Accession Number : AD0904111

Title :   Reactions of Tetrakis(Dimethylamino)Ethylene with Weak Acids.

Descriptive Note : Technical publication,

Corporate Author : NAVAL WEAPONS CENTER CHINA LAKE CA

Personal Author(s) : Norris, William P.

Report Date : OCT 1972

Pagination or Media Count : 20

Abstract : Tetrakis(dimethylamino)ethylene reacts in methanol at 25 degrees to give carbon-carbon bond cleavage, substitution of methoxyl for dimethylamino and addition of methanol to the double bond. The principal products are dimethylamine, dimethoxydimethylaminomethane and 1,1,2-trimethoxy-1,2-bis(dimethylamino)ethane. Minor products are methoxydimethylamino-N,N-dimethylacetamide, trimethylamine and dimethyl ether. An oxidation-reduction side reaction forms a very small amount of the radical cation of tetrakis(dimethylamino)ethylene. In the presence of sodium methoxide no carbon-carbon bond cleavage occurs and no radical cation is formed. When methanol is dissolved in tetrakis(dimethylamino)ethylene(methanol 1M), the principal products are 1,1,2-trimethoxy-1,2-bis(dimethylamino)ethane and dimethylamine with small amounts of tris(dimethylamino)methoxyethylene and 1,2-bis(dimethylamino)-1,2-dimethoxyethylene. Tetrakis(dimethylamino)ethylene and water give dimethylamine and dimethylformamide. (Author)

Descriptors :   (*ETHYLENES, OXIDATION REDUCTION REACTIONS), (*MARKERS, CHEMILUMINESCENCE), (*CHEMILUMINESCENCE, ETHYLENES), CARBINOLS, CARBON, CHEMICAL BONDS, SUBSTITUTION REACTIONS, IONS, SODIUM COMPOUNDS, WATER, CATALYSTS, PROTONS, ILLUMINATION, AMINES, ETHYLENEDIAMINE, FLUOROAMINES, SYNTHESIS(CHEMISTRY), OXIDATION, CHEMICAL REACTIONS, ACIDS.

Subject Categories : Organic Chemistry
      Physical Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE