Anodic Reactions of Alkanes, Alkenes, and Aromatic Compounds

Abstract

The sections in this article are Introduction Anodic Oxidation of Alkanes Anodic Substitution of CH Bonds Oxidation of Remote CH Bonds in Ketones, Carboxylic Acids, and Steroids C , C Bond Cleavage in Hydrocarbons Oxidation of Hydrocarbons in Fuel Cells Anodic Oxidation of Alkenes General Reaction Behavior Anodic Coupling of Alkenes by Way of Radical Cations Intermolecular Coupling Intramolecular Coupling Anodic Substitution and Addition via Radical Cations Addition via Oxidation of Nucleophiles to Radicals Mediated Oxidation of Alkenes Anodically Induced Cycloadditions Anodic Oxidation of Aromatic Compounds General Principles of Reaction Anodic Coupling Nuclear Aromatic Substitution Anodic Side Chain Substitution of Aromatic Compounds Anodic Addition Comparison of Anodic Conversions of Alkanes, Alkenes, and Aromatic Compounds with their Chemical Transformations

Infrared Spectroscopic Investigation of the Acidic CH Bonds in Cationic n-Alkanes: Pentane, Hexane, and Heptane

“…Therefore, CH bond properties of alkane radical cations would differ from those of alcohols, ethers, and amine, in which the ejection from the nonbonding orbital of the heteroatom preferentially occurs in ionization and hyperconjugation with the nonbonding orbital plays a key role in the properties of the acidic CH bond. Alkane radical cations are often seen as precursors and reaction intermediates in synthetic chemistry, electrochemistry, radiation chemistry, and interstellar chemistry. − Therefore, microscopic level understanding of their properties would contribute to elucidate such chemical processes involving alkane cations. Alkanes have undergone photoelectron spectroscopy and theoretical investigations. − Low-energy features in their photoelectron spectra have been interpreted as ejection of an electron from delocalized orbitals through pseudo π orbitals (π-type orbitals) of CH bonds and σ orbitals of C–C bonds.…”