Reactions of Tetrakis(Dimethylamino)Ethylene with Weak Acids.
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)
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 01, 1972
- Accession Number
- AD0904111
Entities
People
- William P. Norris
Organizations
- Naval Air Weapons Station China Lake