Double addition of diethylamine to biacetylene (in Russian)
Biacetylene reacts with an excess of diethylamine in dilute solutions of anhydrous acetonitrile, methanol, ethanol, and THF to form the diadduct 1,3-bis(diethyl-amino)-1,3-butadiene (lambda/sub max/ 325 nm). During concentration of the reaction mixture the latter undergoes hydration by the residual amounts of water in the 3-(diethylamino)-2-butenal. The spectral characteristics (UV, IR, PMR) of the intermediate reaction products are given. The kinetics of the stage of addition of the diethylamine and water to the monoadduct, 1-(diethylamino)-1-buten-3-yne, were studied. It was concluded that the addition of the nucleophile to the triple bond during its secondary amination and hydration is facilitated by the concerted transfer of a proton.
- Research Organization:
- Irkutsk Institute of Organic Chemistry, USSR
- OSTI ID:
- 6191051
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:3; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- Russian
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACETONITRILE
ACTIVATION ENERGY
ADDUCTS
ALCOHOLS
ALKYNES
AMINATION
AMINES
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHEMICAL SHIFT
DIENES
ENERGY
EQUATIONS
ETHANOL
FURANS
HETEROCYCLIC COMPOUNDS
HYDRATES
HYDRATION
HYDROCARBONS
HYDROGEN TRANSFER
HYDROXY COMPOUNDS
INFRARED SPECTRA
KETONES
KINETIC EQUATIONS
KINETICS
LINE WIDTHS
METHANOL
NITRILES
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POLYENES
REACTION INTERMEDIATES
REACTION KINETICS
SOLVATION
SOLVENT PROPERTIES
SPECTRA
SPECTRAL SHIFT
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
TETRAHYDROFURAN
ULTRAVIOLET SPECTRA