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:

1972-10-01

Pagination or Media Count:

20.0

Abstract:

Tetrakisdimethylaminoethylene 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-bisdimethylaminoethane. 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 tetrakisdimethylaminoethylene. In the presence of sodium methoxide no carbon-carbon bond cleavage occurs and no radical cation is formed. When methanol is dissolved in tetrakisdimethylaminoethylenemethanol 1M, the principal products are 1,1,2-trimethoxy-1,2-bisdimethylaminoethane and dimethylamine with small amounts of trisdimethylaminomethoxyethylene and 1,2-bisdimethylamino-1,2-dimethoxyethylene. Tetrakisdimethylaminoethylene 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