole Radical Cations and Elucidation of Carbazole Dimerization Mechanism by Mass Spectrometry

et al. 2020

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“…Noticeable instability of DC of 2 formed at the potential of the second oxidation peak is related, most likely, to proton elimination from the methyl group in position 2 (see also Ref. [12]). In fact, when the methyl groups are replaced by the tert-butyl groups, the ECO of dinitron 4 in MeCN at Т = 298 K is an EE process with formation of stable RC and DC in the whole studied range of v (see Fig.…”

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confidence: 94%

Electrochemical Reduction, Oxidation and Molecular Ions of 3,3´-bi(2-R-5,5-dimethy-1-4- oxopyrrolinylidene) 1,1´-dioxides

Shundrin¹

2012

Recent Trend in Electrochemical Science and Technology

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Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions

et al. 2020

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The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.

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Heterocyclic cation radicals (review)

Cited by 3 publications

References 174 publications

Capture of Electrochemically Generated Fleeting Carbazole Radical Cations and Elucidation of Carbazole Dimerization Mechanism by Mass Spectrometry

Capture of Electrochemically Generated Fleeting Carbazole Radical Cations and Elucidation of Carbazole Dimerization Mechanism by Mass Spectrometry

Electrochemical Reduction, Oxidation and Molecular Ions of 3,3´-bi(2-R-5,5-dimethy-1-4- oxopyrrolinylidene) 1,1´-dioxides

Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions

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