Oxidation of alcohols to carbonyl compounds by nitrates and nitrites in aqueous trifluoroacetic acid. Reaction mechanism and unusual stoichiometry of reduction of the oxidizing agent to elemental nitrogen

Journal Article · Wed Aug 10 00:00:00 EDT 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5887602

Rodkin, M A; Shtern, M M; Cheprakov, A V; Makhon'kov, D I; Mardaleishvili, R E; Beletskaya, I P

The oxidation of benzyl alcohols, benzhydrols, and secondary aliphatic alcohols to the corresponding carbonyl compound by alkali-metal and ammonium nitrates and nitrites in aqueous solutions of trifluoroacetic acid was studied. Molecular nitrogen was detected in the gaseous reaction products, and this made it possible to interpret the mechanism as hydride transfer with the formation of nitrosyl hydride HNO. In the presence of oxygen the oxidation of the alcohols can be realized with a catalytic amount of nitrate. The possibilities and limitations of the catalytic version of the reaction are discussed.

• Research Organization: M.V. Lomonosov Moscow State Univ. (USSR)
• OSTI ID: 5887602
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 24:3; Other Information: Translated from Zh. Org. Khim.; 24: No. 3, 488-495 (Mar 1988)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ALCOHOLS
OXIDATION
NITROGEN COMPOUNDS
CATALYTIC EFFECTS
OXIDIZERS
REDUCTION
ACETIC ACID
AMMONIUM NITRATES
AQUEOUS SOLUTIONS
BENZALDEHYDE
CATALYSIS
CATALYSTS
LABELLED COMPOUNDS
MASS SPECTRA
NITRITES
NITROGEN 14
NITROGEN 15
NITROGEN OXIDES
ORGANIC FLUORINE COMPOUNDS
QUANTITY RATIO
RADIOCHEMICAL ANALYSIS
REDOX POTENTIAL
SODIUM COMPOUNDS
SODIUM NITRATES
STOICHIOMETRY
ALDEHYDES
ALKALI METAL COMPOUNDS
AMMONIUM COMPOUNDS
CARBOXYLIC ACIDS
CHALCOGENIDES
CHEMICAL ANALYSIS
CHEMICAL REACTIONS
DISPERSIONS
HYDROXY COMPOUNDS
ISOTOPES
LIGHT NUCLEI
MIXTURES
MONOCARBOXYLIC ACIDS
NITRATES
NITROGEN ISOTOPES
NUCLEI
ODD-EVEN NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
QUANTITATIVE CHEMICAL ANALYSIS
SOLUTIONS
SPECTRA
STABLE ISOTOPES
400201* - Chemical & Physicochemical Properties
400101 - Activation
Nuclear Reaction
Radiometric & Radiochemical Procedures