Kinetics and mechanism of monomolecular heterolysis of framework compounds. V. Ionization-fragmentation process in decomposition of 1-adamantyl chloroformate
The decomposition of 1-adamantyl chloroformate in acetonitrile, nitrobenzene, benzene, and isopropyl and tert-butyl alcohols in the presence of triphenylverdazyls as internal indicator was investigated preparatively and kinetically. In nitrobenzene small additions of water increase the reaction rate, and additions of tetraethylammonium halides reduce it. In isopropyl and tert-butyl alcohols and in nitrobenzene in the presence of tetraethylammonium halides the reaction rate depends on the nature of the substituent in the verdazyl. The reaction rate increases linearly with increase in the dielectric constant of the medium. It is assumed that an intimate ion pair is formed at the first stage of the reaction and undergoes fragmentation in the controlling stage to 1-adamantyl chloride or is converted into a solvent-separated ion pair. The latter reacts with the verdazyl or undergoes fragmentation to 1-adamantyl chloride.
- Research Organization:
- Kiev Polytechnical Institute (USSR)
- OSTI ID:
- 5950016
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 24:3; Other Information: Translated from Zh. Org. Khim.; 24: No. 3, 535-549 (Mar 1988)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
CARBOXYLIC ACID ESTERS
DECOMPOSITION
ORGANIC CHLORINE COMPOUNDS
ORGANIC IODINE COMPOUNDS
ACETONITRILE
ADAMANTANE
AMMONIUM HALIDES
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHLORINATED ALIPHATIC HYDROCARBONS
CHROMATOGRAPHY
ETHANOL
FORMIC ACID
INDICATORS
INFRARED SPECTRA
IONIZATION
METHANOL
NITROBENZENE
NMR SPECTRA
QUATERNARY COMPOUNDS
SOLVOLYSIS
WATER
ALCOHOLS
ALKANES
AMINES
AMMONIUM COMPOUNDS
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CYCLOALKANES
ESTERS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
KINETICS
MONOCARBOXYLIC ACIDS
NITRILES
NITRO COMPOUNDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN COMPOUNDS
REACTION KINETICS
SEPARATION PROCESSES
SPECTRA
400201* - Chemical & Physicochemical Properties