Acetylene Radical-Cations in Carbon-Carbon Bond Forming Reactio

作者：Vasilyev Aleksander V^*

来源：Mini-Reviews in Organic Chemistry, 2017, 14(3): 204-216.

DOI：10.2174/1570193X14666170208101802

• Acetylene radical-cations
• carbon-carbon bond forming reactions
• oxidative dimerization
• ESR spectroscopy
• cyclic voltammetry
• oxidation of acetylene

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.

• 出版日期2017