Double addition of diethylamine to biacetylene

Journal Article · Sat Mar 01 00:00:00 EST 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6191051

Trofimov, B A; Vavilova, A N

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), Vol. 22:3; Other Information: Translated from Zh. Org. Khim.; 22: No. 3, 475-478(Mar 1986)
• Country of Publication: United States
• Language: Russian

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ALKYNES
AMINATION
AMINES
ACTIVATION ENERGY
DIENES
HYDRATION
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
ACETONITRILE
ADDUCTS
CHEMICAL REACTION KINETICS
CHEMICAL SHIFT
ETHANOL
HYDRATES
HYDROGEN TRANSFER
INFRARED SPECTRA
KETONES
KINETIC EQUATIONS
LINE WIDTHS
METHANOL
NMR SPECTRA
REACTION INTERMEDIATES
SOLVENT PROPERTIES
SPECTRAL SHIFT
TETRAHYDROFURAN
ULTRAVIOLET SPECTRA
ALCOHOLS
CHEMICAL REACTIONS
ENERGY
EQUATIONS
FURANS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
KINETICS
NITRILES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POLYENES
REACTION KINETICS
SOLVATION
SPECTRA
400201* - Chemical & Physicochemical Properties