Acetylene Radical-Cations in Carbon-Carbon Bond Forming Reactio ns

Author(s): Aleksander V. Vasilyev*

Journal Name: Mini-Reviews in Organic Chemistry

Volume 14 , Issue 3 , 2017

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Graphical Abstract:


This review surveys carbon-carbon bond forming reactions of acetylene radical-cations, generated under the one-electron oxidation of alkynes in the systems lead dioxide (PbO2) – strong acid (CF3CO2H, FSO3H, HF). The oxidative dimerization proceeds very regioselectively at acetylene carbons. This approach is a powerful synthetic tool, leading to complex and polyfunctional organic molecules, such as, dicarbonyl- and tetracarbonyl-substituted ethylenes, 1,4-difluoro- and 1,4- dichlorobutadienes, etc. Reaction mechanisms of acetylene radical-cations are considered. The reactivity of acetylene radical-cations may be explained by their electronic structure, determined by means of electron spin resonance spectroscopy and cyclic voltammetry.

Keywords: Acetylene radical-cations, carbon-carbon bond forming reactions, oxidative dimerization, ESR spectroscopy, cyclic voltammetry, oxidation of acetylene.

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Article Details

Year: 2017
Published on: 03 July, 2017
Page: [204 - 216]
Pages: 13
DOI: 10.2174/1570193X14666170208101802
Price: $65

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