Radical-anions of aromatic compounds. VII. Reaction of the products from the reduction of nitrobenzene by sodium with isopropyl and tert-butyl iodides (in Russian)
The reaction of the products from the reduction of nitrobenzene by one and two equivalents of sodium with isopropyl iodide leads to the formation of N,O-diisopropylphenylhydroxylamine, while the reaction with tert-butyl iodide leads to p-(tert-butyl)nitrobenzene. Such a change in the nature of the reaction product in the transition from the primary and secondary alkyl halides to the tertiary alkyl halides clearly results from a change in the S/sub N/2 mechanism to the S/sub RN/1 mechanism, involving transfer of an electron from the radical-anion or dianion of nitrobenzene to the alkyl halide. The formation of considerable amounts of azoxybenzene in the reaction with tert-butyl iodide shows that the dianion and, to a lesser degree, the radical-anion of nitrobenzene exhibit basic characteristics.
- Research Organization:
- Novosibirsk Institute of Organic Chemistry, USSR
- OSTI ID:
- 6136990
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:4; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- Russian
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ALKALI METALS
ALKYLATION
AMINATION
AMINES
ANIONS
AZO COMPOUNDS
CHARGED PARTICLES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
ELECTRON TRANSFER
ELEMENTS
ENERGY
HALOGENATED ALIPHATIC HYDROCARBONS
IODINATED ALIPHATIC HYDROCARBONS
IONS
MAGNETIC PROPERTIES
MAGNETIC SUSCEPTIBILITY
MASS SPECTRA
METALS
MOLECULAR IONS
MOLECULAR STRUCTURE
NITRO COMPOUNDS
NITROBENZENE
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHYSICAL PROPERTIES
REDOX POTENTIAL
REDUCING AGENTS
REDUCTION
SODIUM
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
YIELDS