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

[ Vol. 14 , Issue. 3 ]

Author(s):

Aleksander V. Vasilyev   Pages 204 - 216 ( 13 )

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.

Affiliation:

Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per. 5, Saint Petersburg, 194021

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