The mechanism of anodic oxidation of alkyl iodides. Electrophilicity of iodine(I).

Miller, Larry L.; Watkins, Bruce F.

doi:10.1016/s0040-4039(01)92201-4

Cited by 20 publications

(1 citation statement)

References 4 publications

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“…Polyfluoroalkyl iodides can be transformed anodically into amides, esters, and ethers [7]. Secondary alkyl iodides afford N -alkylacetamides (2) upon oxidation at platinum in acetonitrile [8], and various mechanistic features of the oxidation of both primary and secondary alkyl iodides have been probed [9].…”

Section: Halogenated Alkanesmentioning

confidence: 99%

Oxidation and Reduction of Halogen‐containing Compounds

Peters

2004

Encyclopedia of Electrochemistry

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The sections in this article are Introduction Anodic Processes Halogenated Alkanes Alicyclic Halides Aryl Halides Cathodic Processes Halogenated Alkanes Halogenated Alkenes and Alkynes Benzyl Halides Alicyclic Halides Aryl Halides Acyl and Phenacyl Halides Aliphatic α‐Halocarbonyl Compounds Halogenated Heterocyclic Compounds Catalytic Reduction of Carbon–Halogen Bonds

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Section: Halogenated Alkanesmentioning

confidence: 99%

Oxidation and Reduction of Halogen‐containing Compounds

Peters

2004

Encyclopedia of Electrochemistry

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Indirect Electrochemical Reactions

Torii

2004

Encyclopedia of Electrochemistry

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The sections in this article are Introduction Indirect Electrooxidation Indirect Oxidation with Halide Ions Chloro Cation [ CI ] + ‐assisted Indirect Oxidation Bromo Cation [ Br ] + ‐assisted Indirect Oxidation Indirect Oxidation with [I] + and IO 4 − as Electron Carriers Indirect Oxidation with Organic Mediators Mediators Containing Sulfur and Selenium Elements Mediators Containing Nitrogen Indirect Oxidation with Other Redox Systems Metal Ion‐assisted Indirect Oxidation Indirect Oxidation with Metal Ion Redox Systems Indirect Oxidation with Nickel ( Ni ) and Cobalt ( Co ) Compounds Iron ( Fe ) Complex‐assisted Oxidation Indirect Oxidation with Chromic Acid [ Cr ( VI )] Palladium (Pd)‐assisted Oxidation Ruthenium ( Ru )‐assisted Oxidation Osmium ( Os )‐assisted Oxidation Indirect Oxidation with Manganese [ Mn (III)] Indirect Oxidation with Cerium ( Ce ) Complexes Copper ( Cu ) and Silver ( Ag )‐assisted Oxidation Thallic Ion [ Tl ( III )]‐assisted Oxidation Indirect Electroreduction Indirect Reduction with Mediators Containing Nickel, Cobalt, and Iron Nickel ( Ni ) Complex Mediators Cobalt ( Co ) Complex Mediators Iron ( Fe ) Complex Mediators Indirect Reduction with Mediators Containing Palladium, Rhodium, Iridium, and Platinum Palladium ( Pd ) Complex Mediators Platinum (Pt) Complex Mediators Rhodium and Iridium Complex Mediators Indirect Reduction with Mediators Containing Ruthenium and Osmium Ruthenium ( Ru ) Complex Mediators Osmium ( Os ) Complex Mediators Indirect Reduction with Mediators Containing Chromium, Molybdenum, and Tungsten Chromium ( Cr ) Complex Mediators Molybdenum ( Mo ) Complex Mediators Tungsten (W) Complex Mediators Indirect Reduction with Mediators Containing Manganese and Rhenium Manganese ( Mn ) Complex Mediators Rhenium ( Re ) Complex Mediators Indirect Reduction with Mediators Containing Titanium, Tin, and Lead Titanium ( Ti ) Complex Mediators Tin ( Sn ) Complex Mediators Lead ( Pb ) Complex Mediators Indirect Reduction with Mediators Containing Zinc ( Zn ), Mercury ( Hg ), and Cadmium ( Cd ) Indirect Reduction with Mediators Containing Selenides ( Se ) or Tellurides ( Te ) Indirect Reduction with Mediators Containing Miscellaneous Metal Complexes Samarium ( Sm ) and Indium ( In ) Complex Mediators Antimony ( Sb ) and Bismuth ( Bi ) Complex Mediators Copper ( Cu ) Complex Mediators

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Anodic dehalogenation of 1,2‐dichloroethane in aqueous electrolytes

1990

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Dedicated to Professor Dr. Karl-Hans Simmrock on the occasion of his 60th birthdayA solution of 0.1 M 1,2-dichloroethane in 1 M H2S04 was anodically converted to CO,,CI, and HClO, as the main products at smooth platinum. The current efficiency for COz exceeds 60% at low current densities, while HClO, is obtained with about 20% current efficiency. Chlorinated products such as 1,1',2-trichloroethane are formed in negligible amounts. Platinum plays a distinctive role as anode material and shows a reaction limited anodic prewave. Our experimental findings lead to a mechanism, whereby DCE is initially hydroxylated to form chloroacetaldehyde chlorohydrin which releases HCI and becomes rapidly further oxidized to monochloroacetic acid. The cleavage of the C-C bond proceeds via its anodic decarboxylation. Possible practical applications in the field of anodic water purification and in the direct electrosynthesis of vinyl chloride are discussed.

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The mechanism of anodic oxidation of alkyl iodides. Electrophilicity of iodine(I).

Cited by 20 publications

References 4 publications

Oxidation and Reduction of Halogen‐containing Compounds

Oxidation and Reduction of Halogen‐containing Compounds

Indirect Electrochemical Reactions

Anodic dehalogenation of 1,2‐dichloroethane in aqueous electrolytes

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